Fiala E S, Kohl N E, Hecht S S, Yang J J, Shimada T
Carcinogenesis. 1981;2(3):165-73. doi: 10.1093/carcin/2.3.165.
Incubation of phenylethylamine with rabbit liver microsomes, divalent manganese and a NADPH generating system leads to the formation of azoxy-2-phenylethane, among other metabolic products. Approximately 38 nmol of the azoxy compound is formed form 10 mumol of phenylethylamine during a 30 min incubation. Azoxy-2-phenylethane was identified by comparison of its chromatographic (thin-layer, high pressure liquid and gas chromatography) properties with those of an authentic standard and was confirmed by mass spectrometry. The metabolism of phenylethylamine to azoxy-2-phenylethane appears completely dependent on the presence of divalent manganese; no reaction was observed in the absence of this metal or in the presence of equivalent concentrations of cupric ions. Azoxy-2-phenylethane was mutagenic, with S-9 activation, in S. typhimurium strains TA 100 and TA 1535 but not in TA 98 or TA 1537. This report constitutes the first demonstration of the formation of an aliphatic azoxy compound from the corresponding amine by a mammalian system.
苯乙胺与兔肝微粒体、二价锰以及一个NADPH生成系统一起温育，除了其他代谢产物外，还会生成氧化偶氮-2-苯乙烷。在30分钟的温育过程中，大约38纳摩尔的氧化偶氮化合物由10微摩尔的苯乙胺生成。通过将其色谱（薄层、高压液相和气相色谱）性质与标准品的性质进行比较，鉴定出了氧化偶氮-2-苯乙烷，并通过质谱法进行了确认。苯乙胺代谢生成氧化偶氮-2-苯乙烷的过程似乎完全依赖于二价锰的存在；在没有这种金属或存在等量铜离子的情况下未观察到反应。在有S-9激活剂存在的情况下，氧化偶氮-2-苯乙烷在鼠伤寒沙门氏菌菌株TA 100和TA 1535中具有致突变性，但在TA 98或TA 1537中无致突变性。本报告首次证明了哺乳动物系统可由相应胺生成脂肪族氧化偶氮化合物。
