Antineoplastic agents. 291. Isolation and synthesis of combretastatins A-4, A-5, and A-6

George Pettit, Sheo Bux Singh, Michael R. Boyd, Ernest Hamel, Robin Pettit, Jean M. Schmidt, Fiona Hogan

Research output: Contribution to journalArticle

358 Citations (Scopus)

Abstract

The antineoplastic constituents of Combretum caffrum (Eckl. and Zeyh) Kuntze (Combretaceae family), a species indigenous to South Africa, have been investigated. Subsequently we isolated a series of closely related bibenzyls, stilbenes, and phenanthrenes from C. caffrum. Some of the stilbenes proved to be potent antimitotic agents which inhibited both tubulin polymerization and the binding of colchicine to tubulin. Combretastatin A-4 has been shown to be the most potent cancer cell growth inhibitor of the series. Presently this cis-stilbene is the most effective inhibitor of colchicine binding to tubulin and the simplest natural product yet described with such potent antitubulin effects. Combretastatin A-4, A-5, and A-6 were also found to inhibit growth of Neisseria gonorrhoeas. Details of the isolation and syntheses of combretastatins A-4 (2a), A-5 (2c), and A-6 (3a) have been described.

Original languageEnglish (US)
Pages (from-to)1666-1672
Number of pages7
JournalJournal of Medicinal Chemistry
Volume38
Issue number10
StatePublished - 1995

Fingerprint

Stilbenes
Tubulin
Antineoplastic Agents
Colchicine
Bibenzyls
Phenanthrenes
Combretum
Combretaceae
Antimitotic Agents
Growth Inhibitors
Neisseria gonorrhoeae
South Africa
Biological Products
Polymerization
Growth
fosbretabulin
Neoplasms

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Pettit, G., Singh, S. B., Boyd, M. R., Hamel, E., Pettit, R., Schmidt, J. M., & Hogan, F. (1995). Antineoplastic agents. 291. Isolation and synthesis of combretastatins A-4, A-5, and A-6. Journal of Medicinal Chemistry, 38(10), 1666-1672.

Antineoplastic agents. 291. Isolation and synthesis of combretastatins A-4, A-5, and A-6. / Pettit, George; Singh, Sheo Bux; Boyd, Michael R.; Hamel, Ernest; Pettit, Robin; Schmidt, Jean M.; Hogan, Fiona.

In: Journal of Medicinal Chemistry, Vol. 38, No. 10, 1995, p. 1666-1672.

Research output: Contribution to journalArticle

Pettit, G, Singh, SB, Boyd, MR, Hamel, E, Pettit, R, Schmidt, JM & Hogan, F 1995, 'Antineoplastic agents. 291. Isolation and synthesis of combretastatins A-4, A-5, and A-6', Journal of Medicinal Chemistry, vol. 38, no. 10, pp. 1666-1672.
Pettit, George ; Singh, Sheo Bux ; Boyd, Michael R. ; Hamel, Ernest ; Pettit, Robin ; Schmidt, Jean M. ; Hogan, Fiona. / Antineoplastic agents. 291. Isolation and synthesis of combretastatins A-4, A-5, and A-6. In: Journal of Medicinal Chemistry. 1995 ; Vol. 38, No. 10. pp. 1666-1672.
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