Modification of the Hydroxy Lactone Ring of Camptothecin: Inhibition of Mammalian Topoisomerase I and Biological Activity

Journal of Medicinal Chemistry

Volumn 32, Issue 3, 1989, Pages 715-720

  Hertzberg, Robert P ^a   Caranfa, Mary Jo ^a   Holden, Kenneth G ^a   Jakas, Dalia R ^a   Gallagher, Gregory ^a   Mattern, Michael R ^a   Mong, Shau ming ^a   Bartus, Joan O'leary ^a   Johnson, Randall K ^a   Kingsbury, William D ^a  

^a SmithKline Beecham   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPTOTHECIN DERIVATIVE; DNA TOPOISOMERASE;

ANIMAL CELL; CELL CULTURE; CYTOTOXICITY; DRUG SYNTHESIS; MASS SPECTROMETRY; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ANIMAL; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CAMPTOTHECIN; CHEMISTRY; DNA TOPOISOMERASES, TYPE I; DRUG SCREENING ASSAYS, ANTITUMOR; LEUKEMIA L1210; MICE; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0024537205     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00123a038     Document Type: Article

References (20)

1. Wall, M. E.; Wani, M. C.; Cook, C. E.; Palmer, K. H.; McPhail, A. T.; Sim, G. A. J. Am. Chem. Soc. 1966, 88, 3888.
2. Suffness, M.; Cordell, G. A. In The Alkaloids: Chemistry and Pharmacology; Brossi, A. Ed.; Academic Press: Orlando, FL, 1985; Vol. 25, p 73.
3. Hsiang, Y. H.; Hertzberg, R.; Hecht, S.; Liu, L. F. J. Biol. Chem. 1985, 260, 14873.
4. Thomsen, B.; Mollerup, S.; Bonven, B. J.; Frank, R.; Blocker, H.; Nielsen, O. F.; Westergaard, O. EMBO J. 1987, 6, 1817.
5. Hertzberg, R. P.; Holden, K. G.; Hecht, S. M.; Mattern, M. R.; Faucette, L. F.; Johnson, R. K. Proc. Am. Assoc. Cancer Res. 1987, 28, 27.
6. Mattern, M. R.; Mong, S. M.; Bartus, H. F.; Mirabelli, C. K.; Crooke, S. T.; Johnson, R. K. Cancer Res. 1987, 47, 1793.
7. Horwitz, S. B. In Antibiotics III. Mechanism of Action of Antimicrobial and Antitumor Agents; Corcoran, J. W., Hahn, F. E., Eds.; Springer: New York, 1975; p 48.
8. Andoh, T.; Ishii, K.; Suzuki, Y.; Ikegami, Y.; Kusunoki, Y.; Takemoto, Y.; Okada, K. Proc. Natl. Acad. Sci. U. S. A. 1987, 84, 5565. (b) Kjeldsen, E.; Bonven, B.; Andoh, T.; Ishii, K. Okada, K.; Bolund, L.; Westergaard, O. J. Biol. Chem. 1988, 263, 3912.
9. Gupta, R. S.; Gupta, R.; Eng, B.; Lock, R. B.;,Ross, W. E.; Hertzberg, R. P.; Caranfa, M. J.; Johnson, R. K. Cancer Res. 1988, 48. 6404.
10. Wall, M. E.; Wani, M. C. Annu. Rev. Pharmacol. Toxicol. 1977, 17, 117.
11. Adamovics, J. A.; Hutchinson, C. R. J. Med. Chem. 1979, 22, 310. (b) Hutchinson, C. R. Tetrahedron 1981, 37, 1047.
12. Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 7026.
13. Lown, J. W.; Chen, H. H. Biochem. Pharmacol. 1980, 29.,905.
14. Mappicine ketone 13 was prepared by treating camptothecin with NaN3 (Kingsbury, W. Tetrahedron Lett., in press).
15. Drewes, S. E.; Loiyou, G.; Roos, G. H. P. Synth. Commun. 1987, 17, 291.
16. Wani, M. C.; Ronman, P. E.; Lindley, J. T.; Wall, M. E. J. Med. Chem. 1980, 23, 554.
17. Wall, M. E. Biochem. Physiol. Alkaloid Int. Symp. 4th 1969, 77.
18. Pommier, Y.; Jaxel, C.; Covey, J. M.; Kerrigan, D.; Wani, M. C.; Wall, M. E.; Kohn, K. W. Proc. Am. Assoc. Cancer Res. 1988. 29. 1080.
19. Wani, M. C.; Nicholas, A. W.; Wall, M. E. J. Med. Chem. 1987, 30, 2317.
20. Liu, L. F. Methods Enzymol. 1983, 100, 133.