Activation of the trans Geometry in Platinum Antitumor Complexes: A Survey of the Cytotoxicity of trans Complexes Containing Planar Ligands in Murine LI 210 and Human Tumor Panels and Studies on Their Mechanism of Action

Cancer Research

Volumn 52, Issue 18, 1992, Pages 5065-5072

  Kelland, Lloyd R ^c,d   Beusichem, Marijo Van ^a  

^a Department of Chemistry ^*  (United States)

^b Departments of Social Medicine Medicine and Epidemiology   (United States)

^c UNIVERSITY OF VERMONT   (United States)

^d INSTITUTE OF CANCER RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CISPLATIN; TRANSPLATIN;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; CANCER SCREENING; CARCINOMA CELL; CELL INTERACTION; CROSS RESISTANCE; CYTOTOXICITY; DNA BINDING; DNA SYNTHESIS INHIBITION; GENETIC COMPLEMENTATION; HUMAN; HUMAN CELL; LEUKEMIA CELL; LIGAND BINDING; NONHUMAN; OVARY CARCINOMA; PRIORITY JOURNAL; TUMOR CELL LINE;

ANIMAL; ANTINEOPLASTIC AGENTS; BIOLOGICAL TRANSPORT; DNA; FEMALE; GLUTATHIONE; HUMAN; IN VITRO; ISOMERISM; LEUKEMIA L1210; MICE; ORGANOPLATINUM COMPOUNDS; OVARIAN NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.; TUMOR CELLS, CULTURED;

EID: 0026803014     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. Reed, E., and Kohn, K. W. Platinum analogs. In: B. A. Chabner and J. Collins, (eds.). Cancer Chemotherapy: Principles and Practice, pp. 465-490. Philadelphia: J. B. Lippincott, 1990.
2. Farrell, N. Platinum-amine complexes as anticancer agents. In: B. R. James and R. Ugo (eds.). Catalysis by Metal Complexes, pp. 46-66. Dordrecht: Reidel-Kluwer Academic Publishers, 1989.
3. Giandomenico, C. M., Abrams, M. J., Murrer, B. A., Vollano, J. F., Harrap, K. R., Goddard, P. M., Kelland, L. R., and Morgan, S. E. Synthesis and reactions of a new class of orally active Pt(IV) antitumor complexes. In: S. B. Howell (ed.). Proceedings of the Sixth International Symposium on Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy, pp. 93-100. New York: Plenum Press, 1991.
4. Canetta, R., Rozencweig, M., Wittes, R. E., and Schacter, L. P. Platinum coordination complexes in cancer chemotherapy: an historical perspective. In: K. Kimura, K. Yamada, S. K. Carter, D. P. Griswold, Jr. (eds.). Cancer Chemotherapy: Challenges for the Future, Vol. 5, pp. 318-323. Tokyo: Excerpta Medica, 1990.
5. Eisenhauer, E., Swerton, K., Sturgeon, J., Fine, S., O'Reilly, S., and Canetta, R. Carboplatin therapy for recurrent ovarian carcinoma: National Cancer Institute of Canada experience and a review of the literature. In: P. Bunn, R. Canetta, R. Ozols, and M. Rozencweig (eds.), Carboplatin: Current Perspectives and Future Directions, pp. 133-140. Philadelphia: W. B. Saunders, 1990.
6. Van Beusichem, M., and Farrell, N. Activation of the trans geometry in platinum antitumor complexes. Synthesis, characterisation and biological activity of complexes with planar ligands pyridine, N-methylimidazole, thiazole and quinoline. The crystal and molecular structure of trams-dichlorobis-(thiazole)platinum(ll). Inorg. Chem., 31:634-639, 1992.
7. Hills, C. A., Kelland, L. R., Abel, G., Siracky, J., Wilson, A. P., and Harrap, K. R. Biological properties of ten human ovarian carcinoma cell lines: calibration in vitro against four platinum complexes. Br. J. Cancer, 59:527-534, 1989.
8. Kelland, L. R., Mistry, P., Abel, G., Loh, S. Y., O'Neill, C. F., Murrer, B. A., and Harrap, K. R. Mechanism-related circumvention of cis-diamminedichloroplatinum(II) acquired resistance in two pairs of human ovarian carcinoma cell lines by ammine/amine platinum(IV) dicarboxylates. Cancer Res., 52: 3857-3864, 1992.
9. Kelland, L. R., Murrer, B. A., Abel, G., Giandomenico, C. M., Mistry, P., and Harrap, K. Ammine/amine platinum(IV) dicarboxylates: a novel class of platinum complex exhibiting selective cytotoxicity to intrinsically cisplatin-resistant human ovarian carcinoma cell lines. Cancer Res., 52: 822-828, 1992.
10. Boyd, M. R. Status of the NCI preclinical antitumor drug discovery screen. Princ. Pract. Oncol. Updates, 3: 1-12, 1989.
11. Snedecor, G. W., and Cochran, W. G. Statistical Methods, Ed. 6, pp. 194-195. Ames, lA: Iowa State University Press, 1967.
12. Pauli, K. D., Shoemaker, R. H., Modes, L., Monks, A., Scudeiro, D. A., Rubinstein, L., Plowman, J., and Boyd, M. R. Display and analysis of patterns of differential activity of drugs against human tumor cell lines: development of mean graph and COMPARE algorithm. J. Natl. Cancer Inst., 81: 1088-1092, 1989.
13. Farrell, N., Kiley, D. M., Schmidt, W., and Hacker, M. P. Chemical properties and antitumor activity of complexes of platinum containing substituted sulfoxides [PtCl(/f/PS0)(diamine))N03. Chirality and leaving-group ability of sulfoxide affecting biological activity. Inorg. Chem., 29: 397-403, 1990.
14. Sundquist, W. I., Ahmed, K. J., Hollis, L. S., and Lippard, S. J. Solvolysis reactions of cis- and trans-diamminedichloroplatinum(II) in dimethyl sulfoxide. Structural characterization and DNA binding of trans-(Pt(NH3)2-(Me2SO)Cl]-. Inorg. Chem., 26: 1524-1530, 1987.
15. Wehrli, W., and Staehelin, M. Actions of rifamycins. Bacteriol. Rev., 35: 290-309, 1971.
16. Waud, W. R. Differential uptake of cis-diamminedichloroplatinum(II) by sensitive and resistant murine LI210 leukemia cells. Cancer Res., 47:6549-6555, 1987.
17. Kraker, A. J., and Moore, C. W. Accumulation of cis-diamminedichloroplatinum(II) and platinum analogues by platinum-resistant murine leukemia cells in vitro. Cancer Res., 48: 9-13, 1988.
18. Andrews, P. A., Velury, S., Mann, S. C., and Howell, S. B. cis-Diamminedichloroplatinum(II) accumulation in sensitive and resistant human ovarian carcinoma cells. Cancer Res., 48:68-73, 1988.
19. Bungo, M., Fujiwara, Y., Kasahara, K., Nakagawa, K., Ohe, Y., Sasaki, Y., Irino, S., and Saijo, N. Decreased accumulation as a mechanism of resistance to cis-diamminedichlorplatinum(II) in human non-small cell lung cancer cell lines: relation to DNA damage and repair. Cancer Res., 50: 2549-2553, 1990.
20. Harder, H. C., and Rosenberg, B. Inhibitory effects of anti-tumor platinum compounds on DNA, RNA and protein syntheses in mammalian cells in vitro. Int. J. Cancer, 6: 207-216, 1970.
21. Johnson, N. P., Butour, J-L., Villani, G., Wimmer, F. L., Defais, M., Pierson, V., and Brabec, V. Metal antitumor compounds: the mechanism of action of platinum complexes. Prog. Clin. Biochem. Med., 10: 1-24, 1989.
22. Hospers, G. A. P., Mulder, N. H., de Jong, B., de Ley, L., Uges, D. R. A., Fichtinger-Schepman, A. M. J., Scheper, R. J., and de Vries, E. G. E. Characterization of a human small cell lung carcinoma cell line with acquired resistance to cis-diamminedichloroplatinum(II) in vitro. Cancer Res., 48: 6803-6807, 1988.
23. Mistry, P., Kelland, L. R., Abel, G., Sidhar, S., and 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, 64: 215-220, 1991.
24. Teicher, B. A., Holden, S. A., Herman, T. S., Alvarez Sotomayer, E., Khandekar, V., Rosbe, K. W., Brann, T. W., Korbut, T. T., and Frey, E., III. Characteristics of five human tumor cell lines and sublines resistant to cis-diamminedichloroplatinum(II). Int. J. Cancer, 47: 252-260, 1991.
25. Kelley, S. L., Basu, A., Teicher, B. A., Hacker, M. P., Hamer, D. H., and Lazo, J. S. Overexpression of metallothionein confers resistance to anticancer drugs. Science (Washington DC), 241: 1813-1815, 1988.
26. Eastman, A., and Barry, M. A. Interaction of trans-diamminedichloroplatinum(II) with DNA: formation of monofunctional adducts and their reaction with glutathione. Biochemistry, 26: 3303-3307, 1987.
27. 195Pt NMR kinetic and mechanistic studies of cis- and trans-diamminedichloroplatinum(II) binding to DNA. J. Am. Chem. Soc., 112:6860-6871, 1990.
28. 1H DEPT NMR. J. Inorg. Biochem., 38: 327-351, 1990.
29. Berners-Price, S. J., and Kuchel, P. W. Reaction of cis- and /ras-[PtCl2-(NH3)2] with reduced glutathione studied by 1H, 13C, and 15N-1H DEPT NMR. J. Inorg. Biochem., 38: 305-326, 1990.
30. Djuran, M. I., Lempers, E. L. M., and Reedijk, J. Reactivity of chloro- and aqua(diethylenetriamine)platinum(II) ions with glutathione, S-methylglutathione, and guanosine 5'-monophosphate in relation to the antitumor activity and toxicity of platinum complexes. Inorg. Chem., 30: 2648-2652, 1991.
31. Scanlon, K. J., Kashani-Sabet, M., Miyachi, H., Sowers, L. C., and Rossi, J. Molecular basis of cisplatin resistance in human carcinomas: model systems and patients. Anticancer Res., 9: 1301-1312, 1989.
32. Richon, V. M., Schulte, N., and Eastman, A. Multiple mechanisms of resistance to cis-Diamminedichloroplatinum(U) in murine leukemia LI210 cells. Cancer Res., 47: 2056-2061, 1987.
33. Andrews, P. A., and Howell, S. B. Cellular pharmacology of cisplatin: perspectives on mechanisms of acquired resistance. Cancer Cells, 2: 35-43, 1990.
34. Christian, M. C., Spriggs, D., Tutsch, K. D., O'Rourke, T., VonHoff, D. D., Jacob, J. L., and Reed, E. Phase 1 trials with Ormaplatin (tetraplatin). In: S. B. Howell (ed.). Proceedings of the Sixth International Symposium on Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy, pp. 453-458. New York: Plenum Press, 1990.