Table of Contents Author Guidelines Submit a Manuscript
Advances in Chemistry
Volume 2014 (2014), Article ID 589686, 20 pages
http://dx.doi.org/10.1155/2014/589686
Review Article

The Biological Side of Water-Soluble Arene Ruthenium Assemblies

1Institut de Chimie, Université de Neuchâtel, Avenue de Bellevaux 51, 2000 Neuchâtel, Switzerland
2Departement für Chemie und Biochemie, Universität Bern, Freiestraße 3, 3012 Berne, Switzerland

Received 4 March 2014; Accepted 23 April 2014; Published 17 July 2014

Academic Editor: Fazlul Haq

Copyright © 2014 Bruno Therrien and Julien Furrer. 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. B. Rosenberg, L. van Camp, E. B. Grimley, and A. J. Thomson, “The inhibition of growth or cell division in Escherichia coli by different ionic species of platinum(IV) complexes,” The Journal of Biological Chemistry, vol. 242, no. 6, pp. 1347–1352, 1967. View at Google Scholar · View at Scopus
  2. 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
  3. E. R. Jamieson and S. J. Lippard, “Structure, recognition, and processing of cisplatin-DNA adducts,” Chemical Reviews, vol. 99, no. 9, pp. 2467–2498, 1999. View at Publisher · View at Google Scholar · View at Scopus
  4. 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
  5. J. D. Roberts, J. Peroutka, G. Beggiolin, C. Manzotti, L. Piazzoni, and N. Farrell, “Comparison of cytotoxicity and cellular accumulation of polynuclear platinum complexes in L1210 murine leukemia cell lines,” Journal of Inorganic Biochemistry, vol. 77, no. 1-2, pp. 47–50, 1999. View at Publisher · View at Google Scholar · View at Scopus
  6. J. Reedijk, “Improved understanding in platinium antitumour chemistry,” Chemical Communications, no. 7, pp. 801–806, 1996. View at Publisher · View at Google Scholar
  7. S. M. Cohen and S. J. Lippard, “Cisplatin: from DNA damage to cancer chemotherapy,” Progress in Nucleic Acid Research and Molecular Biology, vol. 67, pp. 93–130, 2001. View at Publisher · View at Google Scholar
  8. Z. H. Siddik, “Cisplatin: mode of cytotoxic action and molecular basis of resistance,” Oncogene, vol. 22, no. 47, pp. 7265–7279, 2003. View at Publisher · View at Google Scholar · View at Scopus
  9. L. R. Kelland, G. Abel, M. J. McKeage et al., “Preclinical antitumor evaluation of bis-acetato-ammine-dichloro- cyclohexylamine platinum(IV): an orally active platinum drug,” Cancer Research, vol. 53, no. 11, pp. 2581–2586, 1993. View at Google Scholar · View at Scopus
  10. J. Holford, F. Raynaud, B. 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
  11. S. B. Howell, “The design and development of the tumor-targeting nanopolymer dach platinum conjugate AP5346 (ProlindacTM),” in Platinum and Other Heavy Metal Compounds in Cancer Chemotherapy, A. Bonetti, R. Leone, F. Muggia, and S. B. Howell, Eds., Cancer Drug Discovery and Development, pp. 33–39, Humana Press, New York, NY, USA, 2009. View at Google Scholar
  12. M. Serova, A. Ghoul, K. Rezai et al., “In vitro anti-proliferative effects of Prolindac, a novel DACH-platinum linked polymer compound, as a single agent and in combination with other anti-cancer drugs,” in Platinum and Other Heavy Metal Compounds in Cancer Chemotherapy: Molecular Mechanism and Clinical Applications, A. Bonetti, R. Leone, F. Muggia, and S. B. Howell, Eds., pp. 41–47, Humana Press, New York, NY, USA, 2009. View at Google Scholar
  13. T. Boulikas, “Low toxicity and anticancer activity of a novel liposomal cisplatin (Lipoplatin) in mouse xenografts,” Oncology Reports, vol. 12, pp. 3–12, 2004. View at Google Scholar
  14. T. Boulikas, “Molecular mechanisms of cisplatin and its liposomally encapuslated form, LipoplatinTM as a chemotherapy and antiangiogenesis drug,” Cancer Therapy, vol. 5, pp. 351–376, 2007. View at Google Scholar
  15. N. Farrell, Metal Ions in Biolgical Systems, Vol 42: Metal Complexes in Tumor Diagnosis and as Anticancer Agents, 2004.
  16. 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
  17. J. D. Roberts, J. Peroutka, and N. Farrell, “Cellular pharmacology of polynuclear platinum anti-cancer agents,” Journal of Inorganic Biochemistry, vol. 77, no. 1-2, pp. 51–57, 1999. View at Publisher · View at Google Scholar · View at Scopus
  18. 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
  19. N. Bertrand and J. C. Leroux, “The journey of a drug-carrier in the body: an anatomo-physiological perspective,” Journal of Controlled Release, vol. 161, no. 2, pp. 152–163, 2012. View at Publisher · View at Google Scholar · View at Scopus
  20. K. Kataoka, A. Harada, and Y. Nagasaki, “Block copolymer micelles for drug delivery: design, characterization and biological significance,” Advanced Drug Delivery Reviews, vol. 47, no. 1, pp. 113–131, 2001. View at Publisher · View at Google Scholar · View at Scopus
  21. H. Maeda, “The enhanced permeability and retention (EPR) effect in tumor vasculature: the key role of tumor-selective macromolecular drug targeting,” Advances in Enzyme Regulation, vol. 41, pp. 189–207, 2001. View at Publisher · View at Google Scholar · View at Scopus
  22. H. Uchino, Y. Matsumura, T. Negishi et al., “Cisplatin-incorporating polymeric micelles (NC-6004) can reduce nephrotoxicity and neurotoxicity of cisplatin in rats,” British Journal of Cancer, vol. 93, no. 6, pp. 678–687, 2005. View at Publisher · View at Google Scholar · View at Scopus
  23. K. J. Haxton and H. M. Burt, “Polymeric drug delivery of platinum-based anticancer agents,” Journal of Pharmaceutical Sciences, vol. 98, no. 7, pp. 2299–2316, 2009. View at Publisher · View at Google Scholar · View at Scopus
  24. R. Haag and F. Kratz, “Polymer therapeutics: concepts and applications,” Angewandte Chemie&International Edition, vol. 45, no. 8, pp. 1198–1215, 2006. View at Publisher · View at Google Scholar · View at Scopus
  25. D. E. Discher and A. Eisenberg, “Polymer vesicles,” Science, vol. 297, no. 5583, pp. 967–973, 2002. View at Publisher · View at Google Scholar · View at Scopus
  26. P. Govender, B. Therrien, and G. S. Smith, “Bio-metallodendrimers—emerging strategies in metal-based drug design,” European Journal of Inorganic Chemistry, no. 17, pp. 2853–2862, 2012. View at Publisher · View at Google Scholar · View at Scopus
  27. F. Arnesano and G. Natile, “Mechanistic insight into the cellular uptake and processing of cisplatin 30 years after its approval by FDA,” Coordination Chemistry Reviews, vol. 253, no. 15-16, pp. 2070–2081, 2009. View at Publisher · View at Google Scholar · View at Scopus
  28. S. Bhattacharyya, R. A. Kudgus, R. Bhattacharya, and P. Mukherjee, “Inorganic nanoparticles in cancer therapy,” Pharmaceutical Research, vol. 28, no. 2, pp. 237–259, 2011. View at Publisher · View at Google Scholar · View at Scopus
  29. D. K. Chan, D. M. Lieberman, S. Musatov, J. A. Goldfein, S. H. Selesnick, and M. G. Kaplitt, “Protection against cisplatin-induced ototoxicity by adeno-associated virus-mediated delivery of the X-linked inhibitor of apoptosis protein is not dependent on caspase inhibition,” Otology & Neurotology, vol. 28, no. 3, pp. 417–425, 2007. View at Publisher · View at Google Scholar · View at Scopus
  30. K. Ajima, M. Yudasaka, T. Murakami, A. Maigné, K. Shiba, and S. Iijima, “Carbon nanohorns as anticancer drug carriers,” Molecular Pharmaceutics, vol. 2, no. 6, pp. 475–480, 2005. View at Publisher · View at Google Scholar · View at Scopus
  31. R. P. Feazell, N. Nakayama-Ratchford, H. Dai, and S. J. Lippard, “Soluble single-walled carbon nanotubes as longboat delivery systems for platinum(IV) anticancer drug design,” Journal of the American Chemical Society, vol. 129, no. 27, pp. 8438–8439, 2007. View at Publisher · View at Google Scholar · View at Scopus
  32. B. Therrien, “Arene ruthenium cages: boxes full of surprises,” European Journal of Inorganic Chemistry, vol. 2009, no. 17, pp. 2445–2453, 2009. View at Publisher · View at Google Scholar
  33. M. Fujita, J. Yazaki, and K. Ogura, “Preparation of a macrocyclic polynuclear complex, [(en)Pd(4,4-bpy)]4(NO3)8 (en = ethylenediamine, bpy = bipyridine), which recognizes an organic molecule in aqueous media,” Journal of the American Chemical Society, vol. 112, pp. 5645–5646, 1990. View at Publisher · View at Google Scholar
  34. M. Fujita, D. Oguro, M. Miyazawa, H. Oka, K. Yamaguchi, and K. Ogura, “Self assembly of ten molecules into nanometre-sized organic host frameworks,” Nature, vol. 378, no. 6556, pp. 469–471, 1995. View at Publisher · View at Google Scholar · View at Scopus
  35. Y. M. Jeon, J. Kim, D. Whang, and K. Kim, “Molecular container assembly capable of conrolling binding and release of its guest molecules: Reversible encapsulation of organic molecules in sodium ion complexed cucurbituril,” Journal of the American Chemical Society, vol. 118, no. 40, pp. 9790–9791, 1996. View at Publisher · View at Google Scholar · View at Scopus
  36. F. A. Cotton, C. Lin, and C. A. Murillo, “Supramolecular arrays based on dimetal building units,” Accounts of Chemical Research, vol. 34, no. 10, pp. 759–771, 2001. View at Publisher · View at Google Scholar · View at Scopus
  37. M. Fujita, M. Tominaga, A. Hori, and B. Therrien, “Coordination assemblies from a Pd(II)-cornered square complex,” Accounts of Chemical Research, vol. 38, no. 4, pp. 369–378, 2005. View at Publisher · View at Google Scholar · View at Scopus
  38. C. Y. Su, Y. P. Cai, C. L. Chen, M. D. Smith, W. Kaim, and H. C. zur Loye, “Ligand-directed molecular architectures: Self-assembly of two-dimensional rectangular metallacycles and three-dimensional trigonal or tetragonal prisms,” Journal of the American Chemical Society, vol. 125, no. 28, pp. 8595–8613, 2003. View at Publisher · View at Google Scholar · View at Scopus
  39. R. Chakrabarty, P. S. Mukherjee, and P. J. Stang, “Supramolecular coordination: self-assembly of finite two- and three-dimensional ensembles,” Chemical Reviews, vol. 111, no. 11, pp. 6810–6918, 2011. View at Publisher · View at Google Scholar · View at Scopus
  40. J. E. M. Lewis, E. L. Gavey, S. A. Cameron, and J. D. Crowley, “Stimuli-responsive Pd2L4 metallosupramolecular cages: towards targeted cisplatin drug delivery,” Chemical Science, vol. 3, no. 3, pp. 778–784, 2012. View at Publisher · View at Google Scholar · View at Scopus
  41. F. P. Dwyer, E. C. Gyarfas, W. P. Rogers, and J. H. Koch, “Biological activity of complex ions,” Nature, vol. 170, no. 4318, pp. 190–191, 1952. View at Publisher · View at Google Scholar · View at Scopus
  42. M. J. Clarke, “Oncological implications of the chemistry of ruthenium,” Metals Ions in Biological System, vol. 11, pp. 231–283, 1980. View at Google Scholar
  43. E. S. Antonarakis and A. Emadi, “Ruthenium-based chemotherapeutics: are they ready for prime time?” Cancer Chemotherapy and Pharmacology, vol. 66, no. 1, pp. 1–9, 2010. View at Publisher · View at Google Scholar · View at Scopus
  44. A. Bergamo and G. Sava, “Ruthenium anticancer compounds: myths and realities of the emerging metal-based drugs,” Dalton Transactions, vol. 40, no. 31, pp. 7817–7823, 2011. View at Publisher · View at Google Scholar · View at Scopus
  45. W. H. Ang, A. Casini, G. Sava, and P. J. Dyson, “Organometallic ruthenium-based antitumor compounds with novel modes of action,” Journal of Organometallic Chemistry, vol. 696, no. 5, pp. 989–998, 2011. View at Publisher · View at Google Scholar · View at Scopus
  46. J. M. Rademaker-Lakhai, D. van den Bongard, D. Pluim, J. H. Beijnen, and J. H. M. Schellens, “A phase I and pharmacological study with imidazolium-trans-DMSO-imidazole-tetrachlororuthenate, a novel ruthenium anticancer agent,” Clinical Cancer Research, vol. 10, no. 11, pp. 3717–3727, 2004. View at Publisher · View at Google Scholar · View at Scopus
  47. C. G. Hartinger, M. A. Jakupec, S. Zorbas-Seifried et al., “KP1019, a new redox-active anticancer agent—preclinical development and results of a clinical phase I study in tumor patients,” Chemistry and Biodiversity, vol. 5, no. 10, pp. 2140–2155, 2008. View at Publisher · View at Google Scholar · View at Scopus
  48. P. Heffeter, B. Atil, K. Kryeziu et al., “The ruthenium compound KP1339 potentiates the anticancer activity of sorafenib in vitro and in vivo,” European Journal of Cancer, vol. 49, no. 15, pp. 3366–3375, 2013. View at Publisher · View at Google Scholar · View at Scopus
  49. G. Süss-Fink, “Arene ruthenium complexes as anticancer agents,” Dalton Transactions, vol. 39, no. 7, pp. 1673–1688, 2010. View at Publisher · View at Google Scholar · View at Scopus
  50. C. S. Allardyce, P. J. Dyson, D. J. Ellis, and S. L. Heath, “[Ru(eta)6-p-cymene)Cl-2(pta)] (pta=1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane): a water soluble compound that exhibits pH dependent DNA binding providing selectivity for diseased cells,” Chemical Communications, pp. 1396–1397, 2001. View at Google Scholar
  51. C. Scolaro, A. Bergamo, L. Brescacin et al., “In vitro and in vivo evaluation of ruthenium(II)-arene PTA complexes,” Journal of Medicinal Chemistry, vol. 48, no. 12, pp. 4161–4171, 2005. View at Publisher · View at Google Scholar · View at Scopus
  52. W. H. Ang, E. Daldini, C. Scolaro, R. Scopelliti, L. Juillerat-Jeannerat, and P. J. Dyson, “Development of organometallic ruthenium-arene anticancer drugs that resist hydrolysis,” Inorganic Chemistry, vol. 45, no. 22, pp. 9006–9013, 2006. View at Publisher · View at Google Scholar · View at Scopus
  53. R. E. Aird, J. Cummings, A. A. Ritchie et al., “In vitro and in vivo activity and cross resistance profiles of novel ruthenium (II) organometallic arene complexes in human ovarian cancer,” British Journal of Cancer, vol. 86, no. 10, pp. 1652–1657, 2002. View at Publisher · View at Google Scholar · View at Scopus
  54. R. A. Zelonka and M. C. Baird, “Reactions of benzene complexes of ruthernium(II),” Journal of Organometallic Chemistry, vol. 35, no. 1, pp. C43–C46, 1972. View at Publisher · View at Google Scholar · View at Scopus
  55. G. Süss-Fink, “Water-soluble arene ruthenium complexes: from serendipity to catalysis and drug design,” Journal of Organometallic Chemistry, vol. 751, pp. 2–19, 2014. View at Publisher · View at Google Scholar
  56. G. Süss-Fink and B. Therrien, “Dinuclear ruthenium and osmium arene trihydrido complexes: versatile water-soluble synthons in organometallic chemistry,” Organometallics, vol. 26, no. 4, pp. 766–774, 2007. View at Publisher · View at Google Scholar · View at Scopus
  57. F. A. Egbewande, L. E. H. Paul, B. Therrien, and J. Furrer, “Synthesis, characterization and cytotoxicity of (η6-p-cymene)ruthenium(II) complexes of α-amino acids,” European Journal of Inorganic Chemistry, vol. 2014, no. 7, pp. 1174–1184, 2014. View at Google Scholar
  58. H. Yan, G. Süss-Fink, A. Neels, and H. Stoeckli-Evans, “Mono-, di- and tetra-nuclear p-cymeneruthenium complexes containing oxalato ligands,” Journal of the Chemical Society, Dalton Transactions, vol. 1997, no. 22, pp. 4345–4350, 1997. View at Publisher · View at Google Scholar
  59. F. Linares, M. A. Galindo, S. Galli, M. A. Romero, J. A. R. Navarro, and E. Barea, “Tetranuclear coordination assemblies based on half-sandwich ruthenium(II) complexes: noncovalent binding to DNA and cytotoxicity,” Inorganic Chemistry, vol. 48, no. 15, pp. 7413–7420, 2009. View at Publisher · View at Google Scholar · View at Scopus
  60. J. Mattsson, P. Govindaswamy, A. K. Renfrew et al., “Synthesis, molecular structure and anticancer activity of cationic arene ruthenium metallarectangles,” Organometallics, vol. 28, no. 15, pp. 4350–4357, 2009. View at Publisher · View at Google Scholar · View at Scopus
  61. B. H. Northrop, Y.-R. Zheng, K.-W. Chi, and P. J. Stang, “Self-organization in coordination-driven self-assembly,” Accounts of Chemical Research, vol. 42, no. 10, pp. 1554–1563, 2009. View at Publisher · View at Google Scholar
  62. V. Vajpayee, Y. H. Song, M. H. Lee et al., “Self-assembled arene-ruthenium-based rectangles for the selective sensing of multi-carboxylate anions,” Chemistry, vol. 17, no. 28, pp. 7837–7844, 2011. View at Publisher · View at Google Scholar · View at Scopus
  63. V. Vajpayee, Y. H. Song, Y. J. Jung et al., “Coordination-driven self-assembly of ruthenium-based molecular-rectangles: synthesis, characterization, photo-physical and anticancer potency studies,” Dalton Transactions, vol. 41, no. 10, pp. 3046–3052, 2012. View at Publisher · View at Google Scholar · View at Scopus
  64. V. Vajpayee, S. Lee, S. Kim et al., “Self-assembled metalla-rectangles bearing azodipyridyl ligands: synthesis, characterization and antitumor activity,” Dalton Transactions, vol. 42, no. 2, pp. 466–475, 2013. View at Publisher · View at Google Scholar · View at Scopus
  65. V. Vajpayee, S. M. Lee, J. W. Park et al., “Growth inhibitory activity of a bis-benzimidazole-bridged arene ruthenium metalla-rectangle and -prism,” Organometallics, vol. 32, no. 6, pp. 1563–1566, 2013. View at Publisher · View at Google Scholar · View at Scopus
  66. N. P. E. Barry, F. Edafe, and B. Therrien, “Anticancer activity of tetracationic arene ruthenium metalla-cycles,” Dalton Transactions, vol. 40, no. 27, pp. 7172–7180, 2011. View at Publisher · View at Google Scholar · View at Scopus
  67. G. Gupta, B. Murray, P. Dyson, and B. Therrien, “Synthesis, molecular structure and cytotoxicity of molecular materials based on water soluble half-sandwich Rh(III) and Ir(III) tetranuclear metalla-cycles,” Materials, vol. 6, no. 11, pp. 5352–5366, 2013. View at Publisher · View at Google Scholar
  68. N. P. E. Barry, F. Edafe, P. J. Dyson, and B. Therrien, “Anticancer activity of osmium metalla-rectangles,” Dalton Transactions, vol. 39, no. 11, pp. 2816–2820, 2010. View at Publisher · View at Google Scholar · View at Scopus
  69. P. Govindaswamy, D. Linder, J. Lacour, G. Süss-Fink, and B. Therrien, “Self-assembled hexanuclear arene ruthenium metallo-prisms with unexpected double helical chirality,” Chemical Communications, no. 45, pp. 4691–4693, 2006. View at Publisher · View at Google Scholar · View at Scopus
  70. N. P. E. Barry, M. Austeri, J. Lacour, and B. Therrien, “Highly efficient NMR enantiodiscrimination of chiral octanuclear metalla-boxes in polar solvent,” Organometallics, vol. 28, no. 16, pp. 4894–4897, 2009. View at Publisher · View at Google Scholar · View at Scopus
  71. N. P. E. Barry, N. H. Abd Karim, R. Vilar, and B. Therrien, “Interactions of ruthenium coordination cubes with DNA,” Dalton Transactions, no. 48, pp. 10717–10719, 2009. View at Publisher · View at Google Scholar · View at Scopus
  72. N. P. E. Barry, J. Furrer, J. Freudenreich, G. Süss-Fink, and B. Therrien, “Designing the host-guest properties of tetranuclear arene ruthenium metalla-rectangles to accommodate a pyrene molecule,” European Journal of Inorganic Chemistry, vol. 2010, no. 5, pp. 725–728, 2010. View at Publisher · View at Google Scholar
  73. C. S. Johnson, “Diffusion ordered nuclear magnetic resonance spectroscopy: principles and applications,” Progress in Nuclear Magnetic Resonance Spectroscopy, vol. 34, no. 3-4, pp. 203–256, 1999. View at Publisher · View at Google Scholar
  74. Y. Cohen, L. Avram, and L. Frish, “Diffusion NMR spectroscopy in supramolecular and combinatorial chemistry: an old parameter—new insights,” Angewandte Chemie, vol. 44, no. 4, pp. 520–554, 2005. View at Publisher · View at Google Scholar · View at Scopus
  75. N. P. E. Barry, J. Furrer, and B. Therrien, “In- and out-of-cavity interactions by modulating the size of ruthenium metallarectangles,” Helvetica Chimica Acta, vol. 93, no. 7, pp. 1313–1328, 2010. View at Publisher · View at Google Scholar · View at Scopus
  76. P. Govindaswamy, J. Furrer, G. Süss-Fink, and B. Therrien, “Encapsulation of triphenylene derivatives in the hexanuclear arene ruthenium metallo-prismatic cage [Ru6(p-PriC6H4Me)6(tpt)2(dhbq)3]6+ (tpt = 2,4,6-tri(pyridin-4-yl)-1,3,5-triazine, dhbq = 2,5-dihydroxy-1,4-benzoquinonato),” Zeitschrift für Anorganische und Allgemeine Chemie, vol. 634, no. 8, pp. 1349–1352, 2008. View at Publisher · View at Google Scholar
  77. J. Mattsson, P. Govindaswamy, J. Furrer et al., “Encapsulation of aromatic molecules in hexanuclear arene ruthenium cages: a strategy to build up organometallic carceplex prisms with a dangling arm standing out,” Organometallics, vol. 27, no. 17, pp. 4346–4356, 2008. View at Publisher · View at Google Scholar · View at Scopus
  78. N. P. E. Barry and B. Therrien, “Host-guest chemistry in the hexanuclear (arene)ruthenium metalla-prismatic cage [Ru6(p-cymene)6(tpt)2(dhnq)3]6+,” European Journal of Inorganic Chemistry, vol. 2009, no. 31, pp. 4695–4700, 2009. View at Publisher · View at Google Scholar
  79. J. Freudenreich, N. P. E. Barry, G. Süss-Fink, and B. Therrien, “Permanent encapsulation or host-guest behavior of aromatic molecules in hexanuclear arene ruthenium prisms,” European Journal of Inorganic Chemistry, vol. 2010, no. 16, pp. 2400–2405, 2010. View at Google Scholar
  80. B. Therrien, G. Süss-Fink, P. Govindaswamy, A. K. Renfrew, and P. J. Dyson, “The “complex-in-a-complex” cations [(acac)2MRu6(p-iPrC6H4Me)6(tpt)2(dhbq)3]6+: a trojan horse for cancer cells,” Angewandte Chemie—International Edition, vol. 47, no. 20, pp. 3773–3776, 2008. View at Publisher · View at Google Scholar
  81. J. Mattsson, O. Zava, A. K. Renfrew et al., “Drug delivery of lipophilic pyrenyl derivatives by encapsulation in a water soluble metalla-cage,” Dalton Transactions, vol. 39, no. 35, pp. 8248–8255, 2010. View at Publisher · View at Google Scholar · View at Scopus
  82. N. P. E. Barry, O. Zava, P. J. Dyson, and B. Therrien, “Excellent correlation between drug release and portal size in metalla-cage drug-delivery systems,” Chemistry, vol. 17, no. 35, pp. 9669–9677, 2011. View at Publisher · View at Google Scholar · View at Scopus
  83. K. D. Tew, “Glutathione-associated enzymes in anticancer drug resistance,” Cancer Research, vol. 54, no. 16, pp. 4313–4320, 1994. View at Google Scholar
  84. D. M. Townsend and K. D. Tew, “The role of glutathione-S-transferase in anti-cancer drug resistance,” Oncogene, vol. 22, no. 47, pp. 7369–7375, 2003. View at Publisher · View at Google Scholar · View at Scopus
  85. A. Pitto-Barry, N. P. E. Barry, O. Zava, R. Deschenaux, and B. Therrien, “Encapsulation of pyrene-functionalized poly(benzyl ether) dendrons into a water-soluble organometallic cage,” Chemistry: An Asian Journal, vol. 6, no. 6, pp. 1595–1603, 2011. View at Publisher · View at Google Scholar · View at Scopus
  86. A. Pitto-Barry, N. P. E. Barry, O. Zava, R. Deschenaux, P. J. Dyson, and B. Therrien, “Double targeting of tumours with pyrenyl-modified dendrimers encapsulated in an arene-ruthenium metallaprism,” Chemistry—A European Journal, vol. 17, no. 6, pp. 1966–1971, 2011. View at Publisher · View at Google Scholar · View at Scopus
  87. A. Pitto-Barry, O. Zava, P. J. Dyson, R. Deschenaux, and B. Therrien, “Enhancement of cytotoxicity by combining pyrenyl-dendrimers and arene ruthenium metallacages,” Inorganic Chemistry, vol. 51, no. 13, pp. 7119–7124, 2012. View at Publisher · View at Google Scholar · View at Scopus
  88. B. W. Henderson and T. J. Dougherty, “How does photodynamic therapy work?” Photochemistry and Photobiology, vol. 55, no. 1, pp. 145–157, 1992. View at Publisher · View at Google Scholar · View at Scopus
  89. T. J. Dougherty, C. J. Gomer, B. W. Henderson et al., “Photodynamic therapy,” Journal of the National Cancer Institute, vol. 90, no. 12, pp. 889–905, 1998. View at Publisher · View at Google Scholar · View at Scopus
  90. M. Ferrari, “Cancer nanotechnology: opportunities and challenges,” Nature Reviews Cancer, vol. 5, no. 3, pp. 161–171, 2005. View at Publisher · View at Google Scholar · View at Scopus
  91. J. Freudenreich, C. Dalvit, G. Süss-Fink, and B. Therrien, “Encapsulation of photosensitizers in hexa- and octanuclear organometallic cages: synthesis and characterization of carceplex and host-guest systems in solution,” Organometallics, vol. 32, no. 10, pp. 3018–3033, 2013. View at Publisher · View at Google Scholar · View at Scopus
  92. B. Therrien, “Transporting and shielding photosensitisers by using water-soluble organometallic cages: a new strategy in drug delivery and photodynamic therapy,” Chemistry, vol. 19, no. 26, pp. 8378–8386, 2013. View at Publisher · View at Google Scholar · View at Scopus
  93. F. Schmitt, J. Freudenreich, N. P. E. Barry, L. Juillerat-Jeanneret, G. Süss-Fink, and B. Therrien, “Organometallic cages as vehicles for intracellular release of photosensitizers,” Journal of the American Chemical Society, vol. 134, no. 2, pp. 754–757, 2012. View at Publisher · View at Google Scholar · View at Scopus
  94. L. E. H. Paul, B. Therrien, and J. Furrer, “Investigation of the reactivity between a ruthenium hexacationic prism and biological ligands,” Inorganic Chemistry, vol. 51, no. 2, pp. 1057–1067, 2012. View at Publisher · View at Google Scholar · View at Scopus
  95. L. E. H. Paul, B. Therrien, J. Furrer, and J. Biol, “Interaction of a ruthenium hexacationic prism with amino acids and biological ligands: ESI mass spectrometry and NMR characterisation of the reaction products,” Journal of Biological Inorganic Chemistry, vol. 17, no. 7, pp. 1053–1062, 2012. View at Publisher · View at Google Scholar
  96. M. Hanif, H. Henke, S. M. Meier et al., “Is the reactivity of M(II)-arene complexes of 3-hydroxy-2(1 H)-pyridones to biomolecules the anticancer activity determining parameteŕ,” Inorganic Chemistry, vol. 49, no. 17, pp. 7953–7963, 2010. View at Publisher · View at Google Scholar · View at Scopus
  97. L. E. H. Paul, J. Furrer, and B. Therrien, “Reactions of a cytotoxic hexanuclear arene ruthenium assembly with biological ligands,” Journal of Organometallic Chemistry, vol. 734, pp. 45–52, 2013. View at Publisher · View at Google Scholar · View at Scopus