Cytotoxicity and Antitumor Activity of Carzelesin, a Prodrug Cyclopropylpyrroloindole Analogue

Cancer Research

Volumn 52, Issue 18, 1992, Pages 4904-4913

  Li, L H ^a   DeKoning, T F ^a   Kelly, R C ^a   Krueger, W C ^a   McGovren, J P ^a   Padbury, G E ^a   Petzold, G L ^a   Wallace, T L ^a   Ouding, R J ^a   Prairie, M D ^a   Gebhard, I ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADOZELESIN; CARZELESIN; CYCLOPROPANE DERIVATIVE; DNA; DRUG ANALOG; INDOLE DERIVATIVE; PRODRUG; PYRROLE DERIVATIVE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CANCER REGRESSION; COLON CARCINOMA; CONTROLLED STUDY; DOG; DRUG ABSORPTION; DRUG CLEARANCE; DRUG CYTOTOXICITY; DRUG DISTRIBUTION; DRUG DNA INTERACTION; DRUG EFFICACY; DRUG POTENCY; HUMAN; HUMAN CELL; INTRAPERITONEAL DRUG ADMINISTRATION; INTRAVENOUS DRUG ADMINISTRATION; LEUKEMIA; LUNG CARCINOMA; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; OVARY CARCINOMA; PANCREAS CARCINOMA; PRIORITY JOURNAL; RAT; SUBCUTANEOUS DRUG ADMINISTRATION; TUMOR XENOGRAFT;

ADENOCARCINOMA; ANIMAL; ANTINEOPLASTIC AGENTS; CELL SURVIVAL; COLONIC NEOPLASMS; CULTURE MEDIA; INDOLES; LEUKEMIA L1210; METABOLIC CLEARANCE RATE; MICE; MICE, NUDE; NEOPLASM TRANSPLANTATION; PANCREATIC NEOPLASMS; PLASMA; PRODRUGS; TRANSPLANTATION, HETEROLOGOUS;

EID: 0026786973     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. Reynolds, V. L., McGovren, J. P., and Hurley, L. H. The chemistry, mechanism of action and Biological properties of CC-106S, a potent antitumor antibiotic. J. Antibiot. (Tokyo), S9:319-334, 1986.
2. Wierenga, W., Bhuyan, B. K., Kelly, R. C., Krueger, W. C., Li, L. H., McGovren, J. P., Swenson, D. H., and Warpehoski, M. A. Antitumor activity and biochemistry of novel analogs of the antibiotic, CC-106S. Adv. Enzyme Regul., 25: 141-155, 1986.
3. Li, L. H., Wallace, T. L., DeKoning, T. F., Warpehoski, M. A., Kelly, R. C., Prairie, M. D., and Krueger, W. C. Structure and activity relationship of several novel CC-1065 analogs. Invest. New Drugs, 5: 329-337, 1987.
4. Warpehoski, M. A., and Hurley, L. H. Sequence selectivity of DNA covalent modification. Chem. Res. Toxicol., I: 315-333, 1988.
5. Warpehoski, M. A. Dissecting the complex structure of CC-1065. Drugs Future, 16:131-141, 1991.
6. Aristoff, P. A. CC-1065 analogs: sequence-specific DNA-alkylating antitumor agents. Adv. Med. Chem., in press.
7. Li, L. H., Kelly, R. C., Warpehoski, M. A., McGovren, J. P., Gebhard, I., and DeKoning, T. F. Adozelesin, a selected lead among cyclopropylpyrroloindole analogs of the DNA-binding antibiotic, CC-1065. Invest. New Drugs, 9: 137-148, 1991.
8. Swenson, D. H., Li, L. H., Hurley, L. H., Rokem, J. S., Petzold, G. L., Dayton, B. D., Wallace, T. L., Lin, A. H., and Krueger, W. C. Mechanism of interaction of CC-1065 (NSC 298223) with DNA. Cancer Res., 42: 2821-2828, 1982.
9. Li, L. H., Swenson, D. H., Schpok, S. L., Kuentzel, S. L., Dayton, B. D., and Krueger, W. C. CC-1065 (NSC 298223), a novel antitumor agent that interacts strongly with double-stranded DNA. Cancer Res., 42:999-1004,1982.
10. Warpehoski, M. A., and Bradford, V. S. Regioselective (2,3) sigmatropic rearrangement to the pyrrolo(3,2-e)indole ring system of CC-1065. Tetrahedron Utt., 27: 2735-2738, 1986.
11. Kelly, R. C., Gebhard, L., Wicnienski, N., AristofT, P. A., Johnson, P. D., and Martin, D. G. Coupling of cyclopropapyrroloindole (CPI) derivatives. The preparation of CC-1065, ent-CC-1065, and analogs. J. Am. Chem. Soc., 109: 6837-6838, 1987.
12. Warpehoski, M. A., Gebhard, I., Kelly, R. C., Krueger, W. C., Li, L. H., McGovren, J. P., Pnurie, M. D., Wicnienski, N., and Wierenga, W. Stereo-electronic factors influencing the Biological activity and DNA interaction of synthetic antitumor agents modeled on CC-1065. J. Med. Chem., 31: 590-603, 1988.
13. Hurley, L. H., Warpehoski, M. A., Lee, C-S., McGovren, J. P., ScahUl, T. A., Kelly, R. C., Mitchell, M. A., Wicnienski, N. A., Gebhard, I., Johnson, P. D., and Bradford, V. S. Sequence specificity of DNA alkylation by the unnatural enantiomer of CC-1065 and its synthetic analogs. J. Am. Chem. Soc., 112: 4633-4649, 1990.
14. Li, L. H., Kuentzel, S. L., Murch, L. L., Pschigoda, L. M., and Krueger, W. C. Comparative Biological and biochemical effects of nogalamycin and its analogs on L1210 leukemia. Cancer Res., 39:4816-4822, 1979.
15. Krueger, W. C., Pschigoda, L. M., Schpok, S. L. F., Moscowitz, A., McGovren, J. P., Neta, P., Merritt, M. V., and Li, L. H. The interaction of nogalamycin and analogs with DNA and other biopolymers. Chem. Biol. Interact., 36: 1-18, 1981.
16. United Sutes National Cancer Institute. In Vivo Cancer Models. NIH Publication 84-2635, 1984.
17. Goldin, A., Venditti, J. M., and Carter, S. K. Screening at the National Cancer Institute. Natl. Cancer Inst. Monogr., 45: 37-48, 1977.
18. Giovanella, B. C., Shepard, R. C., Stehlin, J. S., Venditti, J. M., and Abbott, B. J. Calorie restriction: effect on growth of human tumors heterotransplanted in nude mice. J. Natl. Cancer Inst. 68: 249-257, 1982.
19. Krueger, W. C., and Prairie, M. D. The origin of the DNA induced circular dichroism of CC-1065 and analogs. Chem. Biol. Interact., 79: 137-149, 1991.
20. Corbett, T. H., Roberts, B. J., Leopold, W. R., Peckham, J. C., Wilkoff, L. J., Griswold, D. P., Jr., and Schabel, F. M., Jr. Induction and chemotherapeutic response of two transplantable ductal adenocarcinomas of the pancreas in C57BL/6 mice. Cancer Res., 44:717-726, 1984.
21. Goldin, A., Venditti, J. M., MacDonald, J. S., Muggia, F. M., Henney, J. E., and Devita, V. T., Jr. Current results of the screening program at the Division of Cancer Treatment, National Cancer Institute. Eur. J. Cancer, 17:129-142, 1981.
22. Staquet, M. J., Byar, D. P., Green, S. B., and Rozenweig, M. Clinical predictivity of transplantable tumor systems in the selection of new drugs for solid tumors: rationale for a three-stage strategy. Cancer Treat. Rep., 67: 153-165, 1983.
23. DeKoning, T. F., Kelly, R. C., Wallace, T. L., and Li, L. H. Antitumor activity and biochemical effect of three selected cyclopropapyrroloindole (CPI) analogs. Proc. Am. Assoc. Cancer Res., 30:491, 1989.
24. DeKoning, T. F., Postmus, R. J., Wallace, T. L., Kelly, R. C., and Li, L. H. Therapeutic evaluation of three cyclopropapyrroloindole analogs against human tumor xenografts. Proc. Am. Assoc. Cancer Res., 31: 348, 1990.
25. Wierenga, W. Sequence-selective DNA-interactive antitumor agents. Drugs Future, 16: 741-750, 1991.
26. Li, L. H. U-80244, a novel lead among cyclopropylpyrroloindole analogs. In: Proceedings of the ARTAC Workshop on Therapeutic Trials in Cancer and AIDS, 1991.