New platinum and ruthenium complexes - The latest class of potential chemotherapeutic drugs - A review of recent developments in the field

Mini-Reviews in Medicinal Chemistry

Volumn 9, Issue 13, 2009, Pages 1489-1503

  Amin, Amr ^a,c   Buratovich, Michael A ^b  

^a UNITED ARAB EMIRATES UNIVERSITY   (United Arab Emirates)

^b SPRING ARBOR UNIVERSITY   (United States)

^c CAIRO UNIVERSITY   (Egypt)

Author keywords

Apoptosis; BBR3464; Cancer; Chemotherapeutics; Cisplatin; KP1019; Lipoplatin; NAMI A; Picoplatin; RAPTA; Satraplatin

Indexed keywords

ANTINEOPLASTIC METAL COMPLEX; BBR 3464; CARBOPLATIN; CISPLATIN; COPPER; COPPER ION; EPTAPLATIN; INDAZOLIUM TETRACHLOROBIS(INDAZOLE)RUTHENATE; LIPOPLATIN; LOBAPLATIN; MOLYBDENUM; NEDAPLATIN; OXALIPLATIN; PICOPLATIN; PLATINUM; PLATINUM AMMINE CYCLOHEXYLAMINE DICHLORIDE; PROTEIN BCL 2; RUTHENIUM; SATRAPLATIN; TETRACHLOROBIS 1H INDAZOLE RUTHENATE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; CANCER SURVIVAL; CLINICAL TRIAL; DRUG EFFICACY; HUMAN; HYDROLYSIS; NONHUMAN; PROTEIN EXPRESSION; SHORT SURVEY;

ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; NEOPLASMS; PLATINUM COMPOUNDS; RUTHENIUM COMPOUNDS;

EID: 75449099492     PISSN: 13895575     EISSN: None     Source Type: Journal    
DOI: 10.2174/138955709790361566     Document Type: Short Survey

References (212)

1. Rosenberg, B.; VanCamp, L.; Krigas, T. Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode. Nature, 1965, 205, 698-9.
2. Davies, M.S.; Berners-Price, S.J.; Hambley, T.W. Rates of platination of -AG- and -GA- containing double-stranded oligonucleotides: effect of chloride concentration. J. Inorg. Biochem., 2000, 79, 167-72.
3. Zorbas, H.; Keppler, B.K. Cisplatin damage: are DNA repair proteins saviors or traitors to the cell? Chembiochem., 2005, 6, 1157-66.
4. Takahara, P.M.; Rosenzweig, A.C.; Frederick, C.A.; Lippard, S.J. Crystal structure of double-stranded DNA containing the major adduct of the anticancer drug cisplatin. Nature, 1995, 377, 649-52.
5. Huang, H.; Zhu, L.; Reid, B.R.; Drobny, G. P.; Hopkins, P.B. Solution structure of a cisplatin-induced DNA interstrand cross-link. Science, 1996, 270, 1842-5.
6. Fichtinger-Schepman, A.M.; van der Veer, J.L.; den Hartog, J.H.; Lohman, P. H.; Reedijk, J. Adducts of the antitumor drug cisdiamminedichloroplatinum(II) with DNA: formation, identification, and quantitation. Biochemistry, 1985, 24, 707-13.
7. Kelland, L. The resurgence of platinum-based cancer chemotherapy. Nat. Rev. Cancer, 2007, 7, 573-84.
8. Olinski, R.; Briggs, R.C.; Basinger, M.; Jones, M.M. Effectiveness of chemical agents in removing platinum from DNA isolated from cisplatin-treated HL-60 cells. Acta Biochim. Pol., 1992, 39, 327-34.
9. Eastman, A.; Barry, M.A. Interaction of trans- diamminedichloroplatinum(II) with DNA: formation of monofunctional adducts and their reaction with glutathione. Biochemistry, 1987, 26, 3303-7.
10. Vaisman, A.; Lim, S.E.; Patrick, S.M.; Copeland, W.C.; Hinkle, D.C.; Turchi, J.J.; Chaney, S.G. Effect of DNA polymerases and high mobility group protein 1 on the carrier ligand specificity for translesion synthesis past platinum-DNA adducts. Biochemistry, 1999, 38, 11026-39.
11. Reeves, R.; Adair, J.E. Role of high mobility group (HMG) chromatin proteins in DNA repair. DNA Repair, 2005, 4, 926-38.
12. Siddik, Z.H. Cisplatin: mode of cytotoxic action and molecular basis of resistance. Oncogene, 2003, 22, 7265-79.
13. He, Q.; Liang, C. H.; Lippard, S.J. Steroid hormones induce HMG1 overexpression and sensitize breast cancer cells to cisplatin and carboplatin. Proc. Natl. Acad. Sci. U. S. A., 2000, 97, 5768-72.
14. Galan-Moya, E.M.; Hernandez-Losa, J.; Aceves Luquero, C.I.; de la Cruz-Morcillo, M.A.; Ramírez-Castillejo, C,; Callejas-Valera, J.L.; Arriaga, A.; Aranburo, A.F.; Ramón y Cajal, S.; Silvio Gutkind, J.; Sánchez-Prieto, R. c-Abl activates p38 MAPK independently of its tyrosine kinase activity: Implications in cisplatin-based therapy. Int. J. Cancer, 2008, 122, 289-97.
15. Cepeda, V.; Fuertes, M.A.; Castilla, J.; Alonso, C.; Quevedo, C.; Pérez, J.M. Biochemical mechanisms of cisplatin cytotoxicity. Anticancer Agents Med. Chem., 2007, 7, 3-18.
16. Havelka, A.M.; Berndtsson, M.; Olofsson, M.H.; Shoshan, M.C.; Linder, S. Mechanisms of action of DNA-damaging anticancer drugs in treatment of carcinomas: is acute apoptosis an "off-target" effect. Med. Chem., 2007, 7, 1035-9.
17. Fuchs, M.; Hermannstädter, C.; Hutzler, P.; Häcker, G.; Haller, F.; Höfler, H.; Luber, B. Deletion of exon 8 increases cisplatin-induced E-cadherin cleavage. Exp. Cell Res., 2008, 314, 153-63.
18. Pruefer, F.G.; Lizarraga, F.; Maldonado, V.; Melendez-Zajgla, J. Participation of Omi Htra2 serine-protease activity in the apoptosis induced by cisplatin on SW480 colon cancer cells. J. Chemother., 2008, 20, 348-54.
19. Mandic, A.; Hansson, J.; Linder, S.; Shoshan, M.C. Cisplatin induces endoplasmic reticulum stress and nucleus-independent apoptotic signaling. J. Biol. Chem., 2003, 278, 9100-6.
20. Breckenridge, D.G.; Germain, M.; Mathai, J.P.; Nguyen, M.; Shore, G.C. Regulation of apoptosis by endoplasmic reticulum pathways. Oncogene, 2003, 22, 8608-18.
21. Nakagawa, T.; Yuan, J. Cross-talk between two cysteine protease families. Activation of caspase-12 by calpain in apoptosis. J. Cell Biol., 2000, 150, 887-94.
22. Nawrocki, S.T.; Carew, J.S.; Pino, M.S.; Highshaw, R.A.; Dunner, K. Jr.; Huang, P.; Abbruzzese, J.L.; McConkey, D.J. Bortezomib sensitizes pancreatic cancer cells to endoplasmic reticulum stress-mediated apoptosis. Cancer Res., 2005, 65, 11658-66. Erratum in: Cancer Res., 2009, 69, 1695.
23. Cooley, M.E.; Davis, L.E.; DeStefano, M.; Abrahm, J. Cisplatin: a clinical review. Part I - Current uses of cisplatin and administration guidelines. Cancer Nurs., 1994, 17, 173-84.
24. Wong, E.; Giandomenico, C.M. Current status of platinum-based antitumor drugs. Chem. Rev., 1999, 99, 2451-66.
25. Boulikas, T.; Vougiouka, M. Cisplatin and platinum drugs at the molecular level. Oncol. Rep., 2003, 10, 1663-82.
26. Boulikas, T.; Vougiouka, M. Recent clinical trials using cisplatin, carboplatin and their combination chemotherapy drugs. Oncol. Rep., 2004, 11, 559-95.
27. Boulikas, T.; Pantos, A.; Bellis, E.; Christofis, P. Designing platinum compounds in cancer: structures and mechanisms. Cancer Ther., 2007, 5, 537-83.
28. Amin, A.; Hamza, A.; Kambal, A.; Daoud, S. Herbal extracts counteract cisplatin-mediated cell death in rat testis. Asian J. Androl., 2008, 10, 291-7.
29. McKeage, M.J. Comparative adverse effect profiles of platinum drugs. Drug Saf., 1995, 13, 228-44.
30. Lanzi, C.; Perego, P.; Supino, R.; Romanelli, S.; Pensa, T.; Carenini, N.; Viano, I.; Colangelo, D.; Leone, R.; Apostoli, P.; Cassinelli, G.; Gambetta, R.A.; Zunino, F. Decreased drug accumulation and increased tolerance to DNA damage in tumor cells with a low level of cisplatin resistance. Biochem. Pharmacol., 1998, 55, 1247-54.
31. Wang, G.; Reed, E.; Li, Q.Q. Molecular basis of cellular response to cisplatin chemotherapy in non-small cell lung cancer. Oncol. Rep., 2004, 12, 955-65.
32. Hall, M.D.; Okabe, M.; Shen, D.W.; Liang, X.J.; Gottesman, M.M. The role of cellular accumulation in determining sensitivity to platinum-based chemotherapy. Annu. Rev. Pharmacol. Toxicol., 2008; 48, 495-535.
33. Kartalou, M.; Essigmann, J.M. Mechanisms of resistance to cisplatin. Mutat. Res., 2001, 478, 23-43.
34. Eastman, A.; Schulte, N. Enhanced DNA repair as a mechanism of resistance to cis-diamminedichloroplatinum(II). Biochemistry, 1988, 27, 4730-4.
35. Mistry, P.; Kelland, L.R.; Abel, G.; Sidhar S.; Harrap, K.R. The relationships between glutathione, glutathione-S-transferase and cytotoxicity of platinum drugs and melphalan in eight human ovarian carcinoma cell lines. Br. J. Cancer, 1991, 64, 215-20.
36. Kondo, Y.; Kuo, S.M.; Watkins, S.C.; Lazo, J.S. Metallothionein localization and cisplatin resistance in human hormone-independent prostatic tumor cell lines. Cancer Res., 1995, 55, 474-7.
37. Zunino, F.; Perego, P.; Pilotti, S.; Pratesi, G.; Supino, R.; Arcamone, F. Role of apoptotic response in cellular resistance to cytotoxic agents. Pharmacol. Ther., 1997, 76, 177-85.
38. Mow, B.M.F.; Blajeski, A.L.; Chandra, J.; Kaufmann, S.H. Apoptosis and the response to anticancer therapy. Curr. Opin. Oncol., 2001, 13, 453-62.
39. Makin, G.; Dive, C. Apoptosis and cancer chemotherapy. Trends Cell Biol., 2001, 11, S22-6.
40. Perego, P.; Zunino, F.; Carenini, N.; Giuliani, F.; Spinelli, S.; Howell, S.B. Sensitivity to cisplatin and platinum-containing compounds of Schizosaccharomyces pombe rad mutants. Mol. Pharmcol., 1998, 58, 213-9.
41. Tortora, G.; Ciardiello, F. Targeting of epidermal growth factor receptor and protein kinase A: Molecular basis and therapeutic applications. Ann. Oncol., 2000, 11, 777-83.
42. Christen, R.D.; Isonishi, S.; Jones, J.A.; Jekunen, A.P.; Hom, D.K.; Kroning, R.; Gately, D.P.; Thiebaut, F.B.; Los, G.; Howell, S.B. Signaling and drug sensitivity. Cancer Metastasis Rev., 1994, 13, 175-89.
43. Calvert, A.H.; Harland, S.J.; Newell, D.R.; Siddik, Z.H.; Jones, A.C.; McElwain, T.J.; Raju, S.; Wiltshaw, E.; Smith, I.E.; Baker, J.M.; Peckham, M.J.; Harrap, K.R. Early clinical studies with cisdiammine-1,1-cyclobutane dicarboxylate platinum II. Cancer Chemother. Pharmacol., 1982, 9, 140-7.
44. Curt, G.A.; Grygiel, J.J.; Corden, B.J.; Ozols, R.F.; Weiss, R.B.; Tell, D.T.; Myers, C.E.; Collins, J.M. A phase I and pharmacokinetic study of diamminecyclobutane-dicarboxylatoplatinum (NSC 241240). Cancer Res., 1983, 43, 4470-3.
45. Wiltshaw, E. Ovarian trials at the Royal Marsden. Cancer Treat. Rev., 1985, 12 (Suppl. A), 67-71.
46. Connors, T.A.; Jones, M.; Ross, W.C.J.; Braddock, P.D.; Khokhar, A.R.; Tobel, M.L. New platinum complexes with antitumour activity. Chem. Biol. Interact., 1972, 5, 415-424.
47. Burchenal, J.H.; Kalaher, K.; Dew, K.; Lokys, L. Rationale for development of platinum analogs. Cancer Treat. Rep., 1979, 63.
48. Raymond, E.; Chaney, S.G.; Taamma, A.; Cvitkovic, E. Oxaliplatin: a review of preclinical and clinical studies. Ann. Oncol., 1998, 10, 1053-71.
49. Cvitkovic, E. Ongoing and unsaid on oxaliplatin: the hope. Br. J. Cancer, 1998, 77 (Suppl.), 4, 8-11.
50. Dunn, T.A.; Schmoll, H.J.; Grunwald, V.; Bokemeyer, C.; Casper, J. Comparative cytotoxicity of oxaliplatin and cisplatin in non-seminomatous germ cell cancer cell lines. Invest. New Drugs, 1997, 15.
51. Alberts, D.S.; Fanta, P.T.; Running, K.L.; Adair, L.P. Jr.; Garcia, D.J.; Liu-Stevens, R.; Salmon, S.E. In vitro phase II comparison of the cytotoxicity of a novel platinum analog, nedaplatin (254-S), with that of cisplatin and carboplatin against fresh, human ovarian cancers. Cancer Chemother. Pharmacol., 1997, 39, 493-7.
52. McKeage, M.J. Lobaplatin: a new antitumour platinum drug. Expert Opin. Investig. Drugs, 2001, 10, 119-28.
53. Welink, J.; Boven, E.; Vermorken, J.B.; Gall, H.E.; van der Vijgh, W.J. Pharmacokinetics and pharmacodynamics of lobaplatin (D-19466) in patients with advanced solid tumors, including patients with impaired renal of liver function. Clin. Cancer Res., 1999, 5, 2349-58.
54. Sternberg, C.N.; de Mulder, P.; Fossa, S.; Kaye, S.; Roberts, T.; Pawinsky, A.; Daamen, S. Lobaplatin in advanced urothelial tract tumors. The Genitourinary Group of the European Organization for Research and Treatment of Cancer (EORTC). Ann. Oncol., 1997, 8, 695-6.
55. Degardin, M.; Armand, J.P.; Chevallier, B.; Cappelaere, P.; Lentz, M.A.; David, M.; Roché, H. A clinical screening cooperative group phase II evaluation of lobaplatin (ASTA D-19466) in advanced head and neck cancer. Invest. New Drugs, 1995; 13, 253-5.
56. Kim, D.K.; Kim, H.T.; Tai, J.H.; Cho, Y.B.; Kim, T.S.; Kim, K.H.; Park, J.G.; Hong, W.S. Pharmacokinetics and antitumor activity of a new platinum compound,cis-malonato[(4R,5R)-4,5-bis(aminomethyl) -2-isopropyl- 1, 3-dioxolane]platinum(II), as determined by ex vivo pharmacodynamics. Cancer Chemother. Pharmacol., 1995, 37, 1-6.
57. Kim, D.K.; Kim, H.T.; Cho, Y.B.; Tai. J.H.; Ahn, J.S.; Kim, T.S.; Kim, K.H.; Hong, W.S. Antitumor activity of cis -malonato[(4 R ,5 R )-4,5-bis(aminomethy1)-2-isopropyl-1,3-dioxolanelplatinum(II), a new platinum analogue, as an anticancer agent. Cancer Chemother. Pharmacol., 1995, 35, 441-5.
58. Kim, N.K.; Kim, T.Y.; Shin, S.G.; Park, Y.I.; Lee, J.A.; Cho, Y.B.; Kim, K.H.; Kim, D.K.; Heo, D.S.; Bang, Y.J. A Phase I study of cis-malonato[(4R,5R)- 4,5-bis(aminomethyl)-1,3-dioxolane] platinum(II) in patients with advanced malignancies. Cancer, 2001, 91, 1549-56.
59. Zang, D.Y.; Lee, K.H.; Lee, J.S.; Lee, J.H.; Kim, W.K.; Kim, S.H.; Kim, W.D.; Kim, D.S.; Kim, J.H.; Kim, B.S.; Cho, Y.B.; Kim, D.K.; Kim, K.H. Phase II trial of a novel platinum analog, SKI 2053R, in patients with previously untreated extensive-stage small-cell lung cancer. Am. J. Clin. Oncol., 1999, 22, 495-8.
60. Kim, N.K.; Im, S.A.; Kim, D.W.; Lee, M.H.; Jung, C.W.; Cho, E.K.; Lee, J.T.; Ahn, J.S.; Heo, D.S.; Bang, Y.J. Phase II clinical trial of SKI-2053R, a new platinum analog, in the treatment of patients with advanced gastric adenocarcinoma. Cancer, 1999, 86, 1109-15.
61. Choi, C.H.; Cha, Y.J.; An, C.S.; Kim, K.J.; Kim, K.C.; Moon, S.P.; Lee, Z.H.; Min, Y.D. Molecular mechanisms of heptaplatin effective against cisplatin-resistant cancer cell lines: less involvement of metallothionein. Cancer Cell Int., 2004, 4, 6.
62. Dyson, P.J.; Sava, G. Metal-based antitumour drugs in the post genomic era. Dalton Trans., 2006, 28, 1929-33.
63. Bruijnincx, P.C.; Sadler, P.J. New trends for metal complexes with anticancer activity. Curr. Opin. Chem. Biol,. 2008, 12, 197-206.
64. Jakupec, M.A.; Galanski, M.; Arion, V.B.; Hartinger, C.G.; Keppler, B.K. Antitumour metal compounds: more than theme and variations. Dalton Trans., 2008, 14, 183-94.
65. Galanski, M.; Jakupec, M.A.; Keppler, B.K. Update of the preclinical situation of anticancer platinum complexes: novel design strategies and innovative analytical approaches. Curr. Med. Chem., 2005, 12, 2075-94.
66. Wheate, N.J.; Collins, J.G. Multi-nuclear platinum drugs: a new paradigm in chemotherapy. Curr. Med. Chem. Anticancer Agents, 2005, 5, 267-79.
67. Perego, P.; Gatti, L.; Righetti, S.C.; Beretta, G.L.; Carenini, N.; Corna, E.; Dal Bo, L.; Tinelli, S.; Colangelo, D.; Leone, R.; Apostoli, P.; Lombardi, L.; Beggiolin, G.; Piazzoni, L.; Zunino, F. Development of resistance to a trinuclear platinum complex in ovarian carcinoma cells. Int. J. Cancer, 2003, 105, 617-24.
68. Riccardi, A.; Meco, D.; Ferlini, C.; Servidei, T.; Carelli, G.; Segni, G.; Manzotti, C.; Riccardi, R. In vitro and in vivo antitumor activity of the novel trinuclear platinum complex BBR 3464 in neuroblastoma. Cancer Chemother. Pharmacol., 2001, 47, 498-504.
69. Colella, G.; Pennati, M.; Bearzatto, A.; Leone, R.; Colangelo, D.; Manzotti, C.; Daidone, M.G.; Zaffaroni, N. Activity of a trinuclear platinum complex in human ovarian cancer cell lines sensitive and resistant to cisplatin: cytotoxicity and induction and gene-specific repair of DNA lesions. Br. J. Cancer, 2001, 84, 1387-90.
70. Servidei, T.; Ferlini, C.; Riccardi, A.; Meco, D.; Scambia, G.; Segni, G.; Manzotti, C.; Riccardi, R. The novel trinuclear platinum complex BBR3464 induces a cellular response different from cisplatin. Eur. J. Cancer, 2001, 37, 930-8.
71. Perego, P.; Gatti, L.; Caserini, C.; Supino, R.; Colangelo, D.; Leone, R.; Spinelli, S.; Farrell, N.; Zunino, F. The cellular basis of the efficacy of the trinuclear platinum complex BBR 3464 against cisplatin-resistant cells. J. Inorg. Biochem. 1999, 77, 59-64.
72. Roberts, J.D.; Peroutka, J.; Farrell, N. Cellular pharmacology of polynuclear platinum anti-cancer agents. J. Inorg. Biochem., 1999, 77, 51-7.
73. Perego, P.; Caserini, C.; Gatti, L.; Carenini, N.; Romanelli, S.; Supino, R.; Colangelo, D.; Viano, I.; Leone, R.; Spinelli, S.; Pezzoni, G.; Manzotti, C.; Farrell, N.; Zunino, F. A novel trinuclear platinum complex overcomes cisplatin resistance in an osteosarcoma cell system. Mol Pharmacol. 1999, 55, 528-34. Erratum in: Mol. Pharmacol., 1999, 55, 1108.
74. Di Blasi, P.; Bernareggi, A.; Beggiolin, G.; Piazzoni, L.; Menta, E.; Formento, M.L. Cytotoxicity, cellular uptake and DNA binding of the novel trinuclear platinun complex BBR 3464 in sensitive and cisplatin resistant murine leukemia cells. Anticancer Res., 1998, 18, 3113-7.
75. Hegmans, A.; Berners-Price, S.J.; Davies, M.S.; Thomas, D.S.; Humphreys, A.S.; Farrell, N. 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. J. Am. Chem. Soc., 2004, 126, 2166-80.
76. Brabec, V.; Kaspárková, J.; Vrána, O.; Nováková, O.; Cox, J.W., Qu, Y.; Farrell, N. DNA modifications by a novel bifunctional trinuclear platinum phase I anticancer agent. Biochemistry, 1999, 38, 6781-99.
77. McGregor, T.D.; Hegmans, A.; Kaspárková, J.; Neplechová, K.; Nováková, O.; Penazová, H.; Vrána, O.; Brabec, V.; Farrell, N. A comparison of DNA binding profiles of dinuclear platinum compounds with polyamine linkers and the trinuclear platinum phase II clinical agent BBR3464. J. Biol. Inorg. Chem., 2002, 7, 397-404.
78. McGregor, T.D.; Bousfield, W.; Qu, Y.; Farrell, N. Circular dichroism study of the irreversibility of conformational changes induced by polyamine-linked dinuclear platinum compounds. J. Inorg. Biochem., 2002, 91, 212-9.
79. Qu, Y.; Scarsdale, N.J.; Tran, M.C.; Farrell, N. Comparison of structural effects in 1,4 DNA-DNA interstrand cross-links formed by dinuclear and trinuclear platinum complexes. J. Inorg. Biochem., 2004, 98, 1585-90.
80. Qu, Y.; Scarsdale, N.J.; Tran, M.C.; Farrell, N.P. 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. J. Biol. Inorg. Chem,. 2003, 8, 19-28.
81. Zehnulova, J.; Kasparkova, J.; Farrell, N.; Brabec, V. Conformation, recognition by high mobility group domain proteins, and nucleotide excision repair of DNA intrastrand cross-links of novel antitumor trinuclear platinum complex BBR3464. J. Biol. Chem., 2001, 276, 22191-9.
82. Kasparkova, J.; Zehnulova, J.; Farrell, N.; Brabec, V. DNA interstrand cross-links of the novel antitumor trinuclear platinum complex BBR3464. Conformation, recognition by high mobility group domain proteins, and nucleotide excision repair. J. Biol. Chem., 2002, 277, 48076-86.
83. Liu, Q.; Qu, Y.; Van Antwerpen, R.; Farrell, N. Mechanism of the membrane interaction of polynuclear platinum anticancer agents. Implications for cellular uptake. Biochemistry, 2006, 45, 4248-56.
84. 4+ influenced by copper homeostasis. Biochem. Pharmacol., 2007, 73, 1270-9.
85. O'Connor, P.M.; Jackman, J.; Bae, I.; Myers, T.G.; Fan, S.; Mutoh, M.; Scudiero, D.A.; Monks, A.; Sausville, E.A.; Weinstein, J.N.; Friend, S.; Fornace, A.J. Jr.; Kohn, K.W. Characterization of the p53 tumor suppressor pathway in cell lines of the National Cancer Institute anticancer drug screen and correlations with the growth-inhibitory potency of 123 anticancer agents. Cancer Res., 1997, 57, 4285-300.
86. Servidei, T.; Ferlini, C.; Riccardi, A.; Meco, D.; Scambia, G.; Segni, G.; Manzotti, C.; Riccardi, R. The novel trinuclear platinum complex BBR3464 induces a cellular response different from cisplatin. Eur. J. Cancer, 2001, 37, 930-8.
87. Pratesi, G.; Perego, P.; Polizzi, D.; Righetti, S.C.; Supino, R.; Caserini, C.; Manzotti, C.; Giuliani, F.C.; Pezzoni, G.; Tognella, S.; Spinelli, S.; Farrell, N.; Zunino, F. A novel charged trinuclear platinum complex effective against cisplatin-resistant tumours: hypersensitivity of p53-mutant human tumour xenografts. Br. J. Cancer, 1999, 80, 1912-9.
88. Orlandi, L.; Colella, G.; Bearzatto, A.; Abolafio, G.; Manzotti, C.; Daidone, M.; Zafferoni, N. Effects of a novel trinuclear platinum complex in cisplatin-sensitive and cisplatin-resistant human ovarian cancer cell lines: interference with cell cycle progression and induction of apoptosis. Eur. J. Cancer, 2001, 37, 649-59.
89. Harris, C.C.; Hollstein, M. Clinical implications of the p53 tumor-suppressor gene. N. Engl. J. Med., 1993, 329, 1318-27.
90. Sessa, C.; Capri, G.; Gianni, L.; Peccatori, F.; Grasselli, G.; Bauer, J.; Zucchetti, M.; Viganò, L.; Gatti, A.; Minoia, C.; Liati, P.; Van den Bosch, S.; Bernareggi, A.; Camboni, G.; Marsoni, S. Clinical and pharmacological phase I study with accelerated titration design of a daily times five schedule of BBR3464, a novel cationic triplatinum complex. Ann Oncol., 2000, 11, 977-83.
91. Hensing, T.A.; Hanna, N.H.; Gillenwater, H.H.; Gabriella Camboni, M.; Allievi, C.; Socinski, M.A. Phase II study of BBR 3464 as treatment in patients with sensitive or refractory small cell lung cancer. Anticancer Drugs, 2006, 17, 697-704.
92. Jodrell, D.I.; Evans, T.R.; Steward, W.; Cameron, D.; Prendiville, J.; Aschele, C.; Noberasco, C.; Lind, M.; Carmichael, J.; Dobbs, N.; Camboni, G.; Gatti, B.; De Braud, F. Phase II studies of BBR3464, a novel tri-nuclear platinum complex, in patients with gastric or gastro-oesophageal adenocarcinoma. Eur. J. Cancer, 2004, 40, 1872-7.
93. Mitchell, C.; Kabolizadeh, P.; Ryan, J.; Roberts, J.D.; Yacoub, A.; Curiel, D.T.; Fisher, P.B.; Hagan, M.P.; Farrell, N.P.; Grant, S.; Dent, P. Low-dose BBR3610 toxicity in colon cancer cells is p53-independent and enhanced by inhibition of epidermal growth factor receptor (ERBB1)-phosphatidyl inositol 3 kinase signaling. Mol. Pharmacol., 2007, 72, 704-14.
94. Kelland, L. Broadening the clinical use of platinum drug-based chemotherapy with new analogues. Satraplatin and picoplatin. Opin. Investig. Drugs, 2007, 16, 1009-21.
95. Stewart, D.J. Mechanisms of resistance to cisplatin and carboplatin. Crit. Rev. Oncol. Hematol., 2007, 63, 12-31.
96. Judson, I.; Kelland, L.R. New developments and approaches in the platinum arena. Drugs, 2000, 59(Suppl 4), 29-36.
97. Holford, J.; Raynaud, F.; Murrer, B.A.; Grimaldi, K.; Hartley, J.A.; Abrams, M.; Kelland, L.R. Chemical, biochemical and pharmacological activity of the novel sterically hindered platinum coordination complex, cis-[amminedichloro(2-methylpyridine)] platinum(II) (AMD473) Anticancer Drug Des., 1998, 13, 1-18.
98. Piccart, M.J.; Lamb, H.; Vermorken, J.B. Current and future potential roles of the platinum drugs in the treatment of ovarian cancer. Ann Oncol., 2001, 12, 1195-203.
99. Rogers, P.; Boxall, F.E.; Allot, C.P.; Stephens, T.C.; Kelland, L.R. Sequence-dependent synergism between the new generation platinum agent ZD0473 and paclitaxel in cisplatin-sensitive and resistant human ovarian carcinoma cell lines. Eur. J. Cancer, 2002, 38, 1653-60.
100. Beale, P.; Judson, I.; O'Donnell, A.; Trigo, J.; Rees, C.; Raynaud, F.; Turner, A.; Simmons, L.; Etterley, L. A Phase I clinical and pharmacological study of cis-diamminedichloro(2-methylpyridine) platinum II (AMD473). Br. J. Cancer, 2003, 88, 1128-34.
101. Twelves, C.; Reck, M.; Anthoney, A.; Gatzemeier; U.; Kaye, S. phase I study of ZD0473 combined with paclitaxel for the treatment of solid malignancies. Cancer Chemother. Pharmacol., 2003, 52, 277-81.
102. Flaherty, K.T.; Stevenson, J.P.; Redlinger, M. A phase I, dose escalation trial of ZD0473, a novel platinum analogue, in combination with gemcitabine. Cancer Chemother. Pharmacol., 2004, 53, 404-8.
103. Kanzawa, F.; Akiyama, Y.; Saijo, N.; Nishio, K. In vitro effects combinations of cis-amminedichloro (2-methylpyridine) platinum (II) (ZD0473) with other novel anticancer drugs on the growth SBC-3, a human small cell lung cancer cell line. Lung Cancer. 2003, 40, 325-32.
104. Douillard, J.Y.; Schiller, J. ZD0473 combined with other chemotherapeutic agents for the treatment of solid malignancies. Eur. J. Cancer, 2002, 38, (Suppl. 8), S25-31.
105. Gore, M.E.; Atkinson, R.J.; Thomas, H.; Cure, H.; Rischin, D.; Beale, P.; Bougnoux, P.; Dirix, L.; Smit, W.M. Results of ZD0473 in platinum-pretreated ovarian cancer: analysis according to platinum free interval. Eur. J. Cancer, 2002, 38 (Suppl. 8), S7-12.
106. Gore, M.E.; Atkinson, R.J.; Thomas, H.; Cure, H.; Rischin, D.; Beale, P.; Bougnoux, P.; Dirix, L.; Smit, W.M. A phase II trial of ZD0473 in platinum-pretreated ovarian cancer. Eur. J. Cancer, 2002, 38, 2416-20.
107. Treat, J.; Schiller, J.; Quoix, E.; Mauer, A.; Edelman, M.; Modiano, M.; Bonomi, P.; Ramlau, R.; Lemarie, E. ZD0473 treatment in lung cancer: an overview of the clinical trial results. Eur. J. Cancer, 2002, 38 (Suppl. 8), S13-8.
108. Kelland, L.R.; Abel, G.; McKeage, M.J.; Jones, M.; Goddard, P.M.; Valenti, M.; Murrer, B.A.; Harrap, K.R. Preclinical antitumor evaluation of bis-acetato-ammine-dichloro-cyclohexylamine platinum(IV): an orally active platinum drug. Cancer Res., 1993, 53, 2581-6.
109. Sharp, S.Y.; Rogers, P.M.; Kelland, L.R. Transport of cisplatin and bis-acetato-ammine-dichlorocyclohexylamine Platinum(IV) (JM216) in human ovarian carcinoma cell lines: identification of a plasma membrane protein associated with cisplatin resistance. Clin. Cancer Res., 1995, 1, 981-9.
110. Samimi, G.; Howell, S.B. Modulation of the cellular pharmacology of JM118, the major metabolite of satraplatin, by copper influx and efflux transporters. Cancer Chemother. Pharmacol., 2006, 57, 781-8.
111. Wosikowski, K.; Lamphere, L.; Unteregger, G.; Jung, V.; Kaplan, F.; Xu, J.P.; Rattel, B.; Caligiuri, M. Preclinical antitumor activity of the oral platinum analog satraplatin. Cancer Chemother Pharmacol., 2007, 60, 589-600.
112. McKeage, M.J.; Mistry, P.; Ward, P.; Boxall, F.E.; Loh, S.; O'Neill, C.; Ellis, P.; Kelland, L.R.; Morgan, S.E.; Murrer, B.; Santabarbara, P.; Harrap, K.R.; Judson, I.R. A phase I and pharmacology study of an oral platinum complex, JM216: dose-dependent pharmacokinetics with single-dose administration. Cancer Chemother Pharmacol., 1995, 36, 451-8.
113. Sessa, C.; Minoia, C.; Ronchi, A.; Zucchetti, M.; Bauer, J.; Borner, M.; de Jong, J.; Pagani, O.; Renard, J.; Weil, C.; D'Incalci, M. Phase I clinical and pharmacokinetic study of the oral platinum analogue JM216 given daily for 14 days. Ann Oncol., 1998, 9, 1315-22.
114. Lebwohl, D.; Canetta, R. Clinical development of platinum complexes in cancer therapy: an historical perspective and an update. Eur. J. Cancer, 1998, 34, 1522-34.
115. Latif, T.; Wood, L.; Connell, C.; Smith, D.C.; Vaughn, D.; Lebwohl, D.; Peereboom, D. Phase II study of oral bis (aceto) ammine dichloro (cyclohexamine) platinum (IV) (JM-216, BMS-182751) given daily x 5 in hormone refractory prostate cancer (HRPC). Invest. New Drugs, 2005, 23, 79-84.
116. Sternberg, C.N.; Whelan, P.; Hetherington, J.; Paluchowska, B.; Slee, P.H.; Vekemans, K.; Van Erps, P.; Theodore, C.; Koriakine, O.; Oliver, T.; Lebwohl, D.; Debois, M.; Zurlo, A.; Collette, L.; Genitourinary Tract Group of the EORTC. Phase III trial of satraplatin, an oral platinum plus prednisone vs. prednisone alone in patients with hormone-refractory prostate cancer. Oncology, 2005, 68, 2-9.
117. McKeage, M.J. Satraplatin in hormone-refractory prostate cancer and other tumour types: pharmacological properties and clinical evaluation. Drugs, 2007, 67, 859-69.
118. A summary of the results of the phase III SPARC trial is available at http://www.prostate-cancer.org/advocacy/SatraplatinFDA-Review. html. Accessed on June 4, 2009.
119. Choy, H.; Park, C.; Yao, M. Current status and future prospects for satraplatin, an oral platinum analogue. Clin. Cancer Res., 2008, 14, 1633-8.
120. Boulikas, T. Low toxicity and anticancer activity of a novel liposomal cisplatin (Lipoplatin) in mouse xenografts. Oncol. Rep. 2004, 12, 3-12.
121. Boulikas, T.; Stathopoulos, G.P.; Volakakis, N.; Vougiouka, M. Systemic Lipoplatin infusion results in preferential tumor uptake in human studies. Anticancer Res., 2005, 25, 3031-9.
122. Stathopoulos, G.P.; Boulikas, T.; Vougiouka, M.; Deliconstantinos, G.; Rigatos, S.; Darli, E.; Vilotou, V.; Stathopoulos, J. G. Pharmacokinetics and adverse reactions of a new liposomal cisplatin (Lipoplatin): phase I study. Oncol. Rep., 2005, 13, 589-95.
123. Stathopoulos, G.P.; Boulikas, T.; Vougiouka, M.; Rigatos, S.; Stathopoulos, J. G. Liposomal cisplatin combined with gemcitabine in pretreated advanced pancreatic cancer patients: a phase I-II study. Oncol. Rep., 2006, 15, 1201-4.
124. Yamashita, Y.; Krauze, M.T.; Kawaguchi, T.; Noble, C.O.; Drummond, D.C.; Park, J.W.; Bankiewicz, K.S. Convection-enhanced delivery of a topoisomerase I inhibitor (nanoliposomal topotecan) and a topoisomerase II inhibitor (pegylated liposomal doxorubicin) in intracranial brain tumor xenografts. Neuro Oncol., 2007, 9, 20-8.
125. Stathopoulos, G.P.; Boulikas, T.; Kourvetaris, A.; Stathopoulos, J. Liposomal oxaliplatin in the treatment of advanced cancer: a phase I study. Anticancer Res., 2006, 26, 1489-93.
126. Nicoletto, M.O.; Falci, C.; Pianalto, D.; Artioli, G.; Azzoni, P.; De Masi, G.; Ferrazzi, E.; Perin, A.; Donach, M.; Zoli, W. Phase II study of pegylated liposomal doxorubicin and oxaliplatin in relapsed advanced ovarian cancer. Gynecol. Oncol., 2006, 100, 318-23.
127. Recchia, F.; Saggio, G.; Amiconi, G.; Di Blasio, A.; Cesta, A.; Candeloro, G.; Carta, G.; Necozione, S.; Mantovani, G.; Rea, S. A multicenter phase II study of pegylated liposomal doxorubicin and oxaliplatin in recurrent ovarian cancer. Gynecol. Oncol., 2007, 106, 164-9.
128. Valerio, M.R., Tagliaferri, P.; Raspagliesi, F.; Fulfaro, F.; Badalamenti, G.; Arcara, C.; Cicero, G.; Russo, A.; Venuta, S.; Guarneri, G.; Gebbia, N. A phase II study of pegylated liposomal doxorubicin oxaliplatin and cyclophosphamide as second-line treatment in relapsed ovarian carcinoma. Int. J. Gynecol. Cancer, 2006, 16 (Suppl. 1), 79-85.
129. Dragovich, T.; Mendelson, D.; Kurtin, S.; Richardson, K.; Von Hoff, D.; Hoos, A. A Phase 2 trial of the liposomal DACH platinum L-NDDP in patients with therapy-refractory advanced colorectal cancer. Cancer Chemother. Pharmacol., 2006, 58, 759-64.
130. Anghileri, L.J. The in vivo inhibition of tumor growth by ruthenium red: its relationship with the metabolism of calcium in the tumor. Z. Krebsforsch. Klin. Onkol. Cancer Res. Clin. Oncol., 1975, 83, 213-7.
131. (a) Sava, G.; Alessio, E.; Bergamo, A.; Mestroni, G. In Metallo-pharmaceuticals I: DNA Interactions; Michael J. Clarke, Peter J. Sadler, Eds.; Springer: Dublin, 1999; Vol. 1, pp. 143-169.
132. (b) Clarke, M.J. In Metal Ions in Biological Systems; Helmut Sigel, Ed.; Marcel Dekker, Inc.: New York, 1980; pp. 231-83.
133. Clarke, M.J.; Taube, H. Pentaammineruthenium-guanine complexes. J. Am. Chem. Soc., 1974, 96, 5413-19.
134. Bruijnincx, P.C.A.; Sadler, P.J. New trends for metal complexes with anticancer activity. Curr. Opin. Chem. Biol., 2008, 12, 197-206.
135. Ronconi, L.; Sadler, P.J. Using coordination chemistry to design new medicines. Coord. Chem. Rev., 2007, 251, 1633-48.
136. Bacac, M.; Hotze, A.; Schilden, K.; Haasnoot, J.; Pacor, S.; Alessio, E.; Sava, G.; Reedijk, J. The hydrolysis of the anti-cancer ruthenium complex NAMI-A affects its DNA binding and antimetastatic activity: an NMR evaluation. J. Inorg. Biochem., 2004, 98, 402-12.
137. Chen, H.; Parkinson, J.A.; Morris, R.E.; Sadler, P.J. Highly selective binding of organometallic ruthenium ethylenediamine complexes to nucleic acids: novel recognition mechanisms. J. Am. Chem. Soc., 2003, 125, 173-86.
138. Melchart, M.; Habtemariam, A.; Novakova, O.; Moggach, S.A.; Fabbiani, F.P.A.; Parsons, S.; Brabec, V.; Sadler, P.J. Bifunctional amine-tethered ruthenium(II) arene complexes form monofunctional adducts on DNA. Inorg. Chem., 2007, 46, 8950-62.
139. Peacock, A.F.A.; Melchart, M.; Deeth, R.J.; Habtemariam, A.; Parsons, S.; Sadler, P J. Osmium(II) and ruthenium(II) arene maltolato complexes: rapid hydrolysis and nucleobase binding. Chem. Eur. J., 2007, 13, 2601-13.
140. Peacock, A.F.A.; Parsons, S.; Sadler, P.J. Tuning the hydrolytic aqueous chemistry of osmium arene complexes with N,O-chelating ligands to achieve cancer cell cytotoxicity. J. Am. Chem. Soc., 2007, 129, 3348-57.
141. Morris, R.E.; Aird, R.E.; Murdoch Pdel, S.; Chen, H.; Cummings, J.; Hughes, N.D.; Parsons, S.; Parkin, A.; Boyd, G.; Jodrell, D.I.; Sadler, P.J. Inhibition of cancer cell growth by ruthenium(II) arene complexes. J. Med. Chem., 2001, 44, 3616-21.
142. Bergamo, A.; Masi, A.; Dyson, P.J.; Sava, G. Modulation of the metastatic progression of breast cancer with an organometallic ruthenium compound. Int. J. Oncol., 2008, 33, 1281-9.
143. Scolaro, C.; Bergamo, A.; Brescacin, L.; Delfino, R.; Cocchietta, M.; Laurenczy, G.; Geldbach, T.J.; Sava, G.; Dyson, P.J. In vitro and in vivo evaluation of ruthenium(II)-arene PTA complexes. J. Med. Chem., 2005, 48, 4161-71.
144. 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. Chem. Commun., 2001, 15, 1396-7.
145. Scolaro, C.; Geldbach, T.J.; Rochat, S.; Dorcier, A.; Gossens, C.; Bergamo, A.; Cocchietto, M.; Tavernelli, I.; Sava, G.; Rothlisberger, U.; Dyson, P.J. Influence of hydrogen-bonding Substituents on the Cytotoxicity of RAPTA Compounds. Organometallics, 2006, 25, 756-765.
146. Dorcier, A.; Dyson, P.J.; Gossens, C.; Rothlisberger, U.; Scopelliti, R.; Tavernelli, I. Binding of organometallic ruthenium(II) and osmium(II) complexes to an oligonucleotide: a combined mass spectrometric and theoretical study. Organometallics, 2005, 24, 2114-2123.
147. Chatterjee, S.; Kundu, S.; Bhattacharyya, A.; Hartinger, C.G.; Dyson, P.J. The ruthenium(II)-arene compound RAPTA-C induces apoptosis in EAC cells through mitochondrial and p53-JNK pathways. J. Biol. Inorg. Chem., 2008, 13, 1149-55.
148. Casini, A.; Gabbiani, C.; Sorrentino, F.; Rigobello, M.P.; Bindoli, A.; Geldbach, T.J.; Marrone, A.; Re. N.; Hartinger, C.G.; Dyson, P.J.; Messori, L. Emerging protein targets for anticancer metallodrugs: inhibition of thioredoxin reductase and cathepsin B by antitumor ruthenium(II)-arene compounds. J. Med. Chem., 2008, 51, 6773-81.
149. Mohamed, M.M.; Sloane, B.F. Cysteine cathepsins: multifunctional enzymes in cancer. Nat. Rev. Cancer, 2006, 6, 764-75.
150. Scolaro, C.; Hartinger, C.G.; Allardyce, C.S.; Keppler, B.K.; Dyson, P.J. Hydrolysis study of the bifunctional antitumour compound RAPTA-C, [Ru(eta6-p-cymene)Cl2(pta)]. J. Inorg. Biochem., 2008, 102, 1743-8.
151. Ang, W.H.; Juillerat-Jeannerat, L.; Dyson, P.J. Development of organometallic ruthenium-arene anticancer drugs that resist hydrolysis. Inorg. Chem., 2006, 45, 9006-13.
152. Lipponer, K.-G.; Vogel, E.; Keppler, B.K. Synthesis, Characterization and Solution Chemistry of trans-Indazoliumtetrachlorobis(Indazole) Ruthenate(III), a New Anticancer Ruthenium Complex. IR, UV, NMR, HPLC Investigations and Antitumor Activity. Crystal Structures of trans-1-Methyl-Indazoliumtetrachlorobis-(1-Methylindazole)Ruthenate(III) and its hydrolysis product trans-monoaquatrichlorobis-(1-methylindazole)- ruthenate(III). Metal-Based Drugs, 1996, 3, 243-60.
153. Küng, A.; Pieper, T.; Wissiack, R.; Rosenberg, E.; Keppler, B.K. Hydrolysis of the tumor-inhibiting ruthenium(III) complexes HIm trans-[RuCl4(im)2] and HInd trans-[RuCl4(ind)2] investigated by means of HPCE and HPLC-MS. J. Biol. Inorg. Chem., 2001, 6, 292-9.
154. Hartinger, C.G.; Jakupec, M. A.; Zorbas-Seifried, S.; Groessl, M.; Egger, A.; Berger, W.; Zorbas, H.; Dyson, P.J.; Keppler, B.K. KP1019, a new redox-active anticancer agent - preclinical development and results of a clinical phase I study in tumor patients. Chem. Biodivers., 2008, 5, 2140-55.
155. Kratz, F.; Messori, L. Spectral characterization of ruthenium (III) transferrin. J. Inorg. Biochem., 1993, 49, 79-82.
156. Messori, L.; Kratz, F.; Alessio, E. The interaction of the antitumor complexes Na[trans-RuCl(4) (DMSO)(Im)] and Na[trans-RuCl-(4)(DMSO) (Ind)] with apotransferrin: a spectroscopic study. Metal-Based Drugs, 1996, 3, 1-9.
157. Messori, L.; Vilchez, F.G.; Vilaplana, R.; Piccioli, F.; Alessio, E.; Keppler, B. Binding of antitumor ruthenium(III) complexes to plasma proteins. Metal-Based Drugs, 2000, 7, 335-42.
158. Pongratz, M.; Schluga, P.; Jakupec, M.A.; Arion, V.B.; Hartinger, C.G.; Allmaier, G.; Keppler, B.K. Transferrin binding and transferrin-mediated cellular uptake of the ruthenium coordination compound KP1019, studied by means of AAS, ESI-MS and CD spectroscopy. J. Anal. At. Spectr., 2004, 19, 46-51.
159. Trynda-Lemiesz, L.; Karaczyn, A.; Keppler, B.K.; Koz owski, H. Studies on the interactions between human serum albumin and trans-indazolium (bisindazole) tetrachlororuthenate(III). J. Inorg. Biochem., 2000, 78, 341-6.
160. Kratz, F.; Hartmann, M.; Keppler, B.; Messori, L. The binding properties of two antitumor ruthenium(III) complexes to apotransferrin. J. Biol. Chem., 1994, 269, 2581-8.
161. Küng, A.; Pieper, T.; Keppler, B.K. Investigations into the interaction between tumor-inhibiting ruthenium(III) complexes and nucleotides by capillary electrophoresis. J. Chromatogr. B, 2001, 759, 81-9.
162. Frühauf, S.; Zeller, W.J. New platinum, titanium, and ruthenium complexes with different patterns of DNA damage in rat ovarian tumor cells. Cancer Res., 1991, 51, 2943-8.
163. Malina, J.; Novakova, O.; Keppler, B.K.; Alessio, E.; Brabec, V. Biophysical analysis of natural, double-helical DNA modified by anticancer heterocyclic complexes of ruthenium(III) in cell-free media. J. Biol. Inorg. Chem., 2001, 6, 435-45.
164. Hartinger, C.G.; Zorbas-Seifried, S.; Jakupec, M.A.; Kynast, B.; Zorbas, H.; Keppler, B.K. From bench to bedside - preclinical and early clinical development of the anticancer agent indazolium trans-[tetrachlorobis(1H- indazole)ruthenate(III)] (KP1019 or FFC14A). J. Inorg. Biochem., 2006, 100, 891-904.
165. Kapitza, S.; Pongratz, M.; Jakupec, M.A.; Heffeter, P.; Berger, W.; Lackinger, L.; Keppler, B.K.; Marian, B. Heterocyclic complexes of ruthenium(III) induce apoptosis in colorectal carcinoma cells. J. Cancer Res. Clin. Oncol., 2005, 131, 101-10.
166. Heffeter, P.; Pongratz, M.; Steiner, E.; Chiba, P.; Jakupec, M.A.; Elbling, L.; Marian, B.; Kcrner, W.; Sevelda, F.; Micksche, M.; Keppler, B.K.; Berger, W. Intrinsic and acquired forms of resistance against the anticancer ruthenium compound KP1019 [indazoliumtrans-[tetrachlorobis(1H-indazole)ruthenate (III)] (FFC14A). J. Pharmacol. Exp. Ther., 2005, 312, 281-9.
167. Kreuser, E.D.; Keppler, B.K.; Berdel, W.E.; Piest, A.; Thiel, E. Synergistic antitumor interactions between newly synthesized ruthenium complexes and cytokines in human colon carcinoma cell lines. Semin. Oncol., 1992, 19, 73-81.
168. Keppler, B.K.; Lipponer, K.G.; Stenzel, B.; Kratz, F. In Metal Complexes in Cancer Chemotherapy; Keppler, B.K. Ed.; Wiley-VCH Verlag GmbH: Weinheim, 1993, pp. 187-220.
169. Galanski, M.; Arion, V.B.; Jakupec, M.A.; Keppler, B.K. Recent developments in the field of tumor-inhibiting metal complexes. Curr. Pharm. Des., 2003, 9, 2078-89.
170. Berger, M.R.; Garzon, F.T.; Keppler, B.K.; Schmähl, D. Efficacy of new ruthenium complexes against chemically induced autochthonous colorectal carcinoma in rats. Anticancer Res., 1989, 9, 761-5.
171. Jakupec, M.A.; Arion, V.B.; Kapitza, S.; Reisner, E.; Eichinger, A.; Pongratz, M.; Marian, B.; Graf von Keyserlingk, N.; Keppler, B.K. KP1019 (FFC14A) from bench to bedside: preclinical and early clinical development - an overview. Int. J. Clin. Pharmacol. Ther., 2005, 43, 595-6.
172. Pieper, T.; Borsky, K.; Keppler, B.K. In Metallopharmaceuticals II: Diagnosis and Therapy (Topics in Biological Inorganic Chemistry); M.J. Clarke, E. Alessio, P.J. Sadler, Eds.; Springer: London, 1999; Vol 1, pp. 171-199.
173. Keppler, B.K.; Henn, M.; Juhl, U.M.; Berger, M.R.; Niebl, R.; Wagner, F.E. New ruthenium complexes for the treatment of cancer. Prog. Clin. Biochem. Med., 1989, 10, 41-69.
174. Hartmann, M.; Keppler, B.K. Inorganic Anticancer Agents: Their Chemistry and Antitumor Properties. Comm. Inorg. Chem., 1995, 16, 339-72.
175. Sava, G.; Bergamo, A. Ruthenium-based compounds and tumour growth control (review). Int. J. Oncol., 2000, 17, 353-65.
176. Rademaker-Lakhai, J.M.; van den Bongard, D.; Pluim, D.; Beijnen, J.H.; Schellens, J.H. A Phase I and pharmacological study with imidazolium-trans-DMSO- imidazole-tetrachlororuthenate, a novel ruthenium anticancer agent. Clin. Cancer Res., 2004, 10, 3717-27.
177. Sava, G.; Zorzet, S.; Turrin, C.; Vita, F.; Soranzo, M.; Zabucchi, G.; Cocchietto, M.; Bergamo, A.; DiGiovine, S.; Pezzoni, G.; Sartor, L.; Garbisa, S. Dual action of NAMI-A in inhibition of solid tumor metastasis: selective targeting of metastatic cells and binding to collagen. Clin. Cancer Res., 2003, 9, 1898-905.
178. Sava, G.; Capozzi, I.; Clerici, K.; Gagliardi, G.; Alessio, E.; Mestroni, G. Pharmacological control of lung metastases of solid tumours by a novel ruthenium complex. Clin. Exp. Metastasis, 1998, 16, 371-9.
179. Sava, G.; Bergamo, A.; Zorzet, S.; Gava, B.; Casarsa, C.; Cocchietto, M.; Furlani, A.; Scarcia, V.; Serli, B.; Iengo, E.; Alessio, E.; Mestroni, G. Influence of chemical stability on the activity of the antimetastasis ruthenium compound NAMI-A. Eur. J. Cancer, 2002, 38, 427-35.
180. Bergamo, A.; Gagliardi, R.; Scarcia, V.; Furlani, A.; Alessio, E.; Mestroni, G.; Sava, G. In vitro cell cycle arrest, in vivo action on solid metastasizing tumors, and host toxicity of the antimetastatic drug NAMI-A and cisplatin. J. Pharmacol. Exp. Ther., 1999, 289, 559-64.
181. Sava, G.; Frausin, F.; Cocchietto, M.; Vita, F.; Podda, E.; Spessotto, P.; Furlani, A.; Scarcia, V.; Zabucchi, G. Actin-dependent tumour cell adhesion after short-term exposure to the antimetastasis ruthenium complex NAMI-A. Eur. J. Cancer, 2004, 40, 1383-96.
182. Frausin, F.; Scarcia, V.; Cocchietto, M.; Furlani, A.; Serli, B.; Alessio, E.; Sava, G. Free exchange across cells, and echistatin-sensitive membrane target for the metastasis inhibitor NAMI-A (imidazolium trans-imidazole dimethyl sulfoxide tetrachlororuthenate) on KB tumor cells. J. Pharmacol. Exp. Ther., 2005, 313, 227-33.
183. Pacor, S.; Zorzet, S.; Cocchietto, M.; Bacac, M.; Vadori, M.; Turrin, C.; Gava, B.; Castellarin, A.; Sava, G. Intratumoral NAMI-A treatment triggers metastasis reduction, which correlates to CD44 regulation and tumor infiltrating lymphocyte recruitment. Pharmacol. Exp. Ther., 2004, 310, 737-44.
184. Vacca, A.; Bruno, M.; Boccarelli, A.; Coluccia, M.; Ribatti, D.; Bergamo, A.; Garbisa, S.; Sartor, L.; Sava, G. Inhibition of endothelial cell functions and of angiogenesis by the metastasis inhibitor NAMI-A. Br. J. Cancer, 2002, 86, 993-8.
185. Zorzet, S.; Bergamo, A.; Cocchietto, M.; Sorc., A.; Gavia, B.; Alessio, E.; Iengo, E.; Sava, G. Lack of In vitro cytotoxicity, associated to increased G(2)-M cell fraction and inhibition of matrigel invasion, may predict In vivo-selective antimetastasis activity of ruthenium complexes. J. Pharmacol. Exp. Ther., 2000, 295, 927-33.
186. Nguyen, D.H.; Webb, D.J.; Catling, A.D.; Song, Q.; Dhakephalkar, A.; Weber, M.J.; Ravichandran, K.S.; Gonias, S.L. Urokinase-type plasminogen activator stimulates the Ras/Extracellular signal-regulated kinase (ERK) signaling pathway and MCF-7 cell migration by a mechanism that requires focal adhesion kinase, Src, and Shc. Rapid dissociation of GRB2/Sps-Shc complex is associated with the transient phosphorylation of ERK in urokinase-treated cells. J. Biol. Chem., 2000, 275, 19382-8.
187. Kobayashi, H.; Suzuki, M.; Tanaka, Y.; Hirashima, Y.; Terao, T. Suppression of urokinase expression and invasiveness by urinary trypsin inhibitor is mediated through inhibition of protein kinase C-and MEK/ERK/c-Jun-dependent signaling pathways. J. Biol. Chem., 2001, 276, 2015-22.
188. Pintus, G.; Tadolini, B.; Posadino, A.M.; Sanna, B.; Debidda, M.; Bennardini, F.; Sava, G.; Ventura, C. Inhibition of the MEK/ERK signaling pathway by the novel antimetastatic agent NAMI-A down regulates c-myc gene expression and endothelial cell proliferation. Eur. J. Biochem., 2002, 269, 5861-70.
189. Fadeel, B.; Ottosson, A.; Pervaiz, S. Big wheel keeps on turning: apoptosome regulation and its role in chemoresistance. Cell Death Differ., 2008, 15, 443-52.
190. Bruey, J.M.; Ducasse, C.; Bonniaud, P.; Ravagnan, L.; Susin, S.A.; Diaz-Latoud, C.; Gurbuxani, S.; Arrigo, A.P.; Kroemer, G.; Solary, E.; Garrido, C. Hsp27 negatively regulates cell death by interacting with cytochrome c. Nat. Cell Biol., 2000, 2, 645-52.
191. Sanna, B.; Debidda, M.; Pintus, G.; Tadolini, B.; Posadino, A.M.; Bennardini, F.; Sava, G.; Ventura, C. The anti-metastatic agent imidazolium trans-imidazoledimethylsulfoxide-tetrachlororuthenate induces endothelial cell apoptosis by inhibiting the mitogenactivated protein kinase/extracellular signal-regulated kinase signaling pathway. Arch. Biochem. Biophys., 2002, 403, 209-18.
192. Nikitenko, L.L. Vascular endothelium in cancer. Cell Tissue Res., 2009, 335, 223-40.
193. 3 requirement for sustained mitogen-activated protein kinase activity during angiogenesis. J. Cell Biol., 1998, 140, 1255-63.
194. Hüser, M.; Luckett, J.; Chiloeches, A.; Mercer, K.; Iwobi, M.; Giblett, S.; Sun, X.M.; Brown, J.; Marais, R.; Pritchard, C. MEK kinase activity is not necessary for Raf-1 function. EMBO J., 2001, 20, 1940-51.
195. Rabik, C.A.; Dolan, M.E. Molecular mechanisms of resistance and toxicity associated with platinating agents. Cancer Treat. Rev., 2007, 33, 9-23.
196. Barve, V.; Ahmed, F.; Adsule, S.; Banerjee, S.; Kulkarni, S.; Katiyar, P.; Anson, C.E.; Powell, A.K.; Padhye, S.; Sarkar, F.H. Synthesis, molecular characterization, and biological activity of novel synthetic derivatives of chromen-4-one in human cancer cells. J. Med. Chem., 2006, 49, 3800-8.
197. Adsule, S.; Barve, V.; Chen, D.; Ahmed, F.; Dou, Q.P.; Padhye, S.; Sarkar, F.H. Novel Schiff base copper complexes of quinoline-2 carboxaldehyde as proteasome inhibitors in human prostate cancer cells. J. Med. Chem., 2006, 49, 7242-6.
198. Hochstrasser, M.; Deng, M.; Kusmierczyk, A.R.; Li, X.; Kreft, S.G.; Ravid, T.; Funakoshi, M.; Kunjappu, M.; Xie, Y. Molecular genetics of the ubiquitin-proteasome system: lessons from yeast. Ernst Schering Found. Symp. Proc., 2008, 1, 41-66.
199. Thorpe, J.A.; Christian, P.A.; Schwarze, S.R. Proteasome inhibition blocks caspase-8 degradation and sensitizes prostate cancer cells to death receptor-mediated apoptosis. Prostate, 2008, 68, 200-9.
200. Milacic, V.; Chen, D.; Giovagnini, L.; Diez, A.; Fregona, D.; Dou, Q.P. Pyrrolidine dithiocarbamate-zinc(II) and -copper(II) complexes induce apoptosis in tumor cells by inhibiting the proteasomal activity. Toxicol. Appl. Pharmacol., 2008, 231, 24-33.
201. Cvek, B.; Milacic, V.; Taraba, J.; Dou, Q.P. Ni(II), Cu(II), and Zn(II) diethyldithiocarbamate complexes show various activities against the proteasome in breast cancer cells. J. Med. Chem., 2008, 51, 6256-8.
202. Xio, Y.; Bi, C.; Fan, Y.; Cui, C.; Zhang, X.; Dou, Q.P. L-glutamine Schiff base copper complex as a proteasome inhibitor and an apoptosis inducer in human cancer cells. Int J. Oncol., 2008, 33, 1073-9.
203. Daniel, K.G.; Chen, D.; Orlu, S.; Cui, Q.C.; Miller, F.R.; Dou, Q.P. Clioquinol and pyrrolidine dithiocarbamate complex with copper to form proteasome inhibitors and apoptosis inducers in human breast cancer cells. Breast Cancer Res., 2005, 7, R897-908.
204. Cerchiaro, G.; Aquilano, K.; Filomeni, G.; Rotilio, G.; Ciriolo, M.R.; Ferreira, A.M. Isatin-Schiff base copper(II) complexes and their influence on cellular viability. J. Inorg. Biochem., 2005, 99, 1433-40.
205. Thati, B.; Noble, A.; Creaven, B.S.; Walsh, M.; Kavanagh, K.; Egan, D.A. Apoptotic cell death: a possible key event in mediating the in vitro anti-proliferative effect of a novel copper(II) complex, [Cu(4-Mecdoa)(phen)(2)] (phen=phenanthroline, 4-Mecdoa=4-methylcoumarin-6,7-dioxactetate), in human malignant cancer cells. Eur. J. Pharmacol., 2007., 569, 16-28.
206. Hammud, H.H.; Nemer, G.; Sawma, W.; Touma, J.; Barnabe, P.; Bou-Mouglabey, Y.; Ghannoum, A.; El-Hajjar, J.; Usta, J. Copperadenine complex, a compound, with multi-biochemical targets and potential anti-cancer effect. Chem. Biol. Interact., 2008, 173, 84-96.
207. Hasenknopf, B. Polyoxometalates: introduction to a class of inorganic compounds and their biomedical applications. Front. Biosci., 2005, 10, 275-87.
208. Yanagie, H.; Ogata, A.; Mitsui, S.; Hisa, T.; Yamase, T.; Eriguchi, M. Anticancer activity of polyoxomolybdate. Biomed. Pharmacother., 2006, 60, 349-52.
209. Lowndes, S.A.; Harris, A.L. The role of copper in tumour angiogenesis. J. Mamm Gland Biol. Neoplasia, 2005, 10, 299-310.
210. Brewer, G.J.; Dick, R.D.; Grover, D.K.; Leclaire, V.; Tseng, M.; Wicha, M.; Pienta, K.; Redman, B.G.; Jahan, T.; Sondak, V.K.; Strawderman, M.; LeCarpentier, G.; Merajver, S.D. Treatment of metastatic cancer with tetrathiomolybdate, an anticopper, antiangiogenic agent: Phase I study. Clin. Cancer Res., 2000, 6, 1-10.
211. Pass, H.I.; Brewer, G.J.; Dick, R.; Carbone, M.; Merajver, S. A phase II trial of tetrathiomolybdate after surgery for malignant mesothelioma: final results. Ann. Thorac. Surg., 2008, 86, 383-9.
212. Redman, B.G.; Esper, P.; Pan, Q.; Dunn, R. I.; Hussain, H.K.; Chenevert, T.; Brewer, G.J.; Merajver, S.D. Phase II trial of tetrathiomolybdate in patients with advanced kidney cancer. Clin. Cancer Res., 2003, 9, 1666-72.