Coles B, Ketterer B, Beland F A, Kadlubar F F
Carcinogenesis. 1984 Jul;5(7):917-20. doi: 10.1093/carcin/5.7.917.
The presumed ultimate carcinogenic metabolite of the rat hepatocarcinogen N-methyl-4-aminoazobenzene (MAB), N-sulphonyloxy-MAB, was synthesized and reacted with glutathione (GSH) to yield the stable ring-substituted conjugates, 3-, 2'- and 4'-glutathion-S-yl-MAB (3-, 2'- and 4'-GSMAB) and the unstable methylene-substituted conjugate, N-(glutathion-S-methylene)-4-aminoazobenzene. Reaction of the model ultimate carcinogen, N-benzoyloxy-MAB, or the proximate carcinogen, N-hydroxy-MAB, with GSH also gave the same four conjugates. The ratio of ring-substitution relative to methylene conjugate formation increased with stronger leaving groups; i.e., ring-substitution increased in the order: N-hydroxy: N-benzoyloxy: N-sulphonyloxy. The ratio of 3-GSMAB to 2'- plus 4'-GSMAB was constant for all three MAB derivatives.
大鼠肝癌致癌物N-甲基-4-氨基偶氮苯（MAB）的假定最终致癌代谢物N-磺酰氧基-MAB被合成，并与谷胱甘肽（GSH）反应，生成稳定的环取代缀合物3-、2'-和4'-谷胱甘肽-S-基-MAB（3-、2'-和4'-GSMAB）以及不稳定的亚甲基取代缀合物N-（谷胱甘肽-S-亚甲基）-4-氨基偶氮苯。模型最终致癌物N-苯甲酰氧基-MAB或近似致癌物N-羟基-MAB与GSH反应也得到相同的四种缀合物。随着离去基团增强，环取代相对于亚甲基缀合物形成的比例增加；即环取代按以下顺序增加：N-羟基：N-苯甲酰氧基：N-磺酰氧基。对于所有三种MAB衍生物，3-GSMAB与2'-加4'-GSMAB的比例是恒定的。
