Oxidative metabolism of 7-methylbenz[a]anthracene, 12-methylbenz[a]anthracene and 7,12-dimethylbenz[a]anthracene by rat liver cytosol.
Earlier studies from this laboratory demonstrated that benz[a]anthracene (BA), 7-methylbenz[a]anthracene (7-MBA) and 12-methylbenz[a]anthracene (12-MBA) undergo a bio-alkylation substitution reaction in the meso-anthracenic position(s) or L-region leading to the biosynthesis of the potent carcinogen 7,12-dimethylbenz[a]anthracene (7,12-DMBA). These results support the hypothesis that for most, if not all, unsubstituted polycyclic aromatic hydrocarbon carcinogens, the chemical or biochemical introduction of an alkyl group in the meso-anthracenic position(s) or L-region is a structural requirement for strong carcinogenic activity. Here we report that the L-region methyl derivatives 7-MBA, 12-MBA and 7,12-DMBA are oxidized to hydroxymethyl derivatives by a rat liver cytosol preparation without any apparent oxidation of the ring positions.
D015127:9,10-Dimethyl-1,2-benzanthracene / Q000378:metabolism*; D000818:Animals; D001551:Benz(a)Anthracenes / Q000378:metabolism*; D003600:Cytosol / Q000378:metabolism*; D005260:Female; D066298:In Vitro Techniques; D008099:Liver / Q000378:metabolism*; D010084:Oxidation-Reduction; D051381:Rats; D011919:Rats, Inbred Strains
D001551:Benz(a)Anthracenes; D015127:9,10-Dimethyl-1,2-benzanthracene; C021220:12-methylbenzanthracene; C021219:7-methylbenzanthracene