7-Silylcamptothecins (silatecans): A new family of camptothecin antitumor agents

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 24, 1997, Pages 3189-3194

  Josien, Hubert ^a   David, Bom ^a   Curran, Dennis P ^a   Zheng, Yu Huang ^b   Chou, Ting Chao ^b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

10 AMINO 11 FLUORO 7 TRIMETHYLSILYLCAMPTOTHECIN; ANTINEOPLASTIC AGENT; CAMPTOTHECIN; CAMPTOTHECIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DNA CLEAVAGE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE;

EID: 0344074659     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10181-0     Document Type: Article

References (33)

1. (a) Camptothecins: New Anticancer Agents; Potmesil, H.; Pinedo, H., Eds.;CRC: Boca Raton, 1995.
2. (b) The Camptothecins. from Discovery to Patient; Pantaziz, P.; Giovannela, B. C., Eds.; Ann. NY Acad. Science, 1996, vol. 803.
3. (a) Hertzberg, R. P.; Caranfa, M. J.; Holden, K. G.; Jakas, D. R.; Gallagher, G.; Mattern, M. R.; Mong, S. M.; Bartus, J. O. L.; Johnson, R. K.; Kingsbury, W. D. J. Med. Chem. 1989, 32, 715.
4. (b) Snyder, L.; Shen, W.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 7033.
5. Ejima, A.; Terasawa, H.; Sugimori, M.; Ohsuki, S.; Matsumoto, K.; Kawato, Y.; Yasuoka, M.; Tagawa, H. Chem. Pharm. Bull. 1992, 40, 683.
6. Sawada, S.; Nokata, K.; Furuta, T.; Yokokura, T.; Miyasaki, T. Chem. Pharm. Bull. 1991, 39, 2574.
7. (a) Peel, M. R.; Sternbach, D. D. Bioorg. Med. Chem. Lett. 1994, 4, 2753.
8. b) Lackey, K.; Besterman, J. M.; Fletcher, W.; Leitner, P.; Morton, B.; Sternbach, D. D. J. Med. Chem. 1995, 38, 906.
9. Nicholas, A. W.; Wani, M. C.; Manikumar, G.; Wall, M. E.; Kohn, K. W.; Pommier, Y. J. Med. Chem. 1990, 33, 972.
10. Recent references: (a) Lackey, K.; Sternbach, D. D.; Croom, D. K.; Emerson, D. L.; Evans, M. G.; Leitner, P. L.; Luzzio, M. J.; McIntyre, G.; Vuong, A.; et al. J. Med. Chem. 1996, 39, 713.
11. (b) Luzzio, M. J.; Besterman, J. M.; Emerson, D. L.; Evans, M. G.; Lackey, K.; Leitner, P. L.; McIntyre, G.; Morton, B.; Myers, P. L.; Peel, M.; Sisco, J. M.; Sternbach, D. D.; Tong, W. Q.; Truesdale, A.; Uehling, D. E.; Vuong, A.; Yates, J. J. Med. Chem. 1995, 38, 395.
12. Wang, H. K.; Liu, S. Y.; Hwang, K. M.; Taylor, G.; Lee, K. H. Bioorg. Med. Chem. Lett. 1994, 4, 579.
13. Zhao, R.; Oreski, B.; Lown, J. W. Bioorg. Med. Chem. Lett. 1995, 5, 3063.
14. (e) Peel, M. R.; Milstead, M. W.; Sternbach, D. D.; Besterman, J. M.; Leitner, P.; Morton, B. Bioorg. Med. Chem. Lett. 1995, 5, 2129.
15. (f) Xie, Z.-F.; Ootsu, K.; Akimoto, H. Bioorg. Med. Chem. Lett. 1995, 5, 2189-94.
16. (g) Bedeschi, A.; Zarini, F.; Cabri, W.; Candiani, I.; Penco, S.; Capolongo, L.; Ciomei, M.; Farao, M.; Grandi, M. Bioorg. Med. Chem. Lett. 1996, 6, 671.
17. Modern version with enantiopure products: Wani, M. C.; Nicholas, A. W.; Wall, M.E.J. Med. Chem. 1987, 30, 2317-19.
18. Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1991, 113, 2127.
19. Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. Curran, D. P.; Liu, H.; Josien, H.; Ko, S. B. Tetrahedron 1996, 52, 11385.
20. Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. Curran, D. P.; Liu, H.; Josien, H.; Ko, S. B. Tetrahedron 1996, 52, 11385.
21. Curran, D. P.; Ko, S. B.; Josien, H. Angew. Chem. Int. Ed. 1995, 34, 2683. Josien, H., Ko, S.-B.,Curran, D. P. Chemistry, Eur. J., in press.
22. Curran, D. P.; Ko, S. B.; Josien, H. Angew. Chem. Int. Ed. 1995, 34, 2683. Josien, H., Ko, S.-B.,Curran, D. P. Chemistry, Eur. J., in press.
23. Liu, H.; Ko, S.-B.; Josien, H.; Curran, D. P. Tetrahedron Lett. 1995, 36, 8917.
24. Nanni, D.; Pareschi, P.; Rizzoli, C.; Sgarabotto, P.; Tundo, A. Tetrahedron 1995, 51, 9045. Nanni, D.; Pareschi, P.; Tundo, A. Tetrahedron Lett. 1996, 37, 9337.
25. Nanni, D.; Pareschi, P.; Rizzoli, C.; Sgarabotto, P.; Tundo, A. Tetrahedron 1995, 51, 9045. Nanni, D.; Pareschi, P.; Tundo, A. Tetrahedron Lett. 1996, 37, 9337.
26. Yaegashi, T.; Sawada, S.; Nagata, H.; Furuta, T.; Yokokura, T.; Miyasaka, T. Chem.Pharm. Bull. 1994, 42, 2518.
27. (a) Scudiero, D. A.; Shoemaker, R. H.; Paull, K. D.; Monks, A.; Tieney, S; Hafziget, T. H.; Currens, J. J.; Chou, T. C.; Wu, T. S.;Sheriff, D.; Boyd, M. R. Cancer Res. 1988, 48, 4827.
28. (b) Tseng, C. C.; Watanabe, K. A.; Su, T. L. Phytotherapy Res. 1989, 3, 237.
29. Skehan, P.; Storeng, R; Scudiero, D; Monks, A; McMahon, J.; Vistica, D; Warren, J. T.; Bokesch, H.; Kenny, S.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 1107.
30. Chou, J.; Chou, T. C. Dose-effect analysis with microcomputers. 2nd ed., Biosoft, Cambridge, U.K. 1987.
31. Hsiang, Y.-H.; Hertzberg, S. H.; Liu, L. F. J. Biol. Chem. 1985, 260, 14873.
32. Liu, L. F.; Thomas, C. R.; Yang, L.; Tewey, K. M.; and Chen, G. L. J. Biol. Chem. 1980, 258, 15365-.
33. 6 cells were inoculated subcutaneously on day-3. Average tumor volumes were described as the ratio of treated versus the untreated control (T/C).