Table of Contents
ISRN Spectroscopy
Volume 2013, Article ID 287353, 29 pages
http://dx.doi.org/10.1155/2013/287353
Review Article

Platinum and Palladium Polyamine Complexes as Anticancer Agents: The Structural Factor

Research Unit “Molecular Physical Chemistry,” Department of Life Sciences, Faculty of Science and Technology, University of Coimbra, Apartado 3046, 3001-401 Coimbra, Portugal

Received 13 November 2012; Accepted 11 December 2012

Academic Editors: J. Casado, A. A. Ensafi, and M. Mączka

Copyright © 2013 M. P. M. Marques. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. G. M. Cragg, P. G. Grothaus, and D. J. Newman, “Impact of natural products on developing new anti-cancer agents,” Chemical Reviews, vol. 109, no. 7, pp. 3012–3043, 2009. View at Publisher · View at Google Scholar · View at Scopus
  2. A. E. Pegg, “Polyamine metabolism and its importance in neoplastic growth and as a target for chemotherapy,” Cancer Research, vol. 48, no. 4, pp. 759–774, 1988. View at Google Scholar · View at Scopus
  3. H. Köpf and P. Köpf-Maier, “Titanocene dichloride–the first metallocene with cancerostatic activity,” Angewandte Chemie, vol. 18, no. 6, pp. 477–478, 1979. View at Google Scholar · View at Scopus
  4. T. Rau and R. van Eldik, Metal Ions in Biological Systems, New York, NY, USA, 1996.
  5. C. Orvig and M. J. Abrams, “Medicinal inorganic chemistry: introduction,” Chemical Reviews, vol. 99, no. 9, pp. 2202–2203, 1999. View at Google Scholar · View at Scopus
  6. C. S. Allardyce, A. Dorcier, C. Scolaro, and P. J. Dyson, “Development of organometallic (organo-transition metal) pharmaceuticals,” Applied Organometallic Chemistry, vol. 19, no. 1, pp. 1–10, 2005. View at Publisher · View at Google Scholar · View at Scopus
  7. P. J. Dyson and G. Sava, “Metal-based antitumour drugs in the post genomic era,” Dalton Transactions, no. 16, pp. 1929–1933, 2006. View at Publisher · View at Google Scholar · View at Scopus
  8. K. B. Garbutcheon-Singh, M. P. Grant, B. W. Harper et al., “Transition metal based anticancer drugs,” Current Topics in Medicinal Chemistry, vol. 11, no. 5, pp. 521–542, 2011. View at Publisher · View at Google Scholar · View at Scopus
  9. S. Gomez-Ruiz, D. Maksimovic-Ivanic, S. Mijatovic, and G. N. Kaluderovic, “On the discovery, biological effects, and use of cisplatin and metallocenes in anticancer chemotherapy,” Bioinorganic Chemistry and Applications, vol. 2012, Article ID 140284, 14 pages, 2012. View at Publisher · View at Google Scholar
  10. M. Gielen, Metal Based Antitumor Drugs, Freud, London, UK, 1988.
  11. N. Farrell, Uses of Inorganic Chemistry in Medicine, Royal Society of Chemistry, Cambridge, UK, 1999.
  12. S. P. Fricker, “Metal based drugs: from serendipity to design,” Dalton Transactions, no. 43, pp. 4903–4917, 2007. View at Publisher · View at Google Scholar · View at Scopus
  13. M. J. Hannon, “Metal-based anticancer drugs: from a past anchored in platinum chemistry to a post-genomic future of diverse chemistry and biology,” Pure and Applied Chemistry, vol. 79, no. 12, pp. 2243–2261, 2007. View at Publisher · View at Google Scholar · View at Scopus
  14. S. H. van Rijt and P. J. Sadler, “Current applications and future potential for bioinorganic chemistry in the development of anticancer drugs,” Drug Discovery Today, vol. 14, no. 23-24, pp. 1089–1097, 2009. View at Publisher · View at Google Scholar · View at Scopus
  15. N. Farrell, “Polynuclear platinum drugs,” in Metal Complexes in Tumor Diagnosis and as Anticancer Agents, pp. 251–296, 2004. View at Google Scholar
  16. M. Galanski, V. B. Arion, M. A. Jakupec, and B. K. Keppler, “Recent developments in the field of tumor-inhibiting metal complexes,” Current Pharmaceutical Design, vol. 9, no. 25, pp. 2078–2089, 2003. View at Publisher · View at Google Scholar · View at Scopus
  17. B. Rosenberg, L. Vancamp, and T. Krigas, “Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode,” Nature, vol. 205, no. 4972, pp. 698–699, 1965. View at Publisher · View at Google Scholar · View at Scopus
  18. B. Rosenberg, L. Vancamp, J. E. Trosko, and V. H. Mansour, “Platinum compounds: a new class of potent antitumour agents,” Nature, vol. 222, no. 5191, pp. 385–386, 1969. View at Publisher · View at Google Scholar · View at Scopus
  19. B. Rosenberg and L. VanCamp, “The successful regression of large solid sarcoma 180 tumors by platinum compounds,” Cancer Research, vol. 30, no. 6, pp. 1799–1802, 1970. View at Google Scholar · View at Scopus
  20. M. Shimizu and B. Rosenberg, “A similar action to UV irradiation and a preferential inhibition of DNA synthesis in E. coli by antitumor platinum compounds,” Journal of Antibiotics, vol. 26, no. 4, pp. 243–245, 1973. View at Google Scholar · View at Scopus
  21. B. Rosenberg, “Platinum complexes for the treatment of cancer: why the search goes on?” in CisplatIn, pp. 1–27, Verlag Helvetica Chimica Acta, 1999. View at Google Scholar
  22. O. Heby and L. Persson, “Molecular genetics of polyamine synthesis in eukaryotic cells,” Trends in Biochemical Sciences, vol. 15, no. 4, pp. 153–158, 1990. View at Google Scholar · View at Scopus
  23. A. Tamori, S. Nishiguchi, T. Kuroki et al., “Point mutation of ornithine decarboxylase gene in human hepatocellular carcinoma,” Cancer Research, vol. 55, no. 16, pp. 3500–3503, 1995. View at Google Scholar · View at Scopus
  24. M. Auvinen, A. Paasinen, L. C. Andersson, and E. Holtta, “Ornithine decarboxylase activity is critical for cell transformation,” Nature, vol. 360, no. 6402, pp. 355–358, 1992. View at Publisher · View at Google Scholar · View at Scopus
  25. J. Janne, L. Alhonen, and P. Leinonen, “Polyamines: from molecular biology to clinical applications,” Annals of Medicine, vol. 23, no. 3, pp. 241–259, 1991. View at Google Scholar · View at Scopus
  26. K. Nishioka, Polyamines in Cancer: Basic Mechanisms and Clinical Approaches, Springer, Berlin, Germany, 1966.
  27. A. Bonetti, T. Franceschi, P. Apostoli et al., “Cisplatin pharmacokinetics using a five-day schedule during repeated courses of chemotherapy in germ cell tumors,” Therapeutic Drug Monitoring, vol. 17, no. 1, pp. 25–32, 1995. View at Google Scholar · View at Scopus
  28. M. Lehman and G. Thomas, “Is concurrent chemotherapy and radiotherapy the new standard of care for locally advanced cervical cancer?” International Journal of Gynecological Cancer, vol. 11, no. 2, pp. 87–99, 2001. View at Publisher · View at Google Scholar · View at Scopus
  29. P. J. Loehrer and L. H. Einhorn, “Drugs 5 years later—cisplatin,” Annals of Internal Medicine, vol. 100, no. 5, pp. 704–713, 1984. View at Google Scholar · View at Scopus
  30. R. F. Ozols, “Current status of chemotherapy for ovarian cancer,” Seminars in Oncology, vol. 22, no. 5, pp. 61–66, 1995. View at Google Scholar · View at Scopus
  31. A. L. Pinto and S. J. Lippard, “Binding of the antitumor drug cis-diamminedichloroplatinum(II) (cisplatin) to DNA,” Biochimica et Biophysica Acta, vol. 780, no. 3, pp. 167–180, 1985. View at Publisher · View at Google Scholar · View at Scopus
  32. J. L. Vanderveer and J. Reedijk, “Investigating antitumour drug mechanisms,” Chemistry in Britain, vol. 24, no. 8, pp. 775–780, 1988. View at Google Scholar
  33. N. P. Johnson, J.-L. Butour, G. Villani et al., “Metal antitumor compounds: the mechanism of action of platinum complexes,” Progress in Clinical Biochemistry and Medicine, vol. 10, pp. 1–24, 1989. View at Google Scholar
  34. P. M. Takahara, C. A. Frederick, and S. J. Lippard, “Crystal structure of the anticancer drug cisplatin bound to duplex DNA,” Journal of the American Chemical Society, vol. 118, no. 49, pp. 12309–12321, 1996. View at Publisher · View at Google Scholar · View at Scopus
  35. T. W. Hambley, “Platinum binding to DNA: structural controls and consequences,” Journal of the Chemical Society, Dalton Transactions, no. 19, pp. 2711–2718, 2001. View at Google Scholar · View at Scopus
  36. R. N. Bose, “Biomolecular targets for platinum antitumor drugs,” Mini Reviews in Medicinal Chemistry, vol. 2, no. 2, pp. 103–111, 2002. View at Google Scholar · View at Scopus
  37. J. Reedijk, “New clues for platinum antitumor chemistry: kinetically controlled metal binding to DNA,” Proceedings of the National Academy of Sciences of the United States of America, vol. 100, no. 7, pp. 3611–3616, 2003. View at Publisher · View at Google Scholar · View at Scopus
  38. D. Wang and S. J. Lippard, “Cellular processing of platinum anticancer drugs,” Nature Reviews Drug Discovery, vol. 4, no. 4, pp. 307–320, 2005. View at Publisher · View at Google Scholar · View at Scopus
  39. Y. Jung and S. J. Lippard, “Direct cellular responses to platinum-induced DNA damage,” Chemical Reviews, vol. 107, no. 5, pp. 1387–1407, 2007. View at Publisher · View at Google Scholar · View at Scopus
  40. A. M. Pizarro and P. J. Sadler, “Unusual DNA binding modes for metal anticancer complexes,” Biochimie, vol. 91, no. 10, pp. 1198–1211, 2009. View at Publisher · View at Google Scholar · View at Scopus
  41. Y. P. Ho, S. C. F. Au-Yeung, and K. K. W. To, “Platinum-based anticancer agents: innovative design strategies and biological perspectives,” Medicinal Research Reviews, vol. 23, no. 5, pp. 633–655, 2003. View at Publisher · View at Google Scholar · View at Scopus
  42. J. T. Hartmann and H. P. Lipp, “Toxicity of platinum compounds,” Expert Opinion on Pharmacotherapy, vol. 4, no. 6, pp. 889–901, 2003. View at Publisher · View at Google Scholar · View at Scopus
  43. S. Raguz and E. Yagüe, “Resistance to chemotherapy: new treatments and novel insights into an old problem,” British Journal of Cancer, vol. 99, no. 3, pp. 387–391, 2008. View at Publisher · View at Google Scholar · View at Scopus
  44. X. Yao, K. Panichpisal, N. Kurtzman, and K. Nugent, “Cisplatin nephrotoxicity: a review,” The American Journal of the Medical Sciences, vol. 334, no. 2, pp. 115–124, 2007. View at Publisher · View at Google Scholar · View at Scopus
  45. A. M. Florea and D. Büsselberg, “Cisplatin as an anti-tumor drug: cellular mechanisms of activity, drug resistance and induced side effects,” Cancers, vol. 3, no. 1, pp. 1351–1371, 2011. View at Publisher · View at Google Scholar · View at Scopus
  46. T. Boulikas and M. Vougiouka, “Cisplatin and platinum drugs at the molecular level,” Oncology reports, vol. 10, no. 6, pp. 1663–1682, 2003. View at Google Scholar · View at Scopus
  47. G. Momekov and D. Momekova, “Recent developments in antitumor platinum coordination compounds,” Expert Opinion on Therapeutic Patents, vol. 16, no. 10, pp. 1383–1403, 2006. View at Publisher · View at Google Scholar · View at Scopus
  48. L. Kelland, “The resurgence of platinum-based cancer chemotherapy,” Nature Reviews Cancer, vol. 7, no. 8, pp. 573–584, 2007. View at Publisher · View at Google Scholar · View at Scopus
  49. N. J. Wheate, S. Walker, G. E. Craig, and R. Oun, “The status of platinum anticancer drugs in the clinic and in clinical trials,” Dalton Transactions, vol. 39, no. 35, pp. 8113–8127, 2010. View at Publisher · View at Google Scholar · View at Scopus
  50. X. Wang, “Fresh platinum complexes with promising antitumor activity,” Anti-Cancer Agents in Medicinal Chemistry, vol. 10, no. 5, pp. 396–411, 2010. View at Google Scholar · View at Scopus
  51. U. Olszewski and G. Hamilton, “A better platinum-based anticancer drug yet to come?” Anti-Cancer Agents in Medicinal Chemistry, vol. 10, no. 4, pp. 293–301, 2010. View at Google Scholar · View at Scopus
  52. S. Komeda, T. Moulaei, M. Chikuma et al., “The phosphate clamp: a small and independent motif for nucleic acid backbone recognition,” Nucleic Acids Research, vol. 39, no. 1, pp. 325–336, 2011. View at Publisher · View at Google Scholar · View at Scopus
  53. C. Monneret, “Platinum anticancer drugs. From serendipity to rational design,” Annales Pharmaceutiques Françaises, vol. 69, no. 6, pp. 286–295, 2011. View at Publisher · View at Google Scholar
  54. P. C. Bruijnincx and P. J. Sadler, “New trends for metal complexes with anticancer activity,” Current Opinion in Chemical Biology, vol. 12, no. 2, pp. 197–206, 2008. View at Publisher · View at Google Scholar · View at Scopus
  55. S. San-Marina, R. Gupta, and I. Iosif, “Computational strategies for drug reprofiling,” Journal of Proteomics and Bioinformatics, vol. 4, no. 11, pp. 242–244, 2011. View at Google Scholar
  56. R. B. Weiss and M. C. Christian, “New cisplatin analogues in development: a review,” Drugs, vol. 46, no. 3, pp. 360–377, 1993. View at Google Scholar · View at Scopus
  57. I. Ott and R. Gust, “Preclinical and clinical studies on the use of platinum complexes for breast cancer treatment,” Anti-Cancer Agents in Medicinal Chemistry, vol. 7, no. 1, pp. 95–110, 2007. View at Publisher · View at Google Scholar · View at Scopus
  58. R. Williams, “Discontinued drugs in 2010: oncology drugs,” Expert Opinion on Investigational Drugs, vol. 20, no. 11, pp. 1479–1496, 2011. View at Google Scholar
  59. S. A. S. Ghazanfar, J. T. Edsall, and D. V. Myers, “Raman spectra of diamines and diammonium ions: effects of ionization on carbon-hydrogen stretching frequencies,” Journal of the American Chemical Society, vol. 86, no. 4, pp. 559–564, 1964. View at Google Scholar · View at Scopus
  60. A. Bertoluzza, C. Fagnano, P. Finelli, M. A. Morelli, R. Simoni, and R. Tosi, “Raman and infrared-spectra of spermidine and spermine and their hydrochlorides and phosphates as a basis for the study of the interactions between polyamines and nucleic-acids,” Journal of Raman Spectroscopy, vol. 14, no. 6, pp. 386–394, 1983. View at Publisher · View at Google Scholar
  61. L. A. E. Batista de Carvalho, A. M. Amorim da Costa, M. L. Duarte, and J. J. C. Teixeira-Dias, “Conformational studies of n-propylamine by combined ab initio MO calculations and Raman spectroscopy,” Spectrochimica Acta Part A: Molecular Spectroscopy, vol. 44, no. 7, pp. 723–732, 1988. View at Google Scholar · View at Scopus
  62. L. A. E. Batista de Carvalho, A. M. Amorim da Costa, and J. J. C. Teixeira-Dias, “A comparative ab initio MO study of internal rotations in ethylamine and n-propylamine,” Journal of Molecular Structure: THEOCHEM, vol. 205, no. C, pp. 327–351, 1990. View at Google Scholar · View at Scopus
  63. L. A. E. Batista de Carvalho, J. J. C. Teixeira-Dias, and R. Fausto, “A molecular mechanics force field for conformational analysis of aliphatic acyclic amines,” Structural Chemistry, vol. 1, no. 6, pp. 533–542, 1990. View at Publisher · View at Google Scholar · View at Scopus
  64. L. A. E. Batista de Carvalho, L. E. Lourenço, and M. P. M. Marques, “Conformational study of 1,2-diaminoethane by combined ab initio MO calculations and Raman spectroscopy,” Journal of Molecular Structure, vol. 482-483, pp. 639–646, 1999. View at Publisher · View at Google Scholar · View at Scopus
  65. M. P. M. Marques and L. A. E. Batista de Carvalho, “Theoretical approach to the conformational preferences of putrescine,” in Cost 917: Biogenically Active Amines in Food, pp. 122–129, European Communities, Luxembourg, 2000. View at Google Scholar
  66. M. P. M. Marques, L. A. E. Batista de Carvalho, and J. Tomkinson, “Study of biogenic and α,ω-polyamines by combined inelastic neutron scattering and Raman spectroscopies and by ab initio molecular orbital calculations,” The Journal of Physical Chemistry A, vol. 106, no. 11, pp. 2473–2482, 2002. View at Publisher · View at Google Scholar · View at Scopus
  67. A. M. Amorim da Costa, M. P. M. Marques, and L. A. E. Batista de Carvalho, “The carbon-hydrogen stretching region of the Raman spectra of 1,6-hexanediamine: N-deuteration, ionisation and temperature effects,” Vibrational Spectroscopy, vol. 29, no. 1-2, pp. 61–67, 2002. View at Publisher · View at Google Scholar · View at Scopus
  68. A. M. Amorim da Costa, M. P. M. Marques, and L. A. E. Batista de Carvalho, “Raman spectra of putrescine, spermidine and spermine polyamines and their N-deuterated and N-ionized derivatives,” Journal of Raman Spectroscopy, vol. 34, no. 5, pp. 357–366, 2003. View at Publisher · View at Google Scholar · View at Scopus
  69. A. M. Amorim da Costa, M. P. M. Marques, and L. A. E. Batista de Carvalho, “Intra- versus interchain interactions in α,ω-polyamines: a Raman spectroscopy study,” Vibrational Spectroscopy, vol. 35, no. 1-2, pp. 165–171, 2004. View at Publisher · View at Google Scholar · View at Scopus
  70. A. M. Amado, J. C. Otero, M. P. M. Marques, and L. A. E. Batista de Carvalho, “Spectroscopic and theoretical studies on solid 1,2-ethylenediamine dihydrochloride salt,” ChemPhysChem, vol. 5, no. 12, pp. 1837–1847, 2004. View at Publisher · View at Google Scholar · View at Scopus
  71. L. A. E. Batista de Carvalho, M. P. M. Marques, and J. Tomkinson, “Transverse acoustic modes of biogenic and α,ω-polyamines: a study by inelastic neutron scattering and raman spectroscopies coupled to DFT calculations,” The Journal of Physical Chemistry A, vol. 110, no. 47, pp. 12947–12954, 2006. View at Publisher · View at Google Scholar · View at Scopus
  72. M. P. M. Marques and L. A. E. Batista de Carvalho, “Vibrational spectroscopy studies on linear polyamines,” Biochemical Society Transactions, vol. 35, no. 2, pp. 374–380, 2007. View at Publisher · View at Google Scholar · View at Scopus
  73. E. W. Gerner and F. L. Meyskens, “Polyamines and cancer: old molecules, new understanding,” Nature Reviews Cancer, vol. 4, no. 10, pp. 781–792, 2004. View at Publisher · View at Google Scholar · View at Scopus
  74. E. Agostinelli, M. P. M. Marques, R. Calheiros et al., “Polyamines: fundamental characters in chemistry and biology,” Amino Acids, vol. 38, no. 2, pp. 393–403, 2010. View at Publisher · View at Google Scholar · View at Scopus
  75. C. W. Porter, R. J. Bernacki, J. Miller, and R. J. Bergeron, “Antitumor activity of N1,N11-bis(ethyl)norspermine against human melanoma xenografts and possible biochemical correlates of drug action,” Cancer Research, vol. 53, no. 3, pp. 581–586, 1993. View at Google Scholar · View at Scopus
  76. R. A. Casero and P. M. Woster, “Recent advances in the development of polyamine analogues as antitumor agents,” Journal of Medicinal Chemistry, vol. 52, no. 15, pp. 4551–4573, 2009. View at Publisher · View at Google Scholar · View at Scopus
  77. T. M. Silva, S. Oredsson, L. Persson, P. Woster, and M. P. Marques, “Novel Pt(II) and Pd(II) complexes with polyamine analogues: synthesis and vibrational analysis,” Journal of Inorganic Biochemistry, vol. 108, pp. 1–7, 2012. View at Publisher · View at Google Scholar
  78. N. Seiler, “Thirty years of polyamine-related approaches to cancer therapy. Retrospect and prospect. Part 2. Structural analogues and derivatives,” Current Drug Targets, vol. 4, no. 7, pp. 565–585, 2003. View at Publisher · View at Google Scholar · View at Scopus
  79. N. P. Farrell, S. G. de Almeida, and K. A. Skov, “Bis(platinum) complexes containing two platinum cis-diammine units. Synthesis and initial DNA-binding studies,” Journal of the American Chemical Society, vol. 110, no. 15, pp. 5018–5019, 1988. View at Google Scholar · View at Scopus
  80. N. Farrell, Y. Qu, L. Feng, and B. van Houten, “Comparison of chemical reactivity, cytotoxicity, interstrand cross-linking and DNA sequence specificity of bis(platinum) complexes containing monodentate or bidentate coordination spheres with their monomeric analogues,” Biochemistry, vol. 29, no. 41, pp. 9522–9531, 1990. View at Google Scholar · View at Scopus
  81. N. Farrell, “Nonclassical platinum antitumor agents: perspectives for design and development of new drugs complementary to cisplatin,” Cancer Investigation, vol. 11, no. 5, pp. 578–589, 1993. View at Google Scholar · View at Scopus
  82. H. Rauter, R. Di Domenico, E. Mental, A. Oliva, Y. Qu, and N. Farrell, “Selective platination of biologically relevant polyamines. Linear coordinating spermidine and spermine as amplifying linkers in dinuclear platinum complexes,” Inorganic Chemistry, vol. 36, no. 18, pp. 3919–3927, 1997. View at Google Scholar · View at Scopus
  83. N. Farrell, “DNA binding of nonclassical platinum antitumor complexes,” in Advances in DNA Sequence-Specific Agents, pp. 179–199, Elsevier, Philadelphia, Pa, USA, 1998. View at Google Scholar
  84. V. Brabec, J. Kašpárková, O. Vrána et al., “DNA modifications by a novel bifunctional trinuclear platinum Phase I anticancer agent,” Biochemistry, vol. 38, no. 21, pp. 6781–6790, 1999. View at Publisher · View at Google Scholar · View at Scopus
  85. N. Farrell, “Polynuclear charged platinum compounds as a new class of anticancer agents. Toward a new paradigm,” in Platinum-Based Drugs in Cancer Therapy, Human Press, Totowa, NJ, USA, 2000. View at Google Scholar
  86. C. Manzotti, G. Pratesi, E. Menta et al., “BBR 3464: a novel triplatinum complex, exhibiting a preclinical profile of antitumor efficacy different from cisplatin,” Clinical Cancer Research, vol. 6, no. 7, pp. 2626–2634, 2000. View at Google Scholar · View at Scopus
  87. A. S. Abu-Surrah and M. Kettunen, “Platinum group antitumor chemistry: design and development of new anticancer drugs complementary to cisplatin,” Current Medicinal Chemistry, vol. 13, no. 11, pp. 1337–1357, 2006. View at Publisher · View at Google Scholar · View at Scopus
  88. A. S. Abu-Surrah, H. H. Al-Sa’doni, and M. Y. Abdalla, “Palladium-based chemotherapeutic agents: routes toward complexes with good antitumor activity,” Cancer Therapy, vol. 6, pp. 1–10, 2008. View at Google Scholar
  89. A. Hegmans, S. J. Berners-Price, M. S. Davies, D. S. Thomas, A. S. Humphreys, and N. Farrell, “Long range 1,4 and 1,6-interstrand cross-links formed by a trinuclear platinum complex. Minor groove preassociation affects kinetics and mechanism of cross-link formation as well as adduct structure,” Journal of the American Chemical Society, vol. 126, no. 7, pp. 2166–2180, 2004. View at Publisher · View at Google Scholar · View at Scopus
  90. M. L. González, J. M. Tercero, A. Matilla et al., “Cis-dichloro(α,ω-diamino carboxylate ethyl ester)palladium(II) as palladium(II) versus platinum(II) model anticancer drugs: synthesis, solution equilibria of their aqua, hydroxo, and/or chloro species, and in vitro/in vivo DNA-binding properties,” Inorganic Chemistry, vol. 36, no. 9, pp. 1806–1812, 1997. View at Google Scholar · View at Scopus
  91. B. B. Zmejkovski, G. N. Kaluderović, S. Gómez-Ruiz et al., “Palladium(II) complexes with R2edda-derived ligands. Part II. Synthesis, characterization and in vitro antitumoral studies of R2eddip esters and palladium(II) complexes,” European Journal of Medicinal Chemistry, vol. 44, no. 9, pp. 3452–3458, 2009. View at Publisher · View at Google Scholar · View at Scopus
  92. J. M. Vujić, M. Cvijović, G. N. Kaluerović et al., “Palladium(II) complexes with R2edda derived ligands. Part IV. O,O-dialkyl esters of (S,S)-ethylenediamine-N,N-di-2-(4-methyl)- pentanoic acid dihydrochloride and their palladium(II) complexes: synthesis, characterization and in vitro antitumoral activity against chronic lymphocytic leukemia (CLL) cells,” European Journal of Medicinal Chemistry, vol. 45, no. 9, pp. 3601–3606, 2010. View at Publisher · View at Google Scholar · View at Scopus
  93. G. Zhao, H. Lin, P. Yu et al., “Ethylenediamine-palladium(II) complexes with pyridine and its derivatives: synthesis, molecular structure and initial antitumor studies,” Journal of Inorganic Biochemistry, vol. 73, no. 3, pp. 145–149, 1999. View at Publisher · View at Google Scholar · View at Scopus
  94. N. Jain, R. Mittal, T. S. Srivastava, K. Satyamoorthy, and M. P. Chitnis, “Synthesis, characterization, DNA binding, and cytotoxic studies of dinuclear complexes of palladium(II) and platinum(II) with 2,2-bipyridine and α,ω-diaminoalkane-N,N-diacetic acid,” Journal of Inorganic Biochemistry, vol. 53, no. 2, pp. 79–94, 1994. View at Publisher · View at Google Scholar · View at Scopus
  95. G. Zhao, H. Lin, S. Zhu, H. Sun, and Y. Chen, “Dinuclear palladium(II) complexes containing two monofunctional [Pd(en)(pyridine)Cl]+ units bridged by Se or S. Synthesis, characterization, cytotoxicity and kinetic studies of DNA-binding,” Journal of Inorganic Biochemistry, vol. 70, no. 3-4, pp. 219–226, 1998. View at Publisher · View at Google Scholar · View at Scopus
  96. G. Faraglia, D. Fregona, S. Sitran et al., “Platinum(II) and palladium(II) complexes with dithiocarbamates and amines: synthesis, characterization and cell assay,” Journal of Inorganic Biochemistry, vol. 83, no. 1, pp. 31–40, 2001. View at Publisher · View at Google Scholar · View at Scopus
  97. A. I. Anzellotti, M. Sabat, and N. Farrell, “Covalent and noncovalent interactions for [metal(dien)nucleobase] 2+ complexes with L-tryptophan derivatives: formation of palladium-tryptophan species by nucleobase substitution under biologically relevant conditions,” Inorganic Chemistry, vol. 45, no. 4, pp. 1638–1645, 2006. View at Publisher · View at Google Scholar · View at Scopus
  98. I. Kostova, “Platinum complexes as anticancer agents,” Recent Patents on Anti-Cancer Drug Discovery, vol. 1, no. 1, pp. 1–22, 2006. View at Publisher · View at Google Scholar · View at Scopus
  99. N. P. Farrell, “Platinum formulations as anticancer drugs clinical and pre-clinical studies,” Current Topics in Medicinal Chemistry, vol. 11, no. 21, pp. 2623–2631, 2011. View at Publisher · View at Google Scholar
  100. S. Ahmad, A. A. Isab, and S. Ali, “Structural and mechanistic aspects of platinum anticancer agents,” Transition Metal Chemistry, vol. 31, no. 8, pp. 1003–1016, 2006. View at Publisher · View at Google Scholar · View at Scopus
  101. J. E. Rosenberg, V. K. Weinberg, W. K. Kelly et al., “Activity of second-line chemotherapy in docetaxel-refractory hormone-refractory prostate cancer patients: randomized phase 2 study of ixabepilone or mitoxantrone and prednisone,” Cancer, vol. 110, no. 3, pp. 556–563, 2007. View at Publisher · View at Google Scholar · View at Scopus
  102. S. Komeda, “Unique platinum-DNA interactions may lead to more effective platinum-based antitumor drugs,” Metallomics, vol. 3, no. 7, pp. 650–655, 2011. View at Publisher · View at Google Scholar · View at Scopus
  103. M. M. Regan, E. K. O'Donnell, W. K. Kelly et al., “Efficacy of carboplatin-taxane combinations in the management of castration-resistant prostate cancer: a pooled analysis of seven prospective clinical trials,” Annals of Oncology, vol. 21, no. 2, pp. 312–318, 2010. View at Publisher · View at Google Scholar · View at Scopus
  104. S. S. Hah, K. M. Stivers, R. W. de Vere White, and P. T. Henderson, “Kinetics of carboplatin-DNA binding in genomic DNA and bladder cancer cells as determined by accelerator mass spectrometry,” Chemical Research in Toxicology, vol. 19, no. 5, pp. 622–626, 2006. View at Publisher · View at Google Scholar · View at Scopus
  105. Y. Kidani, K. Inagaki, R. Saito, and S. Tsukagoshi, “Synthesis and anti tumor activities of platinum (II) complexes of 1,2 diaminocyclohexane isomers and their related derivatives,” Journal of Clinical Hematology and Oncology, vol. 7, no. 1, pp. 197–209, 1977. View at Google Scholar · View at Scopus
  106. Y. Kidani, M. Noji, and T. Tashiro, “Antitumor activity of platinum(II) complexes of 1,2-diamino-cyclohexane isomers,” Gann, vol. 71, no. 5, pp. 637–643, 1980. View at Google Scholar · View at Scopus
  107. E. Raymond, S. Faivre, S. Chaney, J. Woynarowski, and E. Cvitkovic, “Cellular and molecular pharmacology of oxaliplatin,” Molecular Cancer Therapeutics, vol. 1, no. 3, pp. 227–235, 2002. View at Google Scholar · View at Scopus
  108. B. Spingler, D. A. Whittington, and S. J. Lippard, “2.4 Å crystal structure of an oxaliplatin 1,2-d(GpG) intrastrand Cross-link in a DNA dodecamer duplex,” Inorganic Chemistry, vol. 40, no. 22, pp. 5596–5602, 2001. View at Publisher · View at Google Scholar · View at Scopus
  109. T. A. K. Al-Allaf, L. J. Rashan, D. Steinborn, K. Merzweiler, and C. Wagner, “Platinum(II) and palladium(II) complexes analogous to oxaliplatin with different cyclohexyldicarboxylate isomeric anions and their in vitro antitumour activity. Structural elucidation of [Pt(C2O4)(cis-dach)],” Transition Metal Chemistry, vol. 28, no. 6, pp. 717–721, 2003. View at Publisher · View at Google Scholar · View at Scopus
  110. M. Galanski, A. Yasemi, S. Slaby et al., “Synthesis, crystal structure and cytotoxicity of new oxaliplatin analogues indicating that improvement of anticancer activity is still possible,” European Journal of Medicinal Chemistry, vol. 39, no. 8, pp. 707–714, 2004. View at Publisher · View at Google Scholar · View at Scopus
  111. M. Noji, R. Kizu, Y. Takeda et al., “Preparation of antitumor oxaliplatin/cisplatin docking dinuclear platinum complex,” Biomedicine & Pharmacotherapy, vol. 59, no. 5, pp. 224–229, 2005. View at Publisher · View at Google Scholar · View at Scopus
  112. A. Bhargava and U. N. Vaishampayan, “Satraplatin: leading the new generation of oral platinum agents,” Expert Opinion on Investigational Drugs, vol. 18, no. 11, pp. 1787–1797, 2009. View at Publisher · View at Google Scholar · View at Scopus
  113. L. R. Kelland, “An update on satraplatin: the first orally available platinum anticancer drug,” Expert Opinion on Investigational Drugs, vol. 9, no. 6, pp. 1373–1382, 2000. View at Google Scholar · View at Scopus
  114. L. Kelland, “Broadening the clinical use of platinum drug-based chemotherapy with new analogues: satraplatin and picoplatin,” Expert Opinion on Investigational Drugs, vol. 16, no. 7, pp. 1009–1021, 2007. View at Publisher · View at Google Scholar · View at Scopus
  115. H. Choy, C. Park, and M. Yao, “Current status and future prospects for satraplatin, an oral platinum analogue,” Clinical Cancer Research, vol. 14, no. 6, pp. 1633–1638, 2008. View at Publisher · View at Google Scholar · View at Scopus
  116. E. Fokkema, H. J. M. Groen, M. N. Helder, E. G. E. de Vries, and C. Meijer, “JM216-, JM118-, and cisplatin-induced cytotoxicity in relation to platinum-DNA adduct formation, glutathione levels and p53 status in human tumour cell lines with different sensitivities to cisplatin,” Biochemical Pharmacology, vol. 63, no. 11, pp. 1989–1996, 2002. View at Publisher · View at Google Scholar · View at Scopus
  117. C. Sessa, C. Minoia, A. Ronchi et al., “Phase I clinical and pharmacokinetic study of the oral platinum analogue JM216 given daily for 14 days,” Annals of Oncology, vol. 9, no. 12, pp. 1315–1322, 1998. View at Publisher · View at Google Scholar · View at Scopus
  118. M. Kalimutho, A. Minutolo, S. Grelli et al., “Satraplatin (JM-216) mediates G2/M cell cycle arrest and potentiates apoptosis via multiple death pathways in colorectal cancer cells thus overcoming platinum chemo-resistance,” Cancer Chemotherapy and Pharmacology, vol. 67, no. 6, pp. 1299–1312, 2011. View at Publisher · View at Google Scholar · View at Scopus
  119. G. Samimi and S. B. Howell, “Modulation of the cellular pharmacology of JM118, the major metabolite of satraplatin, by copper influx and efflux transporters,” Cancer Chemotherapy and Pharmacology, vol. 57, no. 6, pp. 781–788, 2006. View at Publisher · View at Google Scholar · View at Scopus
  120. C. N. Sternberg, D. P. Petrylak, O. Sartor et al., “Multinational, double-blind, phase III study of prednisone and either satraplatin or placebo in patients with castrate-refractory prostate cancer progressing after prior chemotherapy: the SPARC trial,” Journal of Clinical Oncology, vol. 27, no. 32, pp. 5431–5438, 2009. View at Publisher · View at Google Scholar · View at Scopus
  121. D. P. Petrylak, O. Sartor, J. Witjes et al., “A phase iii, randomized, double-blind trial of satraplatin and prednisone vs placebo and prednisone for patients with hormone refractory prostate cancer (HRPC),” in Proceedings of Prostate Cancer Symposium, 2007.
  122. J. Holford, F. Raynaud, B. A. Murrer et al., “Chemical, biochemical and pharmacological activity of the novel sterically hindered platinum co-ordination complex, cis-[amminedichloro(2-methylpyridine)] platinum(II) (AMD473),” Anti-Cancer Drug Design, vol. 13, no. 1, pp. 1–18, 1998. View at Google Scholar · View at Scopus
  123. P. Beale, I. Judson, A. O'Donnell et al., “A phase I clinical and pharmacological study of cis-diamminedichloro(2-methylpyridine) platinum II (AMD473),” British Journal of Cancer, vol. 88, no. 7, pp. 1128–1134, 2003. View at Publisher · View at Google Scholar · View at Scopus
  124. A. R. Battle, R. Choi, D. E. Hibbs, and T. W. Hambley, “Platinum(IV) analogues of AMD473 (cis-[PtCl2(NH3)(2-picoline)]): preparative, structural, and electrochemical studies,” Inorganic Chemistry, vol. 45, no. 16, pp. 6317–6322, 2006. View at Publisher · View at Google Scholar · View at Scopus
  125. Y. Chen, Z. J. Guo, S. Parsons, and P. J. Sadler, “Stereospecific and kinetic control over the hydrolysis of a sterically hindered platinum picoline anticancer complex,” Chemistry, vol. 4, no. 4, pp. 672–676, 1998. View at Publisher · View at Google Scholar
  126. J. Holford, S. Y. Sharp, B. A. Murrer, M. Abrams, and L. R. Kelland, “In vitro circumvention of cisplatin resistance by the novel sterically hindered platinum complex AMD473,” British Journal of Cancer, vol. 77, no. 3, pp. 366–373, 1998. View at Google Scholar · View at Scopus
  127. K. A. Gelmon, D. Stewart, K. N. Chi et al., “A phase I study of AMD473 and docetaxel given once every 3 weeks in patients with advanced refractory cancer: a national cancer institute of Canada-clinical trials group trial, IND 131,” Annals of Oncology, vol. 15, no. 7, pp. 1115–1122, 2004. View at Publisher · View at Google Scholar · View at Scopus
  128. S. Y. Sharp, C. F. O'Neill, P. Rogers, F. E. Boxall, and L. R. Kelland, “Retention of activity by the new generation platinum agent AMD0473 in four human tumour cell lines possessing acquired resistance to oxaliplatin,” European Journal of Cancer, vol. 38, no. 17, pp. 2309–2315, 2002. View at Publisher · View at Google Scholar · View at Scopus
  129. C. T. Research, “Poniard pharmaceuticals announces final top-line results from phase 1 trial demonstrating positive bioavailability with oral picoplatin,” in Oncology Business Week, 2008. View at Google Scholar
  130. P. Sood, K. Bruce Thurmond 2nd, J. E. Jacob et al., “Synthesis and characterization of AP5346, a novel polymer-linked diaminocyclohexyl platinum chemotherapeutic agent,” Bioconjugate Chemistry, vol. 17, no. 5, pp. 1270–1279, 2006. View at Publisher · View at Google Scholar · View at Scopus
  131. S. B. Howell, “The design and development of the tumor-targeting nanopolymer dach platinum conjugate ap5346,” in PlatInum and Other Heavy Metal Compounds in Cancer Chemotherapy, pp. 33–39, Humana Press, Totowa, NJ, USA, 2009. View at Google Scholar
  132. J. R. Rice, J. L. Gerberich, D. P. Nowotnik, and S. B. Howell, “Preclinical efficacy and pharmacokinetics of AP5346, a novel diaminocyclohexane-platinum tumor-targeting drug delivery system,” Clinical Cancer Research, vol. 12, no. 7, pp. 2248–2254, 2006. View at Publisher · View at Google Scholar · View at Scopus
  133. D. P. Nowotnik and E. Cvitkovic, “ProlindacTM (AP5346): a review of the development of an HPMA DACH platinum polymer therapeutic,” Advanced Drug Delivery Reviews, vol. 61, no. 13, pp. 1214–1219, 2009. View at Publisher · View at Google Scholar · View at Scopus
  134. D. P. Nowotnik, “AP5346 (ProLindac), a dach platinum polymer conjugate in Phase II trials against ovarian cancer,” Current Bioactive Compounds, vol. 7, no. 1, pp. 21–26, 2011. View at Publisher · View at Google Scholar · View at Scopus
  135. M. Campone, J. M. Rademaker-Lakhai, J. Bennouna et al., “Phase I and pharmacokinetic trial of AP5346, a DACH-platinum-polymer conjugate, administered weekly for three out of every 4 weeks to advanced solid tumor patients,” Cancer Chemotherapy and Pharmacology, vol. 60, no. 4, pp. 523–533, 2007. View at Publisher · View at Google Scholar · View at Scopus
  136. G. P. Stathopoulos, T. Boulikas, M. Vougiouka et al., “Pharmacokinetics and adverse reactions of a new liposomal cisplatin (Lipoplatin): phase I study,” Oncology Reports, vol. 13, no. 4, pp. 589–595, 2005. View at Google Scholar · View at Scopus
  137. D. B. Fenske and P. R. Cullis, “Liposomal nanomedicines,” Expert Opinion on Drug Delivery, vol. 5, no. 1, pp. 25–44, 2008. View at Publisher · View at Google Scholar · View at Scopus
  138. S. Bryde and A. I. P. M. de Kroon, “Nanocapsules of platinum anticancer drugs: development towards therapeutic use,” Future Medicinal Chemistry, vol. 1, no. 8, pp. 1467–1480, 2009. View at Publisher · View at Google Scholar · View at Scopus
  139. M. I. Koukourakis, A. Giatromanolaki, M. Pitiakoudis et al., “Concurrent liposomal cisplatin (Lipoplatin), 5-fluorouracil and radiotherapy for the treatment of locally advanced gastric cancer: a phase I/II study,” International Journal of Radiation Oncology Biology Physics, vol. 78, no. 1, pp. 150–155, 2010. View at Publisher · View at Google Scholar · View at Scopus
  140. N. Seetharamu, E. Kim, H. Hochster, F. Martin, and F. Muggia, “Phase II study of liposomal cisplatin (SPI-77) in platinum-sensitive recurrences of ovarian cancer,” Anticancer Research, vol. 30, no. 2, pp. 541–545, 2010. View at Google Scholar · View at Scopus
  141. G. P. Stathopoulos, T. Boulikas, A. Kourvetaris, and J. Stathopoulos, “Liposomal oxaliplatin in the treatment of advanced cancer: a phase I study,” Anticancer Research, vol. 26, no. 2 B, pp. 1489–1493, 2006. View at Google Scholar · View at Scopus
  142. T. Tippayamontri, R. Kotb, B. Paquette, and L. Sanche, “Cellular uptake and cytoplasm / DNA distribution of cisplatin and oxaliplatin and their liposomal formulation in human colorectal cancer cell HCT116,” Investigational New Drugs, vol. 29, no. 6, pp. 1321–1327, 2011. View at Publisher · View at Google Scholar · View at Scopus
  143. G. Charest, L. Sanche, D. Fortin, D. Mathieu, and B. Paquette, “Glioblastoma treatment: bypassing the toxicity of platinum compounds by using liposomal formulation and increasing treatment efficiency with concomitant radiotherapy,” International Journal of Radiation Oncology Biology Physics, vol. 84, no. 1, pp. 244–249, 2012. View at Publisher · View at Google Scholar
  144. I. Ali, Rahis-Uddin, K. Salim, M. A. Rather, W. A. Wani, and A. Haque, “Advances in nano drugs for cancer chemotherapy,” Current Cancer Drug Targets, vol. 11, no. 2, pp. 135–146, 2011. View at Publisher · View at Google Scholar · View at Scopus
  145. S. Qian, C. Li, and Z. Zuo, “Pharmacokinetics and disposition of various drug loaded liposomes,” Current Drug Metabolism, vol. 13, no. 4, pp. 372–395, 2012. View at Publisher · View at Google Scholar
  146. S. P. Sahane, A. K. Nikhar, S. Bhaskaran, and D. R. Mundhada, “Nanotechnology in cancer chemotherapy,” International Journal of Pharmacy and Technology, vol. 4, no. 2, pp. 2085–2099, 2012. View at Google Scholar
  147. T. Boulikas, “Low toxicity and anticancer activity of a novel liposomal cisplatin (lipoplatin) in mouse xenografts,” Oncology Reports, vol. 12, no. 1, pp. 3–12, 2004. View at Google Scholar · View at Scopus
  148. T. Boulikas, “Molecular mechanisms of cisplatin and its liposomally encapsulated form, lipoplatinTM. lipoplatinTM as a chemotherapy and antiangiogenesis drug,” Cancer Therapy, vol. 5, pp. 351–376, 2007. View at Google Scholar
  149. T. Boulikas, G. P. Stathopoulos, N. Volakakis, and M. Vougiouka, “Systemic lipoplatin infusion results in preferential tumor uptake in human studies,” Anticancer Research, vol. 25, no. 4, pp. 3031–3040, 2005. View at Google Scholar · View at Scopus
  150. C. M. Lee, T. Tanaka, T. Murai et al., “Novel chondroitin sulfate-binding cationic liposomes loaded with cisplatin efficiently suppress the local growth and liver metastasis of tumor cells in vivo,” Cancer Research, vol. 62, no. 15, pp. 4282–4288, 2002. View at Google Scholar · View at Scopus
  151. P. Devarajan, R. Tarabishi, J. Mishra et al., “Low renal toxicity of lipoplatin compared to cisplatin in animals,” Anticancer Research, vol. 24, no. 4, pp. 2193–2200, 2004. View at Google Scholar · View at Scopus
  152. C. Arienti, A. Tesei, A. Ravaioli et al., “Activity of lipoplatin in tumor and in normal cells in vitro,” Anti-Cancer Drugs, vol. 19, no. 10, pp. 983–990, 2008. View at Publisher · View at Google Scholar · View at Scopus
  153. T. Boulikas, “Clinical overview on lipoplatinTM: a successful liposomal formulation of cisplatin,” Expert Opinion on Investigational Drugs, vol. 18, no. 8, pp. 1197–1218, 2009. View at Publisher · View at Google Scholar · View at Scopus
  154. G. P. Stathopoulos, D. Antoniou, J. Dimitroulis, J. Stathopoulos, K. Marosis, and P. Michalopoulou, “Comparison of liposomal cisplatin versus cisplatin in non-squamous cell non-small-cell lung cancer,” Cancer Chemotherapy and Pharmacology, vol. 68, no. 4, pp. 945–950, 2011. View at Publisher · View at Google Scholar
  155. N. J. Wheate and J. G. Collins, “Multi-nuclear platinum complexes as anti-cancer drugs,” Coordination Chemistry Reviews, vol. 241, no. 1-2, pp. 133–145, 2003. View at Publisher · View at Google Scholar · View at Scopus
  156. N. J. Wheate and J. G. Collins, “Multi-nuclear platinum drugs: a new paradigm in chemotherapy,” Current Medicinal Chemistry—Anti-Cancer Agents, vol. 5, no. 3, pp. 267–279, 2005. View at Publisher · View at Google Scholar · View at Scopus
  157. J. B. Mangrum and N. P. Farrell, “Excursions in polynuclear platinum DNA binding,” Chemical Communications, vol. 46, no. 36, pp. 6640–6650, 2010. View at Publisher · View at Google Scholar · View at Scopus
  158. R. A. Ruhayel, J. S. Langner, M. J. Oke, S. J. Berners-Price, I. Zgani, and N. P. Farrell, “Chimeric platinum-polyamines and DNA binding. Kinetics of DNA interstrand cross-link formation by dinuclear platinum complexes with polyamine linkers,” Journal of the American Chemical Society, vol. 134, no. 16, pp. 7135–7146, 2012. View at Publisher · View at Google Scholar
  159. Y. Qu, N. J. Scarsdale, M. C. Tran, and N. P. Farrell, “Cooperative effects in long-range 1,4 DNA-DNA interstrand cross-links formed by polynuclear platinum complexes: an unexpected syn orientation of adenine bases outside the binding sites,” Journal of Biological Inorganic Chemistry, vol. 8, no. 1-2, pp. 19–28, 2003. View at Publisher · View at Google Scholar · View at Scopus
  160. K. Chvalova, J. Kasparkova, N. Farrell, and V. Brabec, “Deoxyribonuclease I footprinting reveals different DNA binding modes of bifunctional platinum complexes,” The FEBS Journal, vol. 273, no. 15, pp. 3467–3478, 2006. View at Publisher · View at Google Scholar · View at Scopus
  161. E. Monti, M. Gariboldi, A. Maiocchi et al., “Cytotoxicity of cis-platinum(II) conjugate models. The effect of chelating arms and leaving groups on cytotoxicity: a quantitative structure-activity relationship approach,” Journal of Medicinal Chemistry, vol. 48, no. 3, pp. 857–866, 2005. View at Publisher · View at Google Scholar · View at Scopus
  162. M. R. Costa Couri, M. Vieira de Almeida, A. P. Soares Fontes et al., “Synthesis of polyamines from ethylenediamine and their platinum(II) complexes, potential antitumor agents,” European Journal of Inorganic Chemistry, no. 9, pp. 1868–1874, 2006. View at Publisher · View at Google Scholar · View at Scopus
  163. Q. Liu, Y. Qu, R. van Antwerpen, and N. Farrell, “Mechanism of the membrane interaction of polynuclear platinum anticancer agents. Implications for cellular uptake,” Biochemistry, vol. 45, no. 13, pp. 4248–4256, 2006. View at Publisher · View at Google Scholar · View at Scopus
  164. J. W. Williams, Y. Qu, G. H. Bulluss, E. Alvorado, and N. P. Farrell, “Dinuclear platinum complexes with biological relevance based on the 1,2-diaminocyclohexane carrier ligand,” Inorganic Chemistry, vol. 46, no. 15, pp. 5820–5822, 2007. View at Publisher · View at Google Scholar · View at Scopus
  165. S. M. Fiuza, A. M. Amado, P. J. Oliveira, V. A. Sardão, L. A. E. Batista de Carvalho, and M. P. M. Marques, “Pt(II) vs Pd(II) polyamine complexes as new anticancer drugs: a structure-activity study,” Letters in Drug Design and Discovery, vol. 3, no. 3, pp. 149–151, 2006. View at Publisher · View at Google Scholar · View at Scopus
  166. L. J. Teixeira, M. Seabra, E. Reis et al., “Cytotoxic activity of metal complexes of biogenic polyamines: polynuclear platinum(II) chelates,” Journal of Medicinal Chemistry, vol. 47, no. 11, pp. 2917–2925, 2004. View at Publisher · View at Google Scholar · View at Scopus
  167. M. P. M. Marques, T. Girão, M. C. Pedroso de Lima, A. Gameiro, E. Pereira, and P. Garcia, “Cytotoxic effects of metal complexes of biogenic polyamines. I. Platinum(II) spermidine compounds: prediction of their antitumour activity,” Biochimica et Biophysica Acta—Molecular Cell Research, vol. 1589, no. 1, pp. 63–70, 2002. View at Publisher · View at Google Scholar · View at Scopus
  168. A. S. Soares, S. M. Fiuza, M. J. Gonçalves, L. A. E. Batista de Carvalho, M. P. M. Marques, and A. M. Urbano, “Effect of the metal center on the antitumor activity of the analogous dinuclear spermine chelates (PdCl2)(2)(Spermine) and (PtCl2)(2)(Spermine),” Letters in Drug Design and Discovery, vol. 4, no. 7, pp. 460–463, 2007. View at Publisher · View at Google Scholar · View at Scopus
  169. C. Navarro-Ranninger, F. Zamora, J. M. Perez et al., “Palladium(II) salt and complexes of spermidine with a six-member chelate ring. Synthesis, characterization, and initial DNA-binding and antitumor studies,” Journal of Inorganic Biochemistry, vol. 46, no. 4, pp. 267–279, 1992. View at Publisher · View at Google Scholar · View at Scopus
  170. C. Navarro-Ranninger, J. M. Perez, F. Zamora, V. M. Gonzalez, J. R. Masaguer, and C. Alonso, “Palladium(II) compounds of putrescine and spermine. Synthesis, characterization, and DNA-binding and antitumor properties,” Journal of Inorganic Biochemistry, vol. 52, no. 1, pp. 37–49, 1993. View at Publisher · View at Google Scholar · View at Scopus
  171. C. Navarro-Ranninger, P. Amo Ochoa, J. R. Masaguer, J. M. Pérez, V. M. González, and C. Alonso, “Platinum (II) and (IV) spermidine complexes. Synthesis, characterization, and biological studies,” Journal of Inorganic Biochemistry, vol. 53, no. 3, pp. 177–190, 1994. View at Publisher · View at Google Scholar · View at Scopus
  172. M. Navarro, N. P. Peña, I. Colmenares, T. González, M. Arsenak, and P. Taylor, “Synthesis and characterization of new palladium-clotrimazole and palladium-chloroquine complexes showing cytotoxicity for tumor cell lines in vitro,” Journal of Inorganic Biochemistry, vol. 100, no. 1, pp. 152–157, 2006. View at Publisher · View at Google Scholar · View at Scopus
  173. A. Hegmans, J. Kasparkova, O. Vrana, L. R. Kelland, V. Brabec, and N. P. Farrell, “Amide-based prodrugs of spermidine-bridged dinuclear platinum. Synthesis, DNA binding, and biological activity,” Journal of Medicinal Chemistry, vol. 51, no. 7, pp. 2254–2260, 2008. View at Publisher · View at Google Scholar · View at Scopus
  174. S. M. Fiuza, A. M. Amado, H. F. dos Santos, M. P. M. Marques, and L. A. E. Batista de Carvalho, “Conformational and vibrational study of cis-diamminedichloropalladium(ii),” Physical Chemistry Chemical Physics, vol. 12, no. 42, pp. 14309–14321, 2010. View at Publisher · View at Google Scholar · View at Scopus
  175. R. Tummala, P. Diegelman, S. M. Fiuza et al., “Characterization of Pt-, Pd-spermine complexes for their effect on polyamine pathway and cisplatin resistance in A2780 ovarian carcinoma cells,” Oncology Reports, vol. 24, no. 1, pp. 15–24, 2010. View at Publisher · View at Google Scholar · View at Scopus
  176. R. Tummala, P. Diegelman, S. Hector et al., “Combination effects of platinum drugs and N1, N11 diethylnorspermine on spermidine/spermine N1-acetyltransferase, polyamines and growth inhibition in A2780 human ovarian carcinoma cells and their oxaliplatin and cisplatin-resistant variants,” Cancer Chemotherapy and Pharmacology, vol. 67, no. 2, pp. 401–414, 2011. View at Publisher · View at Google Scholar · View at Scopus
  177. A. Tassoni, N. Bagni, M. Ferri et al., “Helianthus tuberosus and polyamine research: past and recent applications of a classical growth model,” Plant Physiology and Biochemistry, vol. 48, no. 7, pp. 496–505, 2010. View at Google Scholar · View at Scopus
  178. O. Corduneanu, A. M. Chiorcea-Paquim, S. M. Fiuza, M. P. M. Marques, and A. M. Oliveira-Brett, “Polynuclear palladium complexes with biogenic polyamines: AFM and voltammetric characterization,” Bioelectrochemistry, vol. 78, no. 2, pp. 97–105, 2010. View at Publisher · View at Google Scholar · View at Scopus
  179. O. Corduneanu, A. M. Chiorcea-Paquim, V. Diculescu, S. M. Fiuza, M. P. M. Marques, and A. M. Oliveira-Brett, “DNA interaction with palladium chelates of biogenic polyamines using atomic force microscopy and voltammetric characterization,” Analytical Chemistry, vol. 82, no. 4, pp. 1245–1252, 2010. View at Publisher · View at Google Scholar · View at Scopus
  180. S. M. Fiuza, J. Holy, L. A. E. Batista de Carvalho, and M. P. M. Marques, “Biologic activity of a dinuclear Pd(II)-spermine complex toward human breast cancer,” Chemical Biology and Drug Design, vol. 77, no. 6, pp. 477–488, 2011. View at Publisher · View at Google Scholar · View at Scopus
  181. A. L. M. Batista de Carvalho, S. M. Fiuza, J. Tomkinson, L. A. E. Batista de Carvalho, and M. P. M. Marques, “Pt(II) complexes with linear diamines-part i: vibrational study of Pt-diaminopropane,” International Journal of Spectroscopy, vol. 27, no. 5-6, pp. 403–413, 2012. View at Publisher · View at Google Scholar
  182. E. Escribano, M. Font-Bardia, T. Calvet, J. Lorenzo, P. Gamez, and V. Moreno, “DNA binding studies of a series of cis-[Pt(Am)2X2] complexes (Am = inert amine, X = labile carboxylato ligand),” Inorganica Chimica Acta, vol. 394, pp. 65–76, 2013. View at Publisher · View at Google Scholar
  183. U. Bierbach, T. W. Hambley, and N. Farrell, “Modification of platinum(II) antitumor complexes with sulfur ligands. 1. Synthesis, structure, and spectroscopic properties of cationic complexes of the types [PtCl(diamine) (L)]NO3 and [{PtCl(diamine)}2(L-L)](NO3)2 (L = monofunctional thiourea derivative; L-L = bifunctional thiourea derivative),” Inorganic Chemistry, vol. 37, no. 4, pp. 708–716, 1998. View at Google Scholar · View at Scopus
  184. L. Gatti, P. Perego, R. Leone et al., “Novel bis-platinum complexes endowed with an improved pharmacological profile,” Molecular Pharmaceutics, vol. 7, no. 1, pp. 207–216, 2010. View at Publisher · View at Google Scholar · View at Scopus
  185. P. Perego, C. Caserini, L. Gatti et al., “A novel trinuclear platinum complex overcomes cisplatin resistance an osteosarcoma cell system,” Molecular Pharmacology, vol. 55, no. 3, pp. 528–534, 1999. View at Google Scholar · View at Scopus
  186. S. Komeda, T. Moulaei, K. K. Woods, M. Chikuma, N. P. Farrell, and L. D. Williams, “A third mode of DNA binding: phosphate clamps by a polynuclear platinum complex,” Journal of the American Chemical Society, vol. 128, no. 50, pp. 16092–16103, 2006. View at Publisher · View at Google Scholar · View at Scopus
  187. Y. Qu, A. Harris, A. Hegmans et al., “Synthesis and DNA conformational changes of non-covalent polynuclear platinum complexes,” Journal of Inorganic Biochemistry, vol. 98, no. 10, pp. 1591–1598, 2004. View at Publisher · View at Google Scholar · View at Scopus
  188. A. Harris, Y. Qu, and N. Farrell, “Unique cooperative binding interaction observed between a minor groove binding Pt antitumor agent and hoeschst dye 33258,” Inorganic Chemistry, vol. 44, no. 5, pp. 1196–1198, 2005. View at Publisher · View at Google Scholar · View at Scopus
  189. A. L. Harris, X. Yang, A. Hegmans et al., “Synthesis, characterization, and cytotoxicity of a novel highly charged trinuclear platinum compound. Enhancement of cellular uptake with charge,” Inorganic Chemistry, vol. 44, no. 26, pp. 9598–9600, 2005. View at Publisher · View at Google Scholar · View at Scopus
  190. G. Pratesi, P. Perego, D. Polizzi et al., “A novel charged trinuclear platinum complex effective against cisplatin-resistant tumours: hypersensitivity of p53-mutant human tumour xenografts,” British Journal of Cancer, vol. 80, no. 12, pp. 1912–1919, 1999. View at Publisher · View at Google Scholar · View at Scopus
  191. T. D. McGregor, A. Hegmans, J. Kasparkova et al., “A comparison of DNA binding profiles of dinuclear platinum compounds with polyamine linkers and the trinuclear platinum phase II clinical agent BBR3464,” Journal of Biological Inorganic Chemistry, vol. 7, no. 4-5, pp. 397–404, 2002. View at Publisher · View at Google Scholar · View at Scopus
  192. Y. Qu and N. Farrell, “Effect of diamine linker on the chemistry of bis(platinum) complexes. A comparison of the aqueous solution behavior of 1,4-butanediamine and 2,5-dimethyl-2,5-hexanediamine complexes,” Journal of Inorganic Biochemistry, vol. 40, no. 3, pp. 255–264, 1990. View at Publisher · View at Google Scholar · View at Scopus
  193. N. Farrell, Y. Qu, J. Kasparkova et al., “Chemical studies and DNA binding of charged polynuclear platinum complexes,” Proceedings of the American Association for Cancer Research, vol. 38, pp. 310–315, 1997. View at Google Scholar
  194. Y. Qu, H. Rauter, A. P. S. Fontes, R. Bandarage, L. R. Kelland, and N. Farrell, “Synthesis, characterization, and cytotoxicity of trifunctional dinuclear platinum complexes: comparison of effects of geometry and polyfunctionality on biological activity,” Journal of Medicinal Chemistry, vol. 43, no. 16, pp. 3189–3192, 2000. View at Publisher · View at Google Scholar · View at Scopus
  195. U. Bierbach and N. Farrell, “Modulation of nucleotide binding of trans platinum(II) complexes by planar ligands. A combined proton NMR and molecular mechanics study,” Inorganic Chemistry, vol. 36, no. 17, pp. 3657–3665, 1997. View at Google Scholar · View at Scopus
  196. N. Farrell, “DNA-binding and chemistry of dinuclear platinum complexes,” Comments on Inorganic Chemistry, vol. 16, no. 6, pp. 373–389, 1995. View at Publisher · View at Google Scholar
  197. N. Farrell, “Current status of structure-activity relationships of platinum anticancer drugs: activation of the trans geometry,” Metal Ions in Biological Systems, vol. 32, pp. 603–639, 1996. View at Google Scholar · View at Scopus
  198. C. Hofr, N. Farrell, and V. Brabec, “Thermodynamic properties of duplex DNA containing a site-specific d(GpG) intrastrand crosslink formed by an antitumor dinuclear platinum complex,” Nucleic Acids Research, vol. 29, no. 10, pp. 2034–2040, 2001. View at Google Scholar · View at Scopus
  199. J. Zehnulova, J. Kasparkova, N. Farrell, and V. Brabec, “Conformation, recognition by high mobility group domain proteins, and nucleotide excision repair of DNA intrastrand cross-links of novel antitumor trinuclear platinum complex BBR3464,” The Journal of Biological Chemistry, vol. 276, no. 25, pp. 22191–22199, 2001. View at Publisher · View at Google Scholar · View at Scopus
  200. A. Hegmans, Y. Qu, L. R. Kelland, J. D. Roberts, and N. Farrell, “Novel approaches to polynuclear platinum pro-drugs. Selective release of cytotoxic platinum-spermidine species through hydrolytic cleavage of carbamates,” Inorganic Chemistry, vol. 40, no. 24, pp. 6108–6114, 2001. View at Publisher · View at Google Scholar · View at Scopus
  201. J. Kasparkova, J. Zehnulova, N. Farrell, and V. Brabec, “DNA interstrand cross-links of the novel antitumor trinuclear platinum complex BBR3464. Conformation, recognition by high mobility group domain proteins, and nucleotide excision repair,” The Journal of Biological Chemistry, vol. 277, no. 50, pp. 48076–48086, 2002. View at Publisher · View at Google Scholar · View at Scopus
  202. J. Kasparkova, M. Fojta, N. Farrell, and V. Brabec, “Differential recognition by the tumor suppressor protein p53 of DNA modified by the novel antitumor trinuclear platinum drug BBR3464 and cisplatin,” Nucleic Acids Research, vol. 32, no. 18, pp. 5546–5552, 2004. View at Publisher · View at Google Scholar · View at Scopus
  203. C. Billecke, S. Finniss, L. Tahash et al., “Polynuclear platinum anticancer drugs are more potent than cisplatin and induce cell cycle arrest in glioma,” Neuro-Oncology, vol. 8, no. 3, pp. 215–226, 2006. View at Publisher · View at Google Scholar · View at Scopus
  204. J. Zhang, L. Wang, Z. Xing et al., “Status of Bi- and multi-nuclear platinum anticancer drug development,” Anti-Cancer Agents in Medicinal Chemistry, vol. 10, no. 4, pp. 272–282, 2010. View at Google Scholar · View at Scopus
  205. T. Muchova, S. M. Quintal, N. P. Farrell, V. Brabec, and J. Kasparkova, “Antitumor bifunctional dinuclear Pt(II) complex BBR 3535 forms interduplex DNA cross-links under molecular crowding conditions,” Journal of Biological Inorganic Chemistry, vol. 17, no. 2, pp. 239–245, 2012. View at Publisher · View at Google Scholar
  206. P. Perego, L. Gatti, C. Caserini et al., “The cellular basis of the efficacy of the trinuclear platinum complex BBR 3464 against cisplatin-resistant cells,” Journal of Inorganic Biochemistry, vol. 77, no. 1-2, pp. 59–64, 1999. View at Publisher · View at Google Scholar · View at Scopus
  207. M. B. G. Kloster, J. C. Hannis, D. C. Muddiman, and N. Farrell, “Consequences of nucleic acid conformation on the binding of a trinuclear platinum drug,” Biochemistry, vol. 38, no. 45, pp. 14731–14737, 1999. View at Publisher · View at Google Scholar · View at Scopus
  208. J. Kasparkova, O. Vrana, N. Farrell, and V. Brabec, “Effect of the geometry of the central coordination sphere in antitumor trinuclear platinum complexes on DNA binding,” Journal of Inorganic Biochemistry, vol. 98, no. 10, pp. 1560–1569, 2004. View at Publisher · View at Google Scholar · View at Scopus
  209. P. Kabolizadeh, J. Ryan, and N. Farrell, “Differences in the cellular response and signaling pathways of cisplatin and BBR3464 ([{trans-PtCl(NH3)2}2μ-(trans-Pt(NH3)2(H2N(CH2)6-NH2)2)]4+) influenced by copper homeostasis,” Biochemical Pharmacology, vol. 73, no. 9, pp. 1270–1279, 2007. View at Publisher · View at Google Scholar · View at Scopus
  210. Y. Qu, M. C. Tran, and N. P. Farrell, “Structural consequences of a 33 DNA interstrand cross-link by a trinuclear platinum complex: unique formation of two such cross-links in a 10-mer duplex,” Journal of Biological Inorganic Chemistry, vol. 14, no. 6, pp. 969–977, 2009. View at Publisher · View at Google Scholar · View at Scopus
  211. J. Malina, N. P. Farrell, and V. Brabec, “DNA interstrand cross-links of an antitumor trinuclear platinum(II) complex: thermodynamic analysis and chemical probing,” Chemistry, vol. 6, no. 6, pp. 1566–1574, 2011. View at Publisher · View at Google Scholar · View at Scopus
  212. J. Kjellstrom, S. M. Oredsson, and J. Wennerberg, “Increased toxicity of a trinuclear Pt-compound in a human squamous carcinoma cell line by polyamine depletion,” Cancer Cell International, vol. 12, no. 20, pp. 1–9, 2012. View at Google Scholar
  213. D. I. Jodrell, T. R. J. Evans, W. Steward et al., “Phase II studies of BBR3464, a novel tri-nuclear platinum complex, in patients with gastric or gastro-oesophageal adenocarcinoma,” European Journal of Cancer, vol. 40, no. 12, pp. 1872–1877, 2004. View at Publisher · View at Google Scholar · View at Scopus
  214. E. I. Montero, B. T. Benedetti, J. B. Mangrum, M. J. Oehlsen, Y. Qu, and N. P. Farrell, “Pre-association of polynuclear platinum anticancer agents on a protein, human serum albumin. Implications for drug design,” Dalton Transactions, no. 43, pp. 4938–4942, 2007. View at Publisher · View at Google Scholar · View at Scopus
  215. B. T. Benedetti, E. J. Peterson, P. Kabolizadeh, A. Martínez, R. Kipping, and N. P. Farrell, “Effects of noncovalent platinum drug-protein interactions on drug efficacy: use of fluorescent conjugates as probes for drug metabolism,” Molecular Pharmaceutics, vol. 8, no. 3, pp. 940–948, 2011. View at Publisher · View at Google Scholar · View at Scopus
  216. H. Silva, F. Frezard, E. J. Peterson, P. Kabolizadeh, J. J. Ryan, and N. P. Farrell, “Heparan sulfate proteoglycan-mediated entry pathway for charged tri-platinum compounds: differential cellular accumulation mechanisms for platinum,” Molecular Pharmaceutics, vol. 9, no. 6, pp. 1795–1802, 2012. View at Publisher · View at Google Scholar
  217. H. Cheng, F. Huq, P. Beale, and K. Fisher, “Synthesis and activity of a trinuclear platinum complex: [{trans-PtCl(NH3)2}2mu-{trans-Pt(3-hydroxypyridine)2(H2N(CH2)6NH2)2}]Cl4 in ovarian cancer cell lines,” European Journal of Medicinal Chemistry, vol. 40, no. 8, pp. 772–781, 2005. View at Publisher · View at Google Scholar · View at Scopus
  218. A. L. Harris, J. J. Ryan, and N. Farrell, “Biological consequences of trinuclear platinum complexes: comparison of [{trans-PtCl(NH3)2}2μ-(trans-Pt(NH3)2(H2N(CH2)6-NH2)2)]4+ (BBR 3464) with its noncovalent congeners,” Molecular Pharmacology, vol. 69, no. 2, pp. 666–672, 2006. View at Publisher · View at Google Scholar · View at Scopus
  219. H. Tayyem, F. Huq, J. Q. Yu, P. Beale, and K. Fisher, “Synthesis and activity of a trinuclear platinum complex: [{trans-PtCl(NH3)2}2μ-{trans-Pt(3-hydroxypyridine)2(H2N(CH2)6NH2)2}]Cl4 in ovarian cancer cell lines,” ChemMedChem, vol. 3, no. 1, pp. 145–151, 2008. View at Publisher · View at Google Scholar · View at Scopus
  220. J. Malina, J. Kasparkova, N. P. Farrell, and V. Brabec, “Walking of antitumor bifunctional trinuclear PtII complex on double-helical DNA,” Nucleic Acids Research, vol. 39, no. 2, pp. 720–728, 2011. View at Publisher · View at Google Scholar · View at Scopus
  221. G. Pratesi, L. Dal Bo, A. Paolicchi, P. Tonarelli, R. Tongiani, and F. Zunino, “The role of the glutathione-dependent system in tumor sensitivity to cisplatin: a study of human tumor xenografts,” Annals of Oncology, vol. 6, no. 3, pp. 283–289, 1995. View at Google Scholar · View at Scopus
  222. H. H. W. Chen and M. T. Kuo, “Role of glutathione in the regulation of cisplatin resistance in cancer chemotherapy,” Metal-Based Drugs, vol. 2010, Article ID 430939, 2010. View at Publisher · View at Google Scholar · View at Scopus
  223. S. M. Quintal, Q. A. Depaula, and N. P. Farrell, “Zinc finger proteins as templates for metal ion exchange and ligand reactivity. Chemical and biological consequences,” Metallomics, vol. 3, no. 2, pp. 121–139, 2011. View at Publisher · View at Google Scholar · View at Scopus
  224. Q. A. Depaula, S. D. Tsotsoros, Y. Qu, C. A. Bayse, and N. P. Farrell, “Platinum-nucleobase Ptn4 complexes as chemotypes for selective pePtide reactions with biomolecules,” Inorganica Chimica Acta, vol. 393, pp. 222–229, 2012. View at Publisher · View at Google Scholar
  225. G. B. Deacon, Platinum and Other Metal Coordination Compound in Cancer Cemotherapy, Plenum, New York, NY, USA, 1991.
  226. Q. Zhang, W. Zhong, B. Xing, W. Tang, and Y. Chen, “Binding properties and stoichiometries of a palladium(II) complex to metallothioneins in vivo and in vitro,” Journal of Inorganic Biochemistry, vol. 72, no. 3-4, pp. 195–200, 1998. View at Publisher · View at Google Scholar · View at Scopus
  227. P. A. Andrews, M. P. Murphy, and S. B. Howell, “Differential potentiation of alkylating and platinating agent cytotoxicity in human ovarian carcinoma cells by glutathione depletion,” Cancer Research, vol. 45, no. 12, part 1, pp. 6250–6253, 1985. View at Google Scholar · View at Scopus
  228. J. K. Lau and D. V. Deubel, “Loss of amine from platinum(II) complexes: implications for cisplatin inactivation, storage, and resistance,” Chemistry, vol. 11, no. 9, pp. 2849–2855, 2005. View at Google Scholar · View at Scopus
  229. X. Wang and Z. Guo, “The role of sulfur in platinum anticancer chemotherapy,” Anti-Cancer Agents in Medicinal Chemistry, vol. 7, no. 1, pp. 19–34, 2007. View at Publisher · View at Google Scholar · View at Scopus
  230. J. Reedijk, “Why does cisplatin reach guanine-N7 with competing S-donor ligands available in the cell?” Chemical Reviews, vol. 99, no. 9, pp. 2499–2510, 1999. View at Google Scholar · View at Scopus
  231. L. Giovagnini, L. Ronconi, D. Aldinucci, D. Lorenzon, S. Sitran, and D. Fregona, “Synthesis, characterization, and comparative in vitro cytotoxicity studies of platinum(II), palladium(II), and gold(III) methylsarcosinedithiocarbamate complexes,” Journal of Medicinal Chemistry, vol. 48, no. 5, pp. 1588–1595, 2005. View at Publisher · View at Google Scholar · View at Scopus
  232. S. van Zutphen, M. Kraus, C. Driessen, G. A. van der Marel, H. S. Overkleeft, and J. Reedijk, “Probing the potential of platinum(II) complexes for the inhibition of thiol-dependent enzymatic activity,” Journal of Inorganic Biochemistry, vol. 99, no. 6, pp. 1384–1389, 2005. View at Publisher · View at Google Scholar · View at Scopus
  233. P. Umapathy, “The chemical and biochemical consequences of the binding of the antitumour drug cisplatin and other platinum group metal complexes to DNA,” Coordination Chemistry Reviews, vol. 95, no. 2, pp. 129–181, 1989. View at Google Scholar · View at Scopus
  234. T. A. K. Al-Allaf and L. J. Rashan, “Cis- and trans- platinum and palladium complexes: a comparative study review as antitumour agents,” Bollettino Chimico Farmaceutico, vol. 140, no. 3, pp. 205–210, 2001. View at Google Scholar · View at Scopus
  235. F. Huq, H. Tayyem, A. Abdullah, P. Beale, and K. Fisher, “Synthesis and characterization and binding of amine-palladium(II) complexes and their interaction with DNA,” Asian Journal of Chemistry, vol. 18, no. 1, pp. 65–78, 2006. View at Google Scholar · View at Scopus
  236. S. Ray, R. Mohan, J. K. Singh et al., “Anticancer and antimicrobial metallopharmaceutical agents based on palladium, gold, and silver N-heterocyclic carbene complexes,” Journal of the American Chemical Society, vol. 129, no. 48, pp. 15042–15053, 2007. View at Publisher · View at Google Scholar · View at Scopus
  237. A. Garoufis, S. K. Hadjikakou, and N. Hadjiliadis, “Palladium coordination compounds as anti-viral, anti-fungal, anti-microbial and anti-tumor agents,” Coordination Chemistry Reviews, vol. 253, no. 9-10, pp. 1384–1397, 2009. View at Publisher · View at Google Scholar · View at Scopus
  238. E. Gao, C. Liu, M. Zhu, H. Lin, Q. Wu, and L. Liu, “Current development of pd(II) complexes as potential antitumor agents,” Anti-Cancer Agents in Medicinal Chemistry, vol. 9, no. 3, pp. 356–368, 2009. View at Google Scholar · View at Scopus
  239. A. Chevry, M. L. Teyssot, A. Maisonial et al., “Click chelators—the behavior of platinum and palladium complexes in the presence of guanosine and DNA,” European Journal of Inorganic Chemistry, no. 22, pp. 3513–3519, 2010. View at Publisher · View at Google Scholar · View at Scopus
  240. J. L. Butour, S. Wimmer, F. Wimmer, and P. Castan, “Palladium(II) compounds with potential antitumour properties and their platinum analogues: a comparative study of the reaction of some erotic acid derivatives with DNA in vitro,” Chemico-Biological Interactions, vol. 104, no. 2-3, pp. 165–178, 1997. View at Publisher · View at Google Scholar · View at Scopus
  241. P. Banerjee, “Interaction of nitrogen bases with some platinum(ii) and palladium(ii) complexes-usual and unusual features,” Coordination Chemistry Reviews, vol. 190–192, pp. 19–28, 1999. View at Publisher · View at Google Scholar
  242. H. Mansuri-Torshizi, S. Ghadimy, and N. Akbarzadeh, “Synthesis, characterization, DNA binding and cytotoxic studies of platinum(II) and palladium(II) complexes of the 2,2-bipyridine and an anion of 1,1-cyclobutanedicarboxylic acid,” Chemical and Pharmaceutical Bulletin, vol. 49, no. 12, pp. 1517–1520, 2001. View at Publisher · View at Google Scholar · View at Scopus
  243. E. Budzisz, U. Krajewska, and M. Rózalski, “Cytotoxic and proapoptotic effects of new Pd(II) and Pt(II)-complexes with 2-ethanimidoyl-2-methoxy-2H-1,2-benzoxaphosphinin-4-ol-2-oxide,” Polish Journal of Pharmacology, vol. 56, no. 4, pp. 473–478, 2004. View at Google Scholar · View at Scopus
  244. F. L. Wimmer, S. Wimmer, P. Castan, S. Cros, N. Johnson, and E. Colacio-Rodrigez, “The antitumor activity of some palladium(II) complexes with chelating ligands,” Anticancer Research, vol. 9, no. 3, pp. 791–793, 1989. View at Google Scholar · View at Scopus
  245. M. R. Shehata, “Mixed ligand complexes of diaquo (2,2-bipyridine)palladium(II) with cyclobutane-1,1-dicarboxylic acid and DNA constituents,” Transition Metal Chemistry, vol. 26, no. 1-2, pp. 198–204, 2001. View at Publisher · View at Google Scholar · View at Scopus
  246. J. Kuduk-Jaworska, A. Puszko, M. Kubiak, and M. Pelczyńska, “Synthesis, structural, physico-chemical and biological properties of new palladium(II) complexes with 2,6-dimethyl-4-nitropyridine,” Journal of Inorganic Biochemistry, vol. 98, no. 8, pp. 1447–1456, 2004. View at Publisher · View at Google Scholar · View at Scopus
  247. A. C. F. Caires, “Recent advances involving palladium (II) complexes for the cancer therapy,” Anti-Cancer Agents in Medicinal Chemistry, vol. 7, no. 5, pp. 484–491, 2007. View at Google Scholar · View at Scopus
  248. J. Zhang, F. Zhang, H. Li et al., “Recent progress and future potential for metal complexes as anticancer drugs targeting g-quadruplex DNA,” Current Medicinal Chemistry, vol. 19, no. 18, pp. 2957–2975, 2012. View at Publisher · View at Google Scholar
  249. R. T. Dorr, “A review of the modulation of cisplatin toxicities by chemoprotectants, platinum and other metal coordination compounds in cancer chemotherapy,” in PlatInum and Other Metal CoordInation Compounds in Cancer Chemotherapy, vol. 2, pp. 131–154, Plenum Press, New York, NY, USA, 1996. View at Google Scholar
  250. J. Bünger, J. Stork, and K. Stalder, “Cyto- and genotoxic effects of coordination complexes of platinum, palladium and rhodium in vitro,” International Archives of Occupational and Environmental Health, vol. 69, no. 1, pp. 33–38, 1996. View at Publisher · View at Google Scholar · View at Scopus
  251. M. Zeizinger, J. V. Burda, J. Šponer, V. Kapsa, and J. Leszczynski, “A systematic ab initio study of the hydration of selected palladium square-planar complexes. A comparison with platinum analogues,” The Journal of Physical Chemistry A, vol. 105, no. 34, pp. 8086–8092, 2001. View at Publisher · View at Google Scholar · View at Scopus
  252. C. Bazzicalupi, A. Bencini, A. Bianchi, C. Giorgi, and B. Valtancoli, “Pd(II) complexes of aliphatic polyamine ligands in aqueous solution: thermodynamic and structural features,” Coordination Chemistry Reviews, vol. 184, no. 1, pp. 243–270, 1999. View at Google Scholar · View at Scopus
  253. F. Huq, H. Daghriri, J. Q. Yu, H. Tayyem, P. Beale, and M. Zhang, “Synthesis, characterisation, activities, cell uptake and DNA binding of [{trans-PtCl(NH3)2} {μ-(H2N(CH2)6NH2)} {trans-PdCl(NH3)2](NO3)Cl,” European Journal of Medicinal Chemistry, vol. 39, no. 11, pp. 947–958, 2004. View at Publisher · View at Google Scholar · View at Scopus
  254. H. Daghriri, F. Huq, and P. Beale, “Studies on activities, cell up take and DNA binding of four multinuclear complexes of the form: [{trans-PtCl(NH3)2}2μ-{trans-Pd(NH3)2-(H2N(CH2)nNH2)2}]Cl4 where n=47,” Journal of Inorganic Biochemistry, vol. 98, no. 11, pp. 1722–1733, 2004. View at Publisher · View at Google Scholar · View at Scopus
  255. H. Cheng, F. Huq, P. Beale, and K. Fisher, “Synthesis, characterisation, activities, cell uptake and DNA binding of a trinuclear complex: [{trans-PtCl(NH3)}2μ-{trans-Pd(NH3)(2-hydroxypyridine)-(H2N(CH2)6NH2)2]Cl4,” European Journal of Medicinal Chemistry, vol. 41, no. 7, pp. 896–903, 2006. View at Publisher · View at Google Scholar · View at Scopus
  256. T. Rau, R. Alsfasser, A. Zahl, and R. van Eldik, “Structural and kinetic studies on the formation of platinum(II) and palladium(II) complexes with L-cysteine-derived ligands,” Inorganic Chemistry, vol. 37, no. 17, pp. 4223–4230, 1998. View at Google Scholar · View at Scopus
  257. E. Holló-Sitkei, G. Tárkányi, L. Párkányi, T. Megyes, and G. Besenyei, “Steric effects in the self-assembly of palladium complexes with chelating diamine ligands,” European Journal of Inorganic Chemistry, no. 10, pp. 1573–1583, 2008. View at Publisher · View at Google Scholar · View at Scopus
  258. G. Codina, A. Caubet, C. López, V. Moreno, and E. Molins, “Palladium(ii) and platinum(ii) polyamine complexes: X-ray crystal structures of (sp-4-2)-chloro{N-[(3-amino-κN)propyl]propane-1, 3-diamine-κN,κN}palladium(1+) tetrachloropalladate (2-) (2 : 1) and (r, s)-tetrachloro[μ-(spermine)]dipalladium(ii) (={μ-{N,N-bis[(3-amino-κN)propyl]butane-1, 4-diamine-κN,κN}}tetrachlorodipalladium),” Helvetica Chimica Acta, vol. 82, pp. 1025–1037, 1999. View at Publisher · View at Google Scholar
  259. P. Amo-Ochoa, V. M. González, J. M. Pérez, J. R. Masaguer, C. Alonso, and C. Navarro-Ranninger, “Cytotoxicity, DNA binding, and reactivity against nucleosides of platinum (II) and (IV) spermine compounds,” Journal of Inorganic Biochemistry, vol. 64, no. 4, pp. 287–299, 1996. View at Publisher · View at Google Scholar · View at Scopus
  260. A. M. Amado, S. M. Fiuza, M. P. M. Marques, and L. A. E. Batista de Carvalho, “Conformational and vibrational study of platinum(II) anticancer drugs: cis-diamminedichloroplatinum (II) as a case study,” Journal of Chemical Physics, vol. 127, no. 18, Article ID 185104, 2007. View at Publisher · View at Google Scholar · View at Scopus
  261. S. M. Fiuza, A. M. Amado, M. P. M. Marques, and L. A. E. Batista de Carvalho, “Use of effective core potential calculations for the conformational and vibrational study of platinum(II) anticancer drugs-cis- diamminedichloroplatinum(II) as a case study,” The Journal of Physical Chemistry A, vol. 112, no. 14, pp. 3253–3259, 2008. View at Publisher · View at Google Scholar · View at Scopus
  262. R. D. Graham and D. R. Williams, “The synthesis and screening for anti-bacterial, -cancer, -fungicidal and -viral activities of some complexes of palladium and nickel,” Journal of Inorganic and Nuclear Chemistry, vol. 41, no. 8, pp. 1245–1249, 1979. View at Google Scholar · View at Scopus
  263. N. Farrell, Transition Metal Complexes as Drugs and Chemotherapeutic Agents, Kluwer Academic Publishers, London, UK, 1989.
  264. A. G. Quiroga, J. M. Pérez, I. López-Solera et al., “Novel tetranuclear orthometalated complexes of Pd(II) and Pt(II) derived from p-isopropylbenzaldehyde thiosemicarbazone with cytotoxic activity in cis-DDP resistant tumor cell lines. Interaction of these complexes with DNA,” Journal of Medicinal Chemistry, vol. 41, no. 9, pp. 1399–1408, 1998. View at Publisher · View at Google Scholar · View at Scopus
  265. A. G. Quiroga, J. M. Pérez, E. I. Montero, D. X. West, C. Alonso, and C. Navarro-Ranninger, “Synthesis and characterization of Pd(II) and Pt(II) complexes of p-isopropylbenzaldehyde N-protected thiosemicarbazones. Cytotoxic activity against ras-transformed cells,” Journal of Inorganic Biochemistry, vol. 75, no. 4, pp. 293–301, 1999. View at Publisher · View at Google Scholar · View at Scopus
  266. D. Kovala-Demertzi, A. Domopoulou, M. A. Demertzis, G. Valle, and A. Papageorgiou, “Palladium(II) complexes of 2-acetylpyridine N(4)-methyl, N(4)-ethyl and N(4)-phenyl-thiosemicarbazones. Crystal structure of chloro(2-acetylpyridine N(4)-methylthiosemicarbazonato) palladium(II). Synthesis, spectral studies, in vitro and in vivo antitumour activity,” Journal of Inorganic Biochemistry, vol. 68, no. 2, pp. 147–155, 1997. View at Publisher · View at Google Scholar · View at Scopus
  267. M. A. Ali, A. H. Mirza, R. J. Butcher, and K. A. Crouse, “The preparation, characterization and biological activity of palladium(II) and platinum(II) complexes of tridentate NNS ligands derived from S-methyl- and S-benzyldithiocarbazates and the X-ray crystal structure of the [Pd(mpasme)Cl] complex,” Transition Metal Chemistry, vol. 31, no. 1, pp. 79–87, 2006. View at Publisher · View at Google Scholar · View at Scopus
  268. M. J. Cleare and P. C. Hydes, “Metal complexes as anticancer agents,” in Metal Ions in Biological Systems, pp. 1–62, Marcel Dekker, New York, NY, USA, 1980. View at Google Scholar
  269. J. D. Higgins, L. Neely, and S. Fricker, “Synthesis and cytotoxicity of some cyclometallated palladium complexes,” Journal of Inorganic Biochemistry, vol. 49, no. 2, pp. 149–156, 1993. View at Publisher · View at Google Scholar · View at Scopus
  270. D. Kovala-Demertzi, M. A. Demertzis, J. R. Miller, C. S. Frampton, J. P. Jasinski, and D. X. West, “Structure of bis(2-acetylpyridine 3-hexamethyleneiminylthiosemicarbazonato) palladium(II), a potential antitumor complex,” Journal of Inorganic Biochemistry, vol. 92, no. 2, pp. 137–140, 2002. View at Publisher · View at Google Scholar · View at Scopus
  271. L. Tušek-Božić, I. Matijašić, G. Bocelli et al., “Preparation, characterization and activity of palladium(II) halide complexes with diethyl 2-quinolylmethylphosphonate (2-dqmp). X-ray crystal structures of trans-[Pd(2-dqmp)2X2] (X = Cl or Br),” Journal of the Chemical Society, Dalton Transactions, no. 2, pp. 195–201, 1991. View at Publisher · View at Google Scholar · View at Scopus
  272. C. Mock, I. Puscasu, M. J. Rauterkus, G. Tallen, J. E. A. Wolff, and B. Krebs, “Novel Pt(II) anticancer agents and their Pd(II) analogues: syntheses, crystal structures, reactions with nucleobases and cytotoxicities,” Inorganica Chimica Acta, vol. 319, no. 1-2, pp. 109–116, 2001. View at Publisher · View at Google Scholar · View at Scopus
  273. G. B. Onoa, V. Moreno, M. Font-Bardia, X. Solans, J. M. Pérez, and C. Alonso, “Structural and cytotoxic study of new Pt(II) and Pd(II) complexes with the bi-heterocyclic ligand mepirizole,” Journal of Inorganic Biochemistry, vol. 75, no. 3, pp. 205–212, 1999. View at Publisher · View at Google Scholar · View at Scopus
  274. N. Dodoff, S. Varbanov, G. Borisov, and N. Spassovska, “Platinum (II), platinum (IV), and palladium (II) complexes of amino substituted phosphine oxides: synthesis, characterization, and antitumor activity,” Journal of Inorganic Biochemistry, vol. 39, no. 3, pp. 201–208, 1990. View at Publisher · View at Google Scholar · View at Scopus
  275. M. Z. Wiśniewski and T. Gtowiak, “The structure and properties of a palladium(II) complex of 2-mercapto-1-methylimidazole,” Polish Journal of Chemistry, vol. 72, no. 3, pp. 514–518, 1998. View at Google Scholar · View at Scopus
  276. M. Z. Wiśniewski, J. Wietrzyk, and A. Opolski, “Novel Ru(III), Rh(III), Pd(II) and Pt(II) complexes with ligands incorporating azole and pyrimidine rings. I. Antiproliferative activity in vitro,” Archivum Immunologiae et Therapiae Experimentalis, vol. 48, no. 1, pp. 51–55, 2000. View at Google Scholar · View at Scopus
  277. D. Kovala-Demertzi, M. A. Demertzis, E. Filiou et al., “Platinum(II) and palladium(II) complexes with 2-acetyl pyridine 4N-ethyl thiosemicarbazone able to overcome the cis-platin resistance. Structure, antibacterial activity and DNA strand breakage,” BioMetals, vol. 16, no. 3, pp. 411–418, 2003. View at Publisher · View at Google Scholar · View at Scopus
  278. A. G. Quiroga and C. N. Ranninger, “Contribution to the SAR field of metallated and coordination complexes: studies of the palladium and platinum derivatives with selected thiosemicarbazones as antitumoral drugs,” Coordination Chemistry Reviews, vol. 248, no. 1-2, pp. 119–133, 2004. View at Publisher · View at Google Scholar · View at Scopus
  279. K. Akdi, R. A. Vilaplana, S. Kamah, J. A. R. Navarro, J. M. Salas, and F. González-Vílchez, “Study of the biological effects and DNA damage exerted by a new dipalladium-Hmtpo complex on human cancer cells,” Journal of Inorganic Biochemistry, vol. 90, no. 1-2, pp. 51–60, 2002. View at Publisher · View at Google Scholar · View at Scopus
  280. J. Dupont, C. S. Consorti, and J. Spencer, “The potential of palladacycles: more than just precatalysts,” Chemical Reviews, vol. 105, no. 6, pp. 2527–2571, 2005. View at Publisher · View at Google Scholar · View at Scopus
  281. H. Mansuri-Torshizi, R. Mital, T. S. Srivastava, H. Parekh, and M. P. Chitnis, “Synthesis, characterization, and cytotoxic studies of α-diimine/1,2- diamine platinum(II) and palladium(II) complexes of selenite and tellurite and binding of some of these complexes to DNA,” Journal of Inorganic Biochemistry, vol. 44, no. 4, pp. 239–247, 1991. View at Publisher · View at Google Scholar · View at Scopus
  282. A. S. Abu-Surrah, M. Kettunen, K. Lappalainen, U. Piironen, M. Klinga, and M. Leskelä, “Synthesis of new chiral diimine palladium(II) and nickel(II) complexes bearing oxazoline- and myrtanyl-based nitrogen ligands. Crystal structure of the C2-symmetric complex [{(1R,2S)-inda-box}PdCl2],” Polyhedron, vol. 21, no. 1, pp. 27–31, 2002. View at Publisher · View at Google Scholar · View at Scopus
  283. B. T. Khan, J. Bhatt, K. Najmuddin, S. Shamsuddin, and K. Annapoorna, “Synthesis, antimicrobial, and antitumor activity of a series of palladium(II) mixed ligand complexes,” Journal of Inorganic Biochemistry, vol. 44, no. 1, pp. 55–63, 1991. View at Publisher · View at Google Scholar · View at Scopus
  284. H. Mansuri-Torshizi, T. S. Srivastava, H. K. Parekh, and M. P. Chitnis, “Synthesis, spectroscopic, cytotoxic, and DNA binding studies of binuclear 2,2-bipyridine-platinum(II) and -palladium(II) complexes of meso-α,α-diaminoadipic and meso-α,α-diaminosuberic acids,” Journal of Inorganic Biochemistry, vol. 45, no. 2, pp. 135–148, 1992. View at Publisher · View at Google Scholar · View at Scopus
  285. H. Hohmann and R. van Eldik, “Rate and equilibrium data for substitution reactions of diaqua(ethylenediamine)palladium(II) with chloride in aqueous solution,” Inorganica Chimica Acta, vol. 174, no. 1, pp. 87–92, 1990. View at Google Scholar · View at Scopus
  286. H. Hohmann, S. Suvachittanont, and R. van Eldik, “A kinetic study of the substitution behaviour of aqua and chloro complexes of ethylenediaminepalladium(II) in aqueous solution,” Inorganica Chimica Acta, vol. 177, no. 1, pp. 51–58, 1990. View at Google Scholar · View at Scopus
  287. F. Huq, H. Tayyem, P. Beale, and J. Q. Yu, “Studies on the activity of three palladium(II) compounds of the form: trans-PdL2Cl2 where L = 2-hydroxypyridine, 3-hydroxypyridine, and 4-hydroxypyridine,” Journal of Inorganic Biochemistry, vol. 101, no. 1, pp. 30–35, 2007. View at Publisher · View at Google Scholar · View at Scopus
  288. A. S. Abu-Surrah, T. A. K. Al-Allaf, M. Klinga, and M. Ahlgrend, “Chiral palladium(II) and platinum(II) complexes of diaminocyclohexane: X-ray structures of (1R,2R)-(-)-1,2-diaminocyclohexane dihydrochloride and its corresponding oxalato platinum(II) complex,” Polyhedron, vol. 22, no. 12, pp. 1529–1534, 2003. View at Google Scholar · View at Scopus
  289. G. Zhao, H. Lin, P. Yu, H. Sun, S. Zhu, and Y. Chen, “Comparison of the mode of action of a dinuclear platinum complex containing a pyridine derivative with its monomeric analog,” Chemico-Biological Interactions, vol. 116, no. 1-2, pp. 19–29, 1998. View at Publisher · View at Google Scholar · View at Scopus
  290. I. F. Duarte, I. Lamego, J. Marques, M. P. M. Marques, B. J. Blaise, and A. M. Gil, “Nuclear magnetic resonance (NMR) study of the effect of cisplatin on the metabolic profile of MG-63 osteosarcoma cells,” Journal of Proteome Research, vol. 9, no. 11, pp. 5877–5886, 2010. View at Publisher · View at Google Scholar · View at Scopus
  291. M. J. Cleare and J. D. Hoeschele, “Studies on the antitumor activity of group VIII transition metal complexes. I. Platinum (II) complexes,” Bioinorganic Chemistry, vol. 2, no. 3, pp. 187–210, 1973. View at Publisher · View at Google Scholar · View at Scopus
  292. T. W. Hambley, “The influence of structure on the activity and toxicity of Pt anti-cancer drugs,” Coordination Chemistry Reviews, vol. 166, pp. 181–223, 1997. View at Google Scholar · View at Scopus
  293. J. Zhang, D. Liu, Y. Li, J. Sun, L. Wang, and A. Zang, “Status of non-classical mononuclear platinum anticancer drug development,” Mini-Reviews in Medicinal Chemistry, vol. 9, no. 11, pp. 1357–1366, 2009. View at Publisher · View at Google Scholar · View at Scopus
  294. N. Farrell, L. R. Kelland, J. D. Roberts, and M. van Beusichem, “Activation of the trans geometry in platinum antitumor complexes: a survey of the cytotoxicity of trans complexes containing planar ligands in murine L1210 and human tumor panels and studies on their mechanism of action,” Cancer Research, vol. 52, no. 18, pp. 5065–5072, 1992. View at Google Scholar · View at Scopus
  295. S. Radulovic, Z. Tesic, and S. Manic, “Trans-platinum complexes as anticancer drugs: recent developments and future prospects,” Current Medicinal Chemistry, vol. 9, no. 17, pp. 1611–1618, 2002. View at Google Scholar · View at Scopus
  296. M. Coluccia and G. Natile, “Trans-platinum complexes in cancer therapy,” Anti-Cancer Agents in Medicinal Chemistry, vol. 7, no. 1, pp. 111–123, 2007. View at Publisher · View at Google Scholar · View at Scopus
  297. S. M. Aris and N. P. Farrell, “Towards antitumor active trans-platinum compounds,” European Journal of Inorganic Chemistry, vol. 2009, no. 10, pp. 1293–1302, 2009. View at Publisher · View at Google Scholar · View at Scopus
  298. B. T. Benedetti, S. Quintal, and N. P. Farrell, “Modulation of drug activation profiles through carboxylate ligand modification in cytotoxic trans-platinum planar amine compounds,” Dalton Transactions, vol. 40, no. 41, pp. 10983–10988, 2011. View at Publisher · View at Google Scholar
  299. C. Musetti, A. A. Nazarov, N. P. Farrell, and C. Sissi, “DNA reactivity profile of trans-platinum planar amine derivatives,” ChemMedChem, vol. 6, no. 7, pp. 1283–1290, 2011. View at Publisher · View at Google Scholar · View at Scopus
  300. R. F. Murphy, E. Komlodi-Pasztor, R. Robey, F. M. Balis, N. P. Farrell, and T. Fojo, “Retained platinum uptake and indifference to p53 status make novel transplatinum agents active in platinum-resistant cells compared to cisplatin and oxaliplatin,” Cell Cycle, vol. 11, no. 5, pp. 963–973, 2012. View at Publisher · View at Google Scholar
  301. M. T. Johnson, E. W. Neuse, C. E. J. van Rensburg, and E. Kreft, “Cell growth-inhibiting properties of selected carrier-bound, monoamine-coordinated platinum(II) compounds,” Journal of Inorganic and Organometallic Polymers and Materials, vol. 13, no. 2, pp. 55–67, 2003. View at Google Scholar · View at Scopus
  302. G. H. W. Milburn and M. R. Truter, “The crystal structures of cis- and trans-dichlorodiammineplatinum(II),” Journal of the Chemical Society A: Inorganic, Physical, Theoretical, pp. 1609–1616, 1966. View at Publisher · View at Google Scholar · View at Scopus
  303. S. Neidle, I. M. Ismail, and P. J. Sadler, “The structure of the antitumor complex cis(diammino) (1,1-cyclobutanedicarboxylato)-Pt(II): X ray and nmr studies,” Journal of Inorganic Biochemistry, vol. 13, no. 3, pp. 205–212, 1980. View at Publisher · View at Google Scholar · View at Scopus
  304. B. Beagley, D. W. J. Cruickshank, C. A. McAuliffe et al., “The crystal and molecular structure of cis-diammine-1,1-cyclobutanedicarboxoplatinum(II) [cis-Pt(NH3)2CBDCA]. Dynamic puckering of the cyclobutane ring,” Journal of Molecular Structure, vol. 130, no. 1-2, pp. 97–102, 1985. View at Google Scholar · View at Scopus
  305. L. A. E. Batista de Carvalho, M. P. M. Marques, C. Martin, S. F. Parker, and J. Tomkinson, “Inelastic neutron scattering study of PtII complexes displaying anticancer properties,” ChemPhysChem, vol. 12, no. 7, pp. 1334–1341, 2011. View at Publisher · View at Google Scholar · View at Scopus
  306. R. L. Benson and T. L. Gustafson, “Comparative study of the interactions of cisplatin and carboplatin with nucleotides using UV resonance Raman spectroscopy,” Biopolymers, vol. 33, no. 11, pp. 1631–1641, 1993. View at Publisher · View at Google Scholar · View at Scopus
  307. B. Giese, G. B. Deacon, J. Kuduk-Jaworska, and D. McNaughton, “Density functional theory and surface enhanced Raman spectroscopy characterization of novel platinum drugs,” Biopolymers, vol. 67, no. 4-5, pp. 294–297, 2002. View at Publisher · View at Google Scholar · View at Scopus
  308. B. Giese and D. McNaughton, “Interaction of anticancer drug cisplatin with guanine: density functional theory and surface-enhanced raman spectroscopy study,” Biopolymers, vol. 72, no. 6, pp. 472–489, 2003. View at Publisher · View at Google Scholar · View at Scopus
  309. O. Vrána, V. Mašek, V. Dražan, and V. Brabec, “Raman spectroscopy of DNA modified by intrastrand cross-links of antitumor cisplatin,” Journal of Structural Biology, vol. 159, no. 1, pp. 1–8, 2007. View at Publisher · View at Google Scholar · View at Scopus
  310. A. Barhoumi, D. Zhang, F. Tam, and N. J. Halas, “Surface-enhanced raman spectroscopy of DNA,” Journal of the American Chemical Society, vol. 130, no. 16, pp. 5523–5529, 2008. View at Publisher · View at Google Scholar · View at Scopus
  311. H. H. Zeng, Z. H. Xu, and K. Wang, “FT-Raman studies on the transformation of G-actin to F-actin, the binding of cisplatin and transplatin to F-actin and the effects of the conformation of F-actin,” International Journal of Biological Macromolecules, vol. 20, no. 2, pp. 107–113, 1997. View at Publisher · View at Google Scholar · View at Scopus
  312. Y. Yue, X. Chen, J. Qin, and X. Yao, “Spectroscopic investigation on the binding of antineoplastic drug oxaliplatin to human serum albumin and molecular modeling,” Colloids and Surfaces B: Biointerfaces, vol. 69, no. 1, pp. 51–57, 2009. View at Publisher · View at Google Scholar · View at Scopus
  313. K. D. Taylor, R. Goel, F. H. Shirazi et al., “Pressure tuning infrared spectroscopic study of cisplatin-induced structural changes in a phosphatidylserine model membrane,” British Journal of Cancer, vol. 72, no. 6, pp. 1400–1405, 1995. View at Google Scholar · View at Scopus
  314. M. P. M. Marques, F. Borges, A. M. Amorim da Costa, and L. A. E. Batista de Carvalho, “Vibrational spectroscopy studies on biologically relevant molecules: from anticancer agents to drugs of abuse,” in New Approaches in Biomedical Spectroscopy, pp. 338–363, American Chemical Society, 2007. View at Google Scholar
  315. A. M. Amado, M. M. Nolasco, and P. J. A. Ribeiro-Claro, “Probing pseudopolymorphic transitions in pharmaceutical solids using Raman spectroscopy: hydration and dehydration of theophylline,” Journal of Pharmaceutical Sciences, vol. 96, no. 5, pp. 1366–1379, 2007. View at Publisher · View at Google Scholar · View at Scopus
  316. C. Gendrin, Y. Roggo, and C. Collet, “Pharmaceutical applications of vibrational chemical imaging and chemometrics: a review,” Journal of Pharmaceutical and Biomedical Analysis, vol. 48, no. 3, pp. 533–553, 2008. View at Publisher · View at Google Scholar · View at Scopus
  317. F. Paiva-Martins, V. Rodrigues, R. Calheiros, and M. P. Marques, “Characterization of antioxidant olive oil biophenols by spectroscopic methods,” Journal of the Science of Food and Agriculture, vol. 91, no. 2, pp. 309–314, 2011. View at Publisher · View at Google Scholar · View at Scopus
  318. L. A. E. Batista de Carvalho and M. P. M. Marques, “Raman microspectroscopy: applications in life sciences,” in Image Analysis in Life Sciences, Research Signpost, 2009. View at Google Scholar
  319. Y. Wu, G. D. McEwen, S. Harihar, S. M. Baker, D. B. DeWald, and A. Zhou, “BRMS1 expression alters the ultrastructural, biomechanical and biochemical properties of MDA-MB-435 human breast carcinoma cells: an AFM and Raman microspectroscopy study,” Cancer Letters, vol. 293, no. 1, pp. 82–91, 2010. View at Publisher · View at Google Scholar · View at Scopus
  320. V. V. Pully, A. Lenferink, and C. Otto, “Hybrid Rayleigh, Raman and two-photon excited fluorescence spectral confocal microscopy of living cells,” Journal of Raman Spectroscopy, vol. 41, no. 6, pp. 599–608, 2010. View at Publisher · View at Google Scholar · View at Scopus
  321. A. B. Zoladek, R. K. Johal, S. Garcia-Nieto et al., “Label-free molecular imaging of immunological synapses between dendritic and T cells by Raman micro-spectroscopy,” The Analyst, vol. 135, no. 12, pp. 3205–3212, 2010. View at Publisher · View at Google Scholar · View at Scopus
  322. M. M. Mariani, P. J. R. Day, and V. Deckert, “Applications of modern micro-Raman spectroscopy for cell analyses,” Integrative Biology, vol. 2, no. 2-3, pp. 94–101, 2010. View at Publisher · View at Google Scholar · View at Scopus
  323. F. Draux, C. Gobinet, J. Sulé-Suso et al., “Raman spectral imaging of single cancer cells: probing the impact of sample fixation methods,” Analytical and Bioanalytical Chemistry, vol. 397, no. 7, pp. 2727–2737, 2010. View at Publisher · View at Google Scholar · View at Scopus
  324. S. Verrier, I. Notingher, J. M. Polak, and L. L. Hench, “In situ monitoring of cell death using Raman microspectroscopy,” Biopolymers, vol. 74, no. 1-2, pp. 157–162, 2004. View at Publisher · View at Google Scholar · View at Scopus
  325. L. Buriankova, Z. Nadova, D. Jancura et al., “Synchrotron based fourier-transform infrared microspectroscopy as sensitive technique for the detection of early apoptosis in U-87 MG cells,” Laser Physics Letters, vol. 7, no. 8, pp. 613–620, 2010. View at Publisher · View at Google Scholar · View at Scopus
  326. C. Pezzei, J. D. Pallua, G. Schaefer et al., “Characterization of normal and malignant prostate tissue by Fourier transform infrared microspectroscopy,” Molecular BioSystems, vol. 6, no. 11, pp. 2287–2295, 2010. View at Publisher · View at Google Scholar · View at Scopus
  327. K. Wehbe, R. Pineau, S. Eimer, A. Vital, H. Loiseau, and G. Déléris, “Differentiation between normal and tumor vasculature of animal and human glioma by FTIR imaging,” The Analyst, vol. 135, no. 12, pp. 3052–3059, 2010. View at Publisher · View at Google Scholar · View at Scopus
  328. G. Tosi, C. Conti, E. Giorgini et al., “FTIR microspectroscopy of melanocytic skin lesions: a preliminary study,” The Analyst, vol. 135, no. 12, pp. 3213–3219, 2010. View at Publisher · View at Google Scholar · View at Scopus
  329. J. Sulé-Suso and G. Cinque, “Infrared microspectroscopy in cancer diagnosis. Do we need synchrotron light?” Microscopy and Analysis, vol. 24, pp. 17–20, 2010. View at Google Scholar
  330. C. Matthäus, A. Kale, T. Chernenko, V. Torchilin, and M. Diem, “New ways of imaging uptake and intracellular fate of liposomal drug carrier systems inside individual cells, based on raman microscopy,” Molecular Pharmaceutics, vol. 5, no. 2, pp. 287–293, 2008. View at Publisher · View at Google Scholar · View at Scopus
  331. A. Tfayli, O. Piot, F. Pitre, and M. Manfait, “Follow-up of drug permeation through excised human skin with confocal Raman microspectroscopy,” European Biophysics Journal, vol. 36, no. 8, pp. 1049–1058, 2007. View at Publisher · View at Google Scholar · View at Scopus
  332. F. Draux, P. Jeannesson, A. Beljebbar et al., “Raman spectral imaging of single living cancer cells: a preliminary study,” The Analyst, vol. 134, no. 3, pp. 542–548, 2009. View at Publisher · View at Google Scholar · View at Scopus
  333. H. Nawaz, F. Bonnier, A. D. Meade, F. M. Lyng, and H. J. Byrne, “Comparison of subcellular responses for the evaluation and prediction of the chemotherapeutic response to cisplatin in lung adenocarcinoma using Raman spectroscopy,” The Analyst, vol. 136, no. 12, pp. 2450–2463, 2011. View at Publisher · View at Google Scholar · View at Scopus
  334. J. Sulé-Suso, D. Skingsley, G. D. Sockalingum et al., “FT-IR microspectroscopy as a tool to assess lung cancer cells response to chemotherapy,” Vibrational Spectroscopy, vol. 38, no. 1-2, pp. 179–184, 2005. View at Publisher · View at Google Scholar · View at Scopus
  335. H. Nawaz, F. Bonnier, P. Knief et al., “Evaluation of the potential of Raman microspectroscopy for prediction of chemotherapeutic response to cisplatin in lung adenocarcinoma,” The Analyst, vol. 135, no. 12, pp. 3070–3076, 2010. View at Publisher · View at Google Scholar · View at Scopus
  336. L. Corte, P. Rellini, L. Roscini, F. Fatichenti, and G. Cardinali, “Development of a novel, FTIR (Fourier transform infrared spectroscopy) based, yeast bioassay for toxicity testing and stress response study,” Analytica Chimica Acta, vol. 659, no. 1-2, pp. 258–265, 2010. View at Publisher · View at Google Scholar · View at Scopus
  337. A. Saha and V. V. Yakovlev, “Towards a rational drug design: Raman micro-spectroscopy analysis of prostate cancer cells treated with an aqueous extract of Nerium Oleander,” Journal of Raman Spectroscopy, vol. 40, no. 11, pp. 1459–1460, 2009. View at Publisher · View at Google Scholar · View at Scopus
  338. G. Bellisola, M. Della Peruta, M. Vezzalini et al., “Tracking infrared signatures of drugs in cancer cells by fourier transform microspectroscopy,” The Analyst, vol. 135, no. 12, pp. 3077–3086, 2010. View at Publisher · View at Google Scholar · View at Scopus
  339. H. Gao, F. Xia, C. Huang, and K. Lin, “Density functional theory calculations on the molecular structures and vibration spectra of platinum(II) antitumor drugs,” Spectrochimica Acta A: Molecular and Biomolecular Spectroscopy, vol. 78, no. 4, pp. 1234–1239, 2011. View at Publisher · View at Google Scholar · View at Scopus
  340. N. I. Dodoff, “A dft/ecp-small basis set modelling of cisplatin: molecular structure and vibrational spectrum,” Computational Molecular Bioscience, vol. 2, no. 2, pp. 35–44, 2012. View at Google Scholar
  341. D. Michalska and R. Wysokiński, “The prediction of Raman spectra of platinum(II) anticancer drugs by density functional theory,” Chemical Physics Letters, vol. 403, no. 1–3, pp. 211–217, 2005. View at Publisher · View at Google Scholar · View at Scopus
  342. V. P. Ting, M. Schmidtmann, C. C. Wilson, and M. T. Weller, “Cisplatin: polymorphism and structural insights into an important chemotherapeutic drug,” Angewandte Chemie - International Edition, vol. 49, no. 49, pp. 9408–9411, 2010. View at Publisher · View at Google Scholar · View at Scopus
  343. J. V. Burda, M. Zeizinger, and J. Leszczynski, “Hydration process as an activation of trans- and cisplatin complexes in anticancer treatment. DFT and ab initio computational study of thermodynamic and kinetic parameters,” Journal of Computational Chemistry, vol. 26, no. 9, pp. 907–914, 2005. View at Publisher · View at Google Scholar · View at Scopus
  344. R. Wysokiński, J. Kuduk-Jaworska, and D. Michalska, “Electronic structure, Raman and infrared spectra, and vibrational assignment of carboplatin. Density functional theory studies,” Journal of Molecular Structure: THEOCHEM, vol. 758, no. 2-3, pp. 169–179, 2006. View at Publisher · View at Google Scholar · View at Scopus
  345. E. C. Beret, R. R. Pappalardo, D. Marx, and E. S. Marcos, “Characterizing Pt-derived anticancer drugs from first principles: the case of oxaliplatin in aqueous solution,” ChemPhysChem, vol. 10, no. 7, pp. 1044–1052, 2009. View at Publisher · View at Google Scholar · View at Scopus
  346. R. Wysokiński, K. Hernik, R. Szostak, and D. Michalska, “Electronic structure and vibrational spectra of cis-diammine(orotato)platinum(II), a potential cisplatin analogue: DFT and experimental study,” Chemical Physics, vol. 333, no. 1, pp. 37–48, 2007. View at Publisher · View at Google Scholar · View at Scopus
  347. D. Bouvet, A. Michalowicz, S. Crauste-Manciet, D. Brossard, and K. Provost, “EXAFS and IR structural study of platinum-based anticancer drugs' degradation by diethyl dithiocarbamate,” Inorganic Chemistry, vol. 45, no. 8, pp. 3393–3398, 2006. View at Publisher · View at Google Scholar · View at Scopus
  348. M. Obata, M. Harada, H. Ohi, S. Hirohara, M. Gottchaldt, and S. Yano, “Extended X-ray absorption fine structure study on reaction of anti-tumor platinum complexes with reduced glutathione,” Chemical and Pharmaceutical Bulletin, vol. 57, no. 10, pp. 1107–1109, 2009. View at Publisher · View at Google Scholar · View at Scopus
  349. K. Provost, D. Bouvet-Muller, S. Crauste-Manciet et al., “EXAFS structural study of platinum-based anticancer drugs degradation in presence of sulfur nucleophilic species,” Biochimie, vol. 91, no. 10, pp. 1301–1306, 2009. View at Publisher · View at Google Scholar · View at Scopus
  350. E. Dartyge, C. Depautex, J. M. Dubuisson et al., “X-ray absorption in dispersive mode: a new spectrometer and a data acquisition system for fast kinetics,” Nuclear Instruments and Methods in Physics Research Section A: Accelerators, Spectrometers, Detectors and Associated Equipment, vol. 246, no. 1–3, pp. 452–460, 1986. View at Google Scholar · View at Scopus
  351. G. Cossa, L. Gatti, F. Zunino, and P. Perego, “Strategies to improve the efficacy of platinum compounds,” Current Medicinal Chemistry, vol. 16, no. 19, pp. 2355–2365, 2009. View at Publisher · View at Google Scholar · View at Scopus
  352. E. Gabano, M. Ravera, and D. Osella, “The drug targeting and delivery approach applied to Pt-antitumour complexes. A coordination point of view,” Current Medicinal Chemistry, vol. 16, no. 34, pp. 4544–4580, 2009. View at Publisher · View at Google Scholar · View at Scopus
  353. G. N. C. Chiu, M. Y. Wong, L. U. Ling et al., “Lipid-based nanoparticulate systems for the delivery of anti-cancer drug cocktails: implications on pharmacokinetics and drug toxicities,” Current Drug Metabolism, vol. 10, no. 8, pp. 861–874, 2009. View at Publisher · View at Google Scholar · View at Scopus
  354. N. P. Farrell, “Platinum formulations as anticancer drugs clinical and pre-clinical studies,” Current Topics in Medicinal Chemistry, vol. 11, no. 21, pp. 2623–2631, 2011. View at Publisher · View at Google Scholar
  355. C. Sessa, C. Minoia, A. Ronchi et al., “Phase I clinical and pharmacokinetic study of the oral platinum analogue JM216 given daily for 14 days,” Annals of Oncology, vol. 9, no. 12, pp. 1315–1322, 1998. View at Publisher · View at Google Scholar · View at Scopus
  356. A. A. Bhirde, S. Patel, A. A. Sousa et al., “Distribution and clearance of PEG-single-walled carbon nanotube cancer drug delivery vehicles in mice,” Nanomedicine, vol. 5, no. 10, pp. 1535–1546, 2010. View at Publisher · View at Google Scholar · View at Scopus
  357. J. Lin, Y. Li, S. Feng et al., “Raman spectroscopic analysis of cytotoxic effect of cisplatin-treated leukemic cells,” in 8th International Conference on Photonics and Imaging in Biology and Medicine (PIBM '09), Proceedings of SPIE, Wuhan, China, August 2009. View at Publisher · View at Google Scholar · View at Scopus
  358. Z. H. Tao, H. L. Yao, G. W. Wang et al., “Using Raman spectroscopy to analyze apoptosis of gastric cancer cells induced by cisplatin,” Guang Pu Xue Yu Guang Pu Fen Xi, vol. 29, no. 9, pp. 2442–2445, 2009. View at Publisher · View at Google Scholar · View at Scopus