Ketterer B, Kadlubar F, Flammang T, Carne T, Enderby G
Chem Biol Interact. 1979 Apr;25(1):7-21. doi: 10.1016/0009-2797(79)90065-6.
N-Benzoyloxy-N-methyl-4-aminoazobenzene (N-BzO-MAB) is believed to be an analogue of the ultimate carcinogenic form of N,N-dimethyl-4-aminoazobenzene (DAB). The reaction of N-BzO-MAB with glutathione in vitro yielded one major and two minor aminoazo dye-glutathione adducts. After purification by ion exchange chromatography and high pressure liquid chromatography, analysis of chemical properties, and the measurement of ultraviolet, visible, proton magnetic resonance, and mass spectra, the major and one minor adduct were identified as 3-(glutathion-S-yl)-N-methyl-4-aminoazobenzene (3-GS-MAB) and 2'-(glutathion-S-yl)-N-methyl-4-aminoazobenzene (2'-GS-MAB) respectively. The other minor adduct was tentatively identified as 4'-(glutathion-S-yl)-N-methyl-4-aminoazobenzene (4'-GS-MAB). Fractionation and analyses of biliary metabolites from rats given DAB revealed the presence of two aminoazo dye-glutathione adducts. One of these was identical to 3-GS-MAB in its chromatographic and chemical properties and its visible and ultraviolet spectra. The other adduct was partially characterized and judged to be a 4-aminoazobenzene-glutathione adduct. The role of glutathione in the detoxification of carcinogenic aminoazo dyes is discussed.
N-苯甲酰氧基-N-甲基-4-氨基偶氮苯（N-BzO-MAB）被认为是N，N-二甲基-4-氨基偶氮苯（DAB）最终致癌形式的类似物。N-BzO-MAB与谷胱甘肽在体外反应产生了一种主要的和两种次要的氨基偶氮染料-谷胱甘肽加合物。通过离子交换色谱法和高压液相色谱法纯化、化学性质分析以及紫外、可见、质子磁共振和质谱测量后，主要加合物和一种次要加合物分别被鉴定为3-（谷胱甘肽-S-基）-N-甲基-4-氨基偶氮苯（3-GS-MAB）和2'-（谷胱甘肽-S-基）-N-甲基-4-氨基偶氮苯（2'-GS-MAB）。另一种次要加合物被初步鉴定为4'-（谷胱甘肽-S-基）-N-甲基-4-氨基偶氮苯（4'-GS-MAB）。对给予DAB的大鼠胆汁代谢产物进行分级分离和分析，发现存在两种氨基偶氮染料-谷胱甘肽加合物。其中一种在色谱和化学性质以及可见和紫外光谱方面与3-GS-MAB相同。另一种加合物进行了部分表征，判断为4-氨基偶氮苯-谷胱甘肽加合物。讨论了谷胱甘肽在致癌性氨基偶氮染料解毒中的作用。
