ELECTROPHILIC REACTIVITY AND MUTAGENICITY OF RING-METHYL DERIVATIVES OF N-ACYLOXY-N-METHYL-4-AMINOAZOBENZENE AND RELATED AZO DYES

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  • Electrophilic Reactivity and Mutagenici

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As the prototypes for proximate and ultimate metabolite of hepatocarcinogenic N-methyl-4-aminoazobenzene (MAB) dyes, N-hydroxy and N-acyloxy derivatives were synthesized from MAB, 3'-methyl-MAB, and 4'-methyl-MAB, whose carcinogenic activities in the rat are known to be quite different, and electrophilic reactivity and mutagenicity of the parent dyes and the N-hydroxy and N-acyloxy derivatives were comparatively studied. MAB and its ring-methyl derivatives did not show reactivity with amino acids, proteins, or with DNA, and N-hydroxy derivatives reacted a little except with cysteine. Mutagenicity of these dyes towards Salmonella typhimurium TA-98 and TA-100 was expressed only in the presence of 9000g supernatant of a rat liver homogenate (S-9 Mix), and either 3'-methyl or 4'-methyl substituent did not affect the mutagenic activity of the parent dyes. By contrast, N-acetoxy-MAB, N-benzoyloxy-MAB, and their ring-methyl derivatives showed a high degree of reactivity with amino acids, proteins, and DNA, and they were strongly mutagenic towards the bacteria without S-9 Mix treatment. No critical differences were observed among these N-acyloxy derivatives either in their electrophilic reactivity or mutagenicity.<br>These findings suggest that neither the rate of metabolic activation by liver enzymes from MAB homologs to the ultimate metabolite nor electrophilic or mutagenic activity of the prototype compounds for the ultimate metabolite is influenced by the ring-methyl substituent which affects the carcinogenic activity of the parent dyes. Other possible factors influencing the carcinogenic activity of MAB homologs are discussed.

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