Garner R C, Nutman C A
Mutat Res. 1977 Jul;44(1):9-19. doi: 10.1016/0027-5107(77)90110-5.
A series of ten azo dyes as well as various single ring aromatic amines substituted on the benzene ring were tested for bacterial mutagenicity with Salmonella typhimurium TA 1538 using a soft-agar overlay method. Two dyes, sudan 2 and chrysoidin induced mutation but only in the presence of a rat liver preparation. Chrysoidin was the more active. Testing of its reduction products, aniline and 1,2,4-triaminobenzene showed a liver metabolite of the latter compound could be responsible for the mutagenic effect, having a comparable mutagenicity with 1,2-diamino-4-nitro-benzene, one of the mutagenic constituents of hair dyes. Structure-activity studies on a series of ring-substituted anilines indicated that mutagenic activity required at least two positions to be substituted with either amino or nitro groups, or one of each. The bacteria as well as the liver enzyme preparation may partake in the activation of these chemicals. The correlation between mutagenicity and carcinogenicity for this group of compounds is discussed.
采用软琼脂覆盖法,用鼠伤寒沙门氏菌TA 1538对一系列十种偶氮染料以及苯环上带有各种单环芳香胺进行细菌诱变性测试。两种染料,苏丹2和金胺可诱导突变,但仅在存在大鼠肝脏制剂的情况下。金胺活性更强。对其还原产物苯胺和1,2,4-三氨基苯的测试表明,后一种化合物的肝脏代谢产物可能是诱变作用的原因,其诱变性与染发剂的诱变成分之一1,2-二氨基-4-硝基苯相当。对一系列环取代苯胺的构效关系研究表明,诱变活性至少需要两个位置被氨基或硝基取代,或各取代一个。细菌以及肝脏酶制剂可能参与这些化学物质的活化。讨论了这组化合物的诱变性与致癌性之间的相关性。