Alkyl esters of camptothecin and 9-nitrocamptothecin: Synthesis, in vitro pharmacokinetics, toxicity, and antitumor activity

Journal of Medicinal Chemistry

Volumn 41, Issue 1, 1998, Pages 31-37

  Cao, Zhisong ^a   Harris, Nick ^a   Kozielski, Anthony ^a   Vardeman, Dana ^a   Stehlin, John S ^a   Giovanella, Beppino ^a  

^a St Joseph's Medical Center Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

9 AMINOCAMPTOTHECIN; ACID ANHYDRIDE; CAMPTOTHECIN; CAMPTOTHECIN DERIVATIVE; CYCLOHEXANECARBOXYLIC ACID DERIVATIVE; CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; IRINOTECAN; LACTONE; PRODRUG; RUBITECAN; TOPOTECAN;

ACYLATION; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; BREAST CARCINOMA; COLON CARCINOMA; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INTRAGASTRIC DRUG ADMINISTRATION; LUNG CARCINOMA; NONHUMAN; NUDE MOUSE; STRUCTURE ACTIVITY RELATION; TUMOR XENOGRAFT;

ACYLATION; ALKYLATION; ANIMALS; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CAMPTOTHECIN; FEMALE; HUMANS; MICE; MICE, NUDE; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSPLANTATION, HETEROLOGOUS;

EID: 0031952835     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9607562     Document Type: Article

References (36)

1. Wall, M. E.; Wani, M. C.; Cook, C. E.; Palmer, K H.; McPhail, A. T.; Sim, G. A. Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from camptotheca acuminata. J. Am. Chem. Soc. 1966, 88, 3888-3890.
2. Gottlieb, J. A.; Guarino, A. M.; Call, J. B.; Oliverio, V. T.; Block, J. B. Preliminary pharmacologie and clinical evaluation of camptothecin sodium (NSC-100880). Cancer Chemother. Rep., Part 1 1970, 54, 461-470.
3. Gottlieb, J. A.; Luce, J. K. Treatment of malignant melanoma with camptothecin (NSC-100880). Cancer Chemother. Rep. 1972, 56, 103-105.
4. Muggia, F. M.; Creaven, P. J.; Hansen, H. H.; Cohen, M. H.; Selawry, O. S. Phase I clinical trial of weekly and ..daily treatment with camptothecin (NSC-100880): Correlation with preclinical studies. Cancer Chemother. Rep. 1972, 56, 515-521.
5. Moertel, C. G.; Schutt, A. J.; Reitemeier, R. J.; Hahn, R. G. Phase II study of camptothecin (NSC-100880) in the treatment of advanced gastrointestinal cancer. Cancer Chemother. Rep. 1972, 56, 95-101.
6. Schaeppi, U.; Fleishman, R. W.; Cooney, D. A. Toxicity of camptothecin (NSC-100880). Cancer Chemother. Rep., Part 3 1974, 5, 25-36.
7. Hsiang, Y.-H.; Hertzberg, R.; Hecht, S.; Liu, L. F. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I. J. Biol, Chem. 1985, 260, 14873-14878.
8. Hsiang, Y.-H.; Liu, L. F. Identification of mammalian DNA topoisomerase I as an intracellular target of the anticancer drug camptothecin. Cancer Res. 1988, 49, 1722-1726.
9. Jaxel, C.; Kohn, K W.; Wani, M. C.; Wall, M. E.; Pommier, Y. Structure-activity study of the actions of camptothecin derivatives on mammalian topoisomerase. I. Evidence for a specific receptor site and a relation to antitumor activity. Cancer Res. 1989, 49, 1465-1469.
10. Hsiang, Y.-H.; Liu, L. F.; Wall, M. E.; Wani, M. C.; Nicholas, A. W.; Manikumar, G.; Kischenbaum, S.; Silber, R.; Potmesil, M. DNA Topoisomerase I-mediated DNA cleavage and cytotoxicity of camptothecin analogues. Cancer Res. 1989, 49, 4385-4389.
11. Osheroff, N. Biochemical basis for the interactions of type I and type II topoisomerases with DNA. Pharmacol. Ther. 1989, 41, 223-241.
12. Plattner, J. J.; Gless, R. D.; Cooper, G. K.; Rapport, H. Synthesis of some DE and CDE ring analogues of camptothecin. J. Org. Chem. 1974, 39, 303-311.
13. Danishefsky, S.; Etheredge, S. J. Synthesis and biological evaluation of DE-AB-camptothecin. J. Org. Chem. 1974, 39, 3430-3432.
14. Bristol, J. A.; Comins, D. L.; Davenport, R. W.; Kane, M. J.; Lyle, R. E.; Maloney, J. R.; Portlock, D. E. Analogues of camptothecin. J. Med. Chem. 1975, 18, 535-537.
15. Sugasaawa, T.; Toyoda, T.; Uchida, N.; Yamaguchi, K. Experiments on the synthesis of dl-camptothecin. 4. Synthesis and antileukemic activity of dl-camptothecin analogues. J. Med. Chem. 1976, 19, 675-679.
16. Wani, M. C.; Ronman, P. E.; Lindley, L. T.; Wall, M. E. Plant antitumor agents. 18. Synthesis and biological activity of camptothecin analogues J. Med. Chem. 1980, 23, 554-560.
17. Wani, M. C.; Nicholas, A. W.; Wall, M. E. Plant antitumor agents. 23. Synthesis and antileukemic activity of camptothecin analogues. J. Med. Chem. 1986, 29, 2358-2363.
18. Wani, M. C.; Nicholas, A. W.; Manikumar, G.; Wall, M. E. Plant antitumor agents. 25. Total synthesis and antileukemic activity of ring A substituted camptothecin analogues. Structureactivity correlations. J. Med. Chem. 1987, 30, 1774-1779.
19. Nicholas, A. W.; Wani, M. C.; Manikumar, G.; Wall, M. E.; Kohn, K. W.; Pommier, Y. Plant Antitumor Agent. 29. Synthesis and biological activity of ring D and ring E modified analogues of camptothecin. J. Med. Chem. 1990, 33, 972-978.
20. Kingsburg, W. D.; Boehm, J. C.; Jakas, D. R.; Holden, K. G.; Hecht, S. M.; Glagher, G.; Caranfa, M. J.; McCabe, F. L.; Faucette, L. F.; Johnson, R. K.; Hertzberg, R. P. Synthesis of water soluble (aminoalkyl)camptothecin analogues: Inhibition of topoisomerase I and antitumor activity. J. Med. Chem. 1991, 34, 98-107.
21. Ejima, A.; Terasawa, H.; Sugimori, M.; Ohsuki, S.; Matsumoto, K.; Kawato, Y.; Yasuoka, M.; Tagawa, H. Antitumor agents. V. Synthesis and antileukemic activity of E-ring modified (RS)camptothecin. Chem. Pharm. Bull. 1992, 40, 683-688.
22. Yaegashi, T.; Sawada, S.; Nagata, H.; Furata, T.; Yokokura, T.; Miyasaka, T. Synthesis and antitumor activity of 20(S)-camptothecin derivatives. A-ring-substituted 7-ethylcamptothecins and their E-ring-modified water soluble derivatives. Chem. Pharm. Bull. 1994, 42 (12), 2518-2525.
23. Peel, M. R.; Steinback, D. D. The synthesis and evaluation of flexible analogues of the topoisomerase I inhibitor, camptothecin. Bioorg. Med. Chem. Lett. 1994, 4 (23), 2753-2758.
24. Wang, H.-K.; Liu, S.-Y.; Hwang, K.-W.; McPhail, A. T.; Lee, KH. Antitumor agents. 160. The synthesis of 5-substituted camptothecins as potential inhibitor of DNA topoisomerase I. Bioorg. Med. Chem. Lett. 1995, 5 (1), 77-82.
25. Luzzio, M. J.; Besterman, J. M.; Emerson, D. L.; Evans, M. G.; Lackey, K.; Leitner, P. L. Synthesis and antitumor activity of novel water soluble derivatives of camptothecin as specific inhibitors of topoisomerase I. J. Med. Chem. 1995, 38 (3), 395-401.
26. Syder, L.; Shen, W.; Bornmann, W. G.; Danishefsky, S. I. Synthesis of 18-noranhydrocamptothecin analogues which retain topoisomerase I inhibitory function. J. Org. Chem. 1994, 59 (23), 7033-7037.
27. Fang, F.; Xie, S.; Lowery, M. W. Catalytic enantioselective synthesis of 20(S)-camptothecin: A practical application of the sharpless asymmetric dihydroxylation reaction. J. Org. Chem. 1994, 59 (21), 6142-6143.
28. Comins, D. L.; Hao, H.; Gao, J. Asymmetric synthesis of camptothecin alkaloids: A nine step synthesis of (S)-camptothecin. Tetrahedron Lett. 1994, 35 (30), 5331-5334.
29. Rama Rao, A. V.; Yadav, J. S.; Valluri, M. Regioselective synthesis of camptothecin. Tetrahedron Lett. 1994, 35 (21), 3613-3616.
30. Giovanella, B. C.; Stehlin, J. S.; Wall, M. E.; Wani, M. C.; Nicholas, A. W.; Liu, L. F.; Silber, R.; Potmesil, M. DNA topoisomerase I-targeted chemotherapy of human colon cancer in xenografts. Science 1989, 246, 1046-1048.
31. Sawada, S.; Matsuoka, S.; Nokata, K.; Nagata, H.; Furuta, T.; Yokokura, T.; Miyasaka, T. Synthesis and antitumor activity of 20(S)-camptothecin derivatives: A-ring modified and 7, 10disubstituted camptothecins. Chem. Pharm. Bull. 1991, 39, 3183-3188.
32. Giovanella, B. C.; Hinz, H. R.; Kozielski, A. J.; Stehlin, J. S., Jr.; Silber, R.; Potmesil, M. Complete growth inhibition of human cancer xenografts in nude mice by treatment with 20(S) camptothecin. Cancer Res. 1991, 57, 3052-3055.
33. Giovanella, B. C.; et al. Unpublished results.
34. Giovanella, B. C.; et al. Unpublished results.
35. Wall, M. E.; Wani, M. C.; Nicholas, A. W.; Manikumar, G.; Tele, C.; Moore, L.; Truesdale, A.; Leitner, P.; Besterman, J. M. Plant antitumor agents. 30. Synthesis and structure-activity of novel camptothecin analogues. J. Med. Chem. 1993, 36, 2689-2700.
36. Giovanella, B. C.; Stehlin, J. S. Heterotransplantation of human malignant tumors in "nude" thymusless mice. I. Breeding and maintenance of "nude" mice. J. Natl. Cancer Inst. 1973, 51, 615-617.