Hecht S S, Lin D
Carcinogenesis. 1986 Apr;7(4):611-4. doi: 10.1093/carcin/7.4.611.
4-(Carbethoxynitrosamino)-1-(3-pyridyl)butanal, a stable precursor to the putative diazohydroxide formed by 5'-hydroxylation of the tobacco-specific nitrosamine, N'-nitrosonornicotine, was synthesized in six steps from nicotinaldehyde. Its mutagenicity toward S. typhimurium was compared to that of 4-(carbethoxynitrosamino)-1-(3-pyridyl)-1-butanone, a precursor to the diazohydroxide formed by 2'-hydroxylation of N'-nitrosonornicotine. At equimolar doses, 4-(carbethoxynitrosamino)-1-(3-pyridyl)-1-butanone was a potent mutagen, but 4-(carbethoxynitrosamino)-1-(3-pyridyl)butanal was inactive toward strains TA 100 and TA 1535. The results of this study indicate that the putative diazohydroxide formed by 2'-hydroxylation of N'-nitrosonornicotine has higher inherent mutagenicity toward S. typhimurium than does the corresponding diazohydroxide formed by 5'-hydroxylation.
4-（乙氧羰基亚硝基氨基）-1-（3-吡啶基）丁醛是由烟草特有的亚硝胺N'-亚硝基降烟碱经5'-羟基化形成的假定重氮氢氧化物的稳定前体，它由烟醛经六步合成。将其对鼠伤寒沙门氏菌的诱变性与4-（乙氧羰基亚硝基氨基）-1-（3-吡啶基）-1-丁酮（由N'-亚硝基降烟碱经2'-羟基化形成的重氮氢氧化物的前体）的诱变性进行了比较。在等摩尔剂量下，4-（乙氧羰基亚硝基氨基）-1-（3-吡啶基）-1-丁酮是一种强效诱变剂，但4-（乙氧羰基亚硝基氨基）-1-（3-吡啶基）丁醛对TA 100和TA 1535菌株无活性。这项研究的结果表明，由N'-亚硝基降烟碱经2'-羟基化形成的假定重氮氢氧化物对鼠伤寒沙门氏菌的固有诱变性高于由5'-羟基化形成的相应重氮氢氧化物。
