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Journal of Chemistry
Volume 2016 (2016), Article ID 7508724, 7 pages
http://dx.doi.org/10.1155/2016/7508724
Research Article

Novel Palladium(II) and Platinum(II) Complexes with a Fluoropiperazinyl Based Ligand Exhibiting High Cytotoxicity and Anticancer Activity In Vitro

1Department of Chemistry, Hashemite University, P.O. Box 150459, Zarqa 13115, Jordan
2Department of Chemistry and Earth Sciences, College of Arts and Sciences, Qatar University, P.O. Box 2713, Doha, Qatar
3Department of Physiology and Biochemistry, The University of Jordan, Amman 11942, Jordan
4Department of Biology and Biotechnology, Hashemite University, Zarqa 13115, Jordan

Received 10 December 2015; Accepted 31 January 2016

Academic Editor: Josefina Pons

Copyright © 2016 Kayed A. Abu-Safieh et al. 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. Á. M. Montaña and C. Batalla, “The rational design of anticancer platinum complexes: the importance of the structure-activity relationship,” Current Medicinal Chemistry, vol. 16, no. 18, pp. 2235–2260, 2009. View at Publisher · View at Google Scholar · View at Scopus
  2. 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
  3. 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. 791–794, 1989. View at Google Scholar
  4. G. Zhao, H. Lin, Y. Ping 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
  5. 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
  6. Y.-P. Ho, K. K. W. To, S. C. F. Au-Yeung, X. Wang, G. Lin, and X. Han, “Potential new antitumor agents from an innovative combination of demethylcantharidin, a modified traditional chinese medicine, with a platinum moiety,” Journal of Medicinal Chemistry, vol. 44, no. 13, pp. 2065–2068, 2001. View at Publisher · View at Google Scholar · View at Scopus
  7. T. V. Polyanskaya, I. Kazhdan, D. M. Motley, and J. A. Walmsley, “Synthesis, characterization and cytotoxicity studies of palladium(II)–proflavine complexes,” Journal of Inorganic Biochemistry, vol. 104, no. 11, pp. 1205–1213, 2010. View at Publisher · View at Google Scholar · View at Scopus
  8. F. Z. 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. 791–794, 1989. View at Google Scholar
  9. 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. 745–149, 1999. View at Google Scholar
  10. A. S. Abu-Surrah, H. H. Al-Sa'doni, and M. Y. Abdalla, “Palladium based chemotherapeutic agents. Routes towards complexes with good antitumor activity,” Cancer Therapy, vol. 6, pp. 1–10, 2008. View at Google Scholar
  11. A. S. Abu-Surrah, T. A. K. Al-Allaf, L. J. Rashan, M. Klinga, and M. Leskelä, “Synthesis, crystal structure and initial biological evaluation of the new enantiomerically pure chiral palladium(II) complex trans-bis{endo-(1R)-1,7,7-trimethylbicyclo[2.2.1]-heptan-2-amino}palladium(II)dichloride,” European Journal of Medicinal Chemistry, vol. 37, no. 11, pp. 919–922, 2002. View at Publisher · View at Google Scholar
  12. T. A. K. Al-Allaf and L. J. Rashan, “Synthesis and cytotoxic evaluation of the first trans-palladium(II) complex with naturally occurring alkaloid harmine,” European Journal of Medicinal Chemistry, vol. 33, no. 10, pp. 817–820, 1998. View at Publisher · View at Google Scholar · View at Scopus
  13. T. A. K Al-Allaf, L. J. Rashan, M. T. Ayoub, and M. H. Adday, U.K. Patent No.2 304 712, 1997.
  14. T. A. Connors, M. Jones, W. C. J. Ross, P. D. Braddock, A. R. Khokhar, and M. L. Tobe, “New platinum complexes with anti-tumour activity,” Chemico-Biological Interactions, vol. 5, no. 6, pp. 415–424, 1972. View at Publisher · View at Google Scholar · View at Scopus
  15. S. J. Meischen, G. R. Gale, L. M. Lake et al., “Antileukemic properties of organoplatinum complexes,” Journal of the National Cancer Institute, vol. 57, no. 4, pp. 841–845, 1976. View at Google Scholar · View at Scopus
  16. M. V. de Almeida, J. D. S. Chaves, A. P. S. Fontes, E. T. César, and M. Gielen, “Synthesis and characterization of platinum(II) complexes from trifluoromethyl phenylenediamine, picoline and N-benzyl ethylenediamine derivatives,” Journal of the Brazilian Chemical Society, vol. 17, no. 7, pp. 1266–1273, 2006. View at Google Scholar · View at Scopus
  17. R. J. Abdel-Jalil, R. A. Al-Qawasmeh, W. Voelter, P. Heeg, M. M. El-Abadelah, and S. S. Sabri, “Synthesis and properties of some 2,3-disubstituted 6-fluoro-7-(4-methyl-1-piperazinyl)quinoxalines,” Journal of Heterocyclic Chemistry, vol. 37, no. 5, pp. 1273–1275, 2000. View at Publisher · View at Google Scholar · View at Scopus
  18. R. J. Abdel-Jalil and W. Voelter, “Synthesis of new 2-ferrocenyl-5-fluoro-6-(4-substituted-1-piperazinyl)-1H-benzimidazoles of potential biological interest,” Journal of Heterocyclic Chemistry, vol. 42, no. 1, pp. 67–71, 2005. View at Publisher · View at Google Scholar · View at Scopus
  19. M. P. Wentland, D. M. Bailey, J. B. Cornett, R. A. Dobson, R. G. Powles, and R. B. Wagner, “Novel amino-substituted 3-quinolinecarboxylic acid antibacterial agents: synthesis and structure-activity relationships,” Journal of Medicinal Chemistry, vol. 27, no. 9, pp. 1103–1108, 1984. View at Publisher · View at Google Scholar · View at Scopus
  20. G. A. Daxhelet, M. M. Coene, P. P. Hoet, and C. G. Cocito, “Spectrofluorometry of dyes with DNAs of different base composition and conformation,” Analytical Biochemistry, vol. 179, no. 2, pp. 401–403, 1989. View at Publisher · View at Google Scholar · View at Scopus
  21. R. Iemura and H. Ohtaka, “Quantitative structure-activity relationships of H1-antihistaminic benzimidazole derivatives,” Chemical and Pharmaceutical Bulletin, vol. 37, no. 4, pp. 967–972, 1989. View at Publisher · View at Google Scholar · View at Scopus
  22. K. Lappalainen, K. Yliheikkilä, A. S. Abu-Surrah et al., “Iron(II)- and cobalt(II) complexes with tridentate bis(imino)pyridine nitrogen ligands bearing chiral bulky aliphatic and aromatic substituents: crystal structure of [CoCl2{2, 6-bis[R-(+)-(bornylimino)methyl]pyridine}],” Zeitschrift für Anorganische und Allgemeine Chemie, vol. 631, no. 4, pp. 763–768, 2005. View at Publisher · View at Google Scholar
  23. A. S. Abu-Surrah, K. A. Abu Safieh, I. M. Ahmad et al., “New palladium(II) complexes bearing pyrazole-based Schiff base ligands: synthesis, characterization and cytotoxicity,” European Journal of Medicinal Chemistry, vol. 45, no. 2, pp. 471–475, 2010. View at Publisher · View at Google Scholar · View at Scopus
  24. 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 Publisher · View at Google Scholar · View at Scopus
  25. T. A. K. Al-Allaf, L. J. Rashan, A. S. Abu-Surrah, R. Fawzi, and M. Steiman, “Chemical properties and cytotoxic activity of complexes of platinum(II) and palladium(II) containing dmso and various anions; synthesis and structural characterization of [Pt(dmso)2{O2(CO)2CCH2CH2CH2}],” Transition Metal Chemistry, vol. 23, no. 4, pp. 403–406, 1998. View at Publisher · View at Google Scholar
  26. M. M. El-Abadelah, S. S. Sabri, M. H. Abu-Zarga, and R. J. Abdel-Jalil, “Substituted benzimidazoles. Part 1. Synthesis and properties of some 2-aryl-5-fluoro-6-(4-methyl-1-piperazinyl)-1H-benzimidazoles,” Heterocycles, vol. 41, no. 2, pp. 2713–2728, 1995. View at Publisher · View at Google Scholar
  27. T. Mosmann, “Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays,” Journal of Immunological Methods, vol. 65, no. 1-2, pp. 55–63, 1983. View at Publisher · View at Google Scholar · View at Scopus
  28. G. Fotakis and J. A. Timbrell, “In vitro cytotoxicity assays: comparison of LDH, neutral red, MTT and protein assay in hepatoma cell lines following exposure to cadmium chloride,” Toxicology Letters, vol. 160, no. 2, pp. 171–177, 2006. View at Publisher · View at Google Scholar
  29. R. Freshney, Culture of Animal Cells: A Manual of Basic Technique and Specialized Applications, John Wiley & Sons, Hoboken, NJ, USA, 2000.
  30. V. Alverdi, L. Giovagnini, C. Marzano et al., “Characterization studies and cytotoxicity assays of Pt(II) and Pd(II) dithiocarbamate complexes by means of FT-IR, NMR spectroscopy and mass spectrometry,” Journal of Inorganic Biochemistry, vol. 98, no. 6, pp. 1117–1128, 2004. View at Publisher · View at Google Scholar · View at Scopus
  31. N. A. P. Franken, H. M. Rodermond, J. Stap, J. Haveman, and C. van Bree, “Clonogenic assay of cells in vitro,” Nature Protocols, vol. 1, no. 5, pp. 2315–2319, 2006. View at Publisher · View at Google Scholar · View at Scopus
  32. A. S. Abu-Surrah, G. Eckert, W. Pechhold, W. Wilke, and B. Rieger, “Ultrahigh molecular weight alternating propene/ethene/carbon monoxide terpolymers with elastic properties,” Macromolecular Rapid Communications, vol. 17, no. 8, pp. 559–565, 1996. View at Publisher · View at Google Scholar · View at Scopus