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Gossypol Prototype of Inhibitors Targeted to Dinucleotide Folds

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Abstract:

Gossypol, a disesquiterpene from cottonseed, exhibits multiple biological properties, including male antifertility activity and anticancer activity. Gossypol also inhibits the growth of numerous parasitic organisms and shows antiviral activity against a number of enveloped viruses, including the AIDS virus. Derivatives of gossypol, in which the aldehyde functional groups that contribute to toxicity have been modified, retain or even show enhanced biological activity. Ring substituted 2,3-dihydroxy- 1-naphthoic acids, which are structural analogs of gossypol, share with gossypol the ability to complex with dehydrogenases at the dinucleotide fold (Rossmann fold) with selectivity, suggesting that gossypol may be considered the prototype of a new class of drugs targeted to dehydrogenases. Most of the biological activities of gossypol and related compounds may result from inhibition of dehydrogenases.

Keywords: De Novo synthesis; IR Spectrum; NMR spectroscopy; acetic acid complex; american trypanosomiasis; antispernatigenic activity; cofactor binding; competive inhibitors of NAD H; crystalline hexaacetate; dihydroxynahthalenes; dinucleotide folds; gossylic iminolactone; gossylic lactone; gossypol; human immunodeficiency; hydrophobic residues; mammalian LDH; methlmagnesium bromide; multidrug resistant cells; oxazoline based chemistry; parasite lactate; perl acylated nitriles

Document Type: Review Article

DOI: http://dx.doi.org/10.2174/0929867003375119

Publication date: April 1, 2000

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  • Current Medicinal Chemistry covers all the latest and outstanding developments in medicinal chemistry and rational drug design. Each issue contains a series of timely in-depth reviews written by leaders in the field covering a range of the current topics in medicinal chemistry. Current Medicinal Chemistry is an essential journal for every medicinal chemist who wishes to be kept informed and up-to-date with the latest and most important developments.
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