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Paper | Regular issue | Vol 29, No. 10, 1989, pp.1915-1922
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5049
■ Synthesis and Biological Evalution of Methylated Derivatives of the Cooked Food Mutagen Metabolite 2-Amino-3,6-dihydro-3-methyl-7H-imidazo[4,5-f]quinolin-7-one (7-OH-IQ)

Mohammad Bashir, David G. I. Kingston,* 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

The major anaerobic metabolite of the potent cooked food mutacarcinogen IQ is the oxidised product 7-OH-IQ,which is itself a powerful direct-acting mutagen. The O-methyl and N-methyl derivatives of 7-OH-IQ have been prepared to determine whether the tautomeric form of 7-OH-IQ plays any role in its bioactivity. Both N-methyl 7-OH-IQ and O-methyl 7-OH-IQ show comparable mutagenicity when tested directly against the T98 strain of S. typhimurium, indicating that the quinolone structure does not play a major role in the mutagenicity of 7-OH-IQ. Neither 7-OH-IQ nor the methylated derivatives cleaved DNA in the presence of metal cations.