代谢
肠道细菌和肝脏的偶氮还原酶能够将偶氮染料还原,产生相应的芳香胺。基于联苯胺和联苯胺同类物的偶氮染料因其广泛使用以及联苯胺对人类的已知致癌性而受到特别关注。基于β-二酮偶联组分的偶氮染料优先以互变异构的腙形式存在。合成并表征了一系列基于联苯胺和联苯胺同类物的腙染料,通过核磁共振和紫外-可见光谱进行了分析。这些染料使用修改的 Ames 试验进行了致突变性测试,与真正的偶氮染料不同,它们没有显示出显著的致突变活性。腙染料对添加了 FMN 的仓鼠肝脏线粒体后上清液(S-9)的酶促还原具有抗性;在相同条件下,偶氮染料如台盼蓝被迅速还原。
Enteric bacterial and hepatic azoreductase enzymes are capable of reducing azo dyes to yield the constituent aromatic amines. Azo dyes based on benzidine and benzidine congeners have received particular attention because of their widespread use and the known carcinogenicity of benzidine to humans. Azo dyes based on beta-diketone coupling components exist preferentially as the tautomeric hydrazones. A series of hydrazone dyes based on benzidine and benzidine congeners was prepared and characterized by NMR and UV-visible spectroscopy. These dyes were tested for mutagenicity using a modified Ames assay and, unlike the true azo dyes, showed no significant mutagenic activity. The hydrazone dyes were resistant to enzymatic reduction by FMN-supplemented hamster-liver post-mitochondrial supernatant (S-9); under identical conditions, azo dyes such as trypan blue were rapidly reduced.
来源:Hazardous Substances Data Bank (HSDB)