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Science 17 April 1970:
Vol. 168. no. 3929, pp. 376 - 378
DOI: 10.1126/science.168.3929.376
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Articles

Reactions of Alpha Methylene Lactone Tumor Inhibitors with Model Biological Nucleophiles

S. Morris Kupchan 1, Dyral C. Fessler 1, M. Allan Eakin 1, and Thomas J. Giacobbe 1

1 Department of Pharmaceutical Chemistry, University of Wisconsin, Madison 53706

Thiols are the most reactive nucleophilic reagents among the biological models investigated. They undergo "Michael-type" addition to the polyfunctional sesquiterpene lactones. The rapid rates of reaction with L-cysteine were measured and the reaction products were characterized. Each addition of thiol successively decreased the cytotoxicity of the adducts formed.


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Science. ISSN 0036-8075 (print), 1095-9203 (online)