6533b81ffe1ef96bd127885d

RESEARCH PRODUCT

Metabolic epoxidation of trans-4-acetylaminostilbene: A protective mechanism against its activation to a mutagen

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description

Abstract Trans -4-acetylaminostilbene is activated by liver preparations to mutagens for Salmonella typhimurium . Since this compound is metabolized to the trans -α,β-epoxide and since many epoxides are ultimate mutagens, this epoxide was tested for direct mutagenicity. It was, however, found to be non-mutagenic, and, in contrast to the parent compound, the epoxide was no longer activated by liver preparations to mutagens. The same was found for the β-ketone and for the threo -α,β-dihydrodiol, which are formed metabolically from trans -4-acetylaminostilbene and from its α,β-epoxide. 4-Acetylaminobibenzyl showed a very weak mutagenic activity in the presence of the liver preparation. Thus, it is important to realize that where epoxides are formed from compounds which are known to be metabolized to mutagens, they are not necessarily responsible for the mutagenicity. Epoxidation may even prevent the possibility of bioactivation to mutagens.