Haugen D A, Peak M J, Reilly C A
Mutat Res. 1981 Jun;82(1):59-67. doi: 10.1016/0027-5107(81)90138-x.
Treatment of mutagenic primary aromatic amines with nitrous acid is known to decrease their mutagenicity. We examined some factors concerning the validity of using decreases in mutagenicity due to nitrous acid treatment as an indication of the presence of mutagenic primary aromatic amines in complex mixtures. We found that treatment of benzo[alpha]pyrene with nitrous acid for the extended periods of time previously employed leads to formation of three nitrobenzo[alpha]pyrene isomers. Some of the isomers are direct-acting mutagens for S. typhimurium with considerably greater mutagenicity than benzo[alpha]pyrene isomers. In attempts to minimize reaction of chemicals other than aromatic amines, we found that only very brief reaction periods are required for complete reaction of nitrous acid with representative aromatic amines, essentially eliminating their mutagenicity. During such brief reaction periods modification of benzo[alpha]pyrene is negligible, but phenols react readily. Chromatographic analysis indicated that reaction of nitrous acid with aromatic amines leads to the formation of families of products, thereby increasing the complexity of the mixtures in which the amines may occur. Thus, experiments examining the effects of nitrous acid on the mutagenic activity of complex mixtures must be carefully designed, and the results must be interpreted cautiously.
已知用亚硝酸处理诱变的伯芳香胺会降低其诱变性。我们研究了一些有关将亚硝酸处理导致的诱变性降低作为复杂混合物中诱变伯芳香胺存在指标的有效性的因素。我们发现，按照之前采用的较长时间用亚硝酸处理苯并[a]芘会导致形成三种硝基苯并[a]芘异构体。其中一些异构体是鼠伤寒沙门氏菌的直接作用诱变剂，其诱变性比苯并[a]芘异构体大得多。为尽量减少芳香胺以外的化学物质的反应，我们发现亚硝酸与代表性芳香胺完全反应只需非常短的反应时间，基本上消除了它们的诱变性。在如此短的反应时间内，苯并[a]芘的改性可忽略不计，但酚类反应很容易。色谱分析表明，亚硝酸与芳香胺反应会导致形成一系列产物，从而增加了胺类可能存在的混合物的复杂性。因此，研究亚硝酸对复杂混合物诱变活性影响的实验必须精心设计，结果也必须谨慎解释。
