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■ Isolation, Structure Elucidation, and Synthesis of the Major Anaerobic Bacterial Metabolite of the Dietary Carcinogen 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx)

Mohammad Bashir, David G. I. Kingston,* Robert J. Carman, Roger L. Van Tassell,and Tracy D. Wilkins*

*Department of Chemisry, Virginia Polytecnic Institute and State University, Blacksburg, Virginia 24061-0212, U.S.A.

Abstract

Incubation of the heterocyclic cooked food mutagen 2-amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline (MeIQx, 1) with mixed human fecal microflora under anaerobic conditions yielded 2-amino-3,6-dihydro-3,8-dimethylimidazo[4,5-f]quinoxalin-7-one (7-HOMeIQx, 2), as the major metablite, but with low overall conversion. The metabolite 2 and its isomer 7 have been synthesized. The metabolite 2 is a direct-acting mutagen, but its isomer 7 is non-mutagenic in the absence of metabolic activation.