Synthesis and bacterial mutagenicity of the cyclopenta oxides of the four cyclopenta-fused isomers of benzanthracene.
Synthesis and bacterial mutagenicity of the cyclopenta oxides of the four cyclopenta-fused isomers of benzanthracene.
复制标题
苯并蒽的四种环五稠合异构体的环五氧化物的合成和细菌致突变性。
DOI：
10.1093/mutage/2.2.101
复制
发表时间：
1987
期刊：
影响因子：
2.7
通讯作者：
Gold,A
中科院分区：
文献类型：
--
作者：
Bartczak,AW;Sangaiah,R;Ball,LM;Warren,SH;Gold,A
许多含有周边稠合的环戊二烯并环的多环芳烃被认为主要通过环戊二烯并环的环氧化来活化。以环戊二烯并苯并蒽衍生物为原料，通过溴代醇和脱溴化氢反应合成了一系列环戊二烯并苯并蒽环氧化物，分别为苯并[e]乙酰蒽烯-5，6-氧化物、苯并[j]乙酰蒽烯-1，2-氧化物、苯并（l）蒽烯-1，2-氧化物和苯并[k]乙酰菲蒽烯-4，5-氧化物，并用u. v. −维斯和1H n.m.r.光谱学和质谱学。在鼠伤寒沙门氏菌菌株TA 98的艾姆斯平板掺入试验中研究了这些化合物的致突变性。所有氧化物在无外源性代谢活化的情况下均具有活性（170-320 His+回复突变体/纳摩尔），并且在0.5 μg/平板以上也具有毒性。添加S9蛋白并没有增加，一般降低，氧化物的致突变性，而毒性基本不变。这些结果与环戊氧化物作为艾姆斯试验中母体化合物致突变性的主要贡献者的假定作用一致。
Many polycyclic aromatic hydrocarbons containing peripherally fused cyclopenta rings are believed to be activated primarily by epoxidation of the cyclopenta ring. The cyclopenta epoxides of a series of four cyclopenta benzanthracene derivatives, benz[e]aceanthrylene-5,6-oxide, benz[j]ace-anthrylene-1,2-oxide, benz(l)anthrylene-1,2-oxide and benz[k]acephenaceanthrylene-4,5-oxide were synthesized from their parent hydrocarbons by formation of the bromohydrin followed by dehydrobromination, and characterized by u.v. − vis, and1H n.m.r. spectroscopy and mass spectrometry. The mutagenicity of these compounds was investigated in the Ames plate incorporation assay withSalmonella typhimuriumstrain TA98. All the oxides were active without exogenous metabolic activation (170–320 His+revertants per nanomole) and also toxic above 0.5 μg/plate. Addition of S9 protein did not increase, and generally decreased, the mutagenicity of the oxides, while toxicity was largely unchanged. These results are consistent with the postulated role of cyclopenta oxides as major contributors to the mutagenicity of the parent compounds in the Ames assay.