Studies on Carcinogenic Azo Dyes. VI. Effect of Factors Influencing Drug Metabolism on the NIH Shift during Hydroxylations of 4-Dimethylamino-3'-methylazobenzene and 3-Methylacetanilide

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The NIH shift during aryl hydroxylations of 4-dimethylamino-3'-methylazobenzene (3'-Me-DAB) and 3-methylacetanilide under various conditions has been investigated. 4-Hydroxy-3-methylacetanilide was obtained from 3-methylacetanilide (4-^2H, or 4-^3H) by rat in vivo metabolism or by incubation with hepatic microsomal preparations of rat, mouse, hamster, or rabbit, and 3'-Me-4'-hydroxy-DAB by incubation of 3'-Me-DAB (4'-^3H, or 4'-^8H) with the liver homogenates. Retention of heavy hydrogen in the hydroxylated products was determined by mass spectrometry or liquid scintillation counting. The degree of retention of isotopic hydrogen during hydroxylation of the labeled 3-methylacetanilide was affected by the pH of incubation media, the species variation, the sex of animal used as the source of microsomal preparations, and the pretreatment of animal with inducing agents. Pretreatment of rat or mouse with phenobarbital caused an increase in the retention of tritium in 4-hydroxy-3-methylacetanilide produced from 3-methylacetanilide-4-^3H, while pretreatment with 3-methylcholanthrene or 3,4-benzpyrene caused a decrease in the retention. Pretreatment of rat with the carcinogenic azo dye, 3'-Me-DAB, did not affect the NIH shift during the in vivo hydroxylation of 3-methylacetanilide-4-^2H. The effect of induction on the retention of tritium or deuterium is unique to 3-methylacetanilide (4-^2H, or 4-^3H), and is not observed during hydroxylation of 3'-Me-DAB (4'-^2H, or 4'-^3H) in which the tritium retention is also independent on the pH of incubation media and the species.
1976-03-25

Studies on Carcinogenic Azo Dyes. VI. Effect of Factors Influencing Drug Metabolism on the NIH Shift during Hydroxylations of 4-Dimethylamino-3'-methylazobenzene and 3-Methylacetanilide

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