Bolt H M
Institute of Occupational Health, University of Dortmund, Federal Republic of Germany.
Crit Rev Toxicol. 1988;18(4):299-309. doi: 10.3109/10408448809037469.
Cyclic DNA adducts bearing an "etheno" structure have been described to occur after interaction with metabolites of halogenated olefins. Extensive work has been published on adducts of vinyl chloride, both in vitro and in vivo. The major DNA adduct of vinyl chloride is 7-(2-oxoethyl)guanine, but an important minor adduct appears to be N2,3-ethenoguanine. Other etheno adducts, i.e., 1, N6-ethenoadenine and 3, N4-ethenocytosine, are readily formed with DNA, vinyl chloride, and a metabolizing system in vitro and with RNA in vivo, but usually are not detected as DNA adducts in vivo. Other compounds that have been studied with respect to possible formation of etheno DNA adducts are vinyl bromide (which is more or less completely analogous to vinyl chloride), acrylonitrile, vinyl acetate and vinyl carbamate. Proposals of possible structures of DNA adducts with an etheno structure have been promutagenic potential of these lesions which may lead to misincorporation of wrong DNA bases in newly synthesized DNA.
据描述，带有“乙烯基”结构的环状DNA加合物是在与卤代烯烃的代谢产物相互作用后出现的。关于氯乙烯的加合物，已经发表了大量体外和体内研究的工作。氯乙烯的主要DNA加合物是7-(2-氧代乙基)鸟嘌呤，但一种重要的次要加合物似乎是N2,3-乙烯基鸟嘌呤。其他乙烯基加合物，即1,N6-乙烯基腺嘌呤和3,N4-乙烯基胞嘧啶，在体外可与DNA、氯乙烯和代谢系统轻松形成，在体内可与RNA形成，但在体内通常不会被检测为DNA加合物。关于可能形成乙烯基DNA加合物的其他化合物，也进行了研究，包括溴乙烯（或多或少与氯乙烯完全类似）、丙烯腈、乙酸乙烯酯和乙烯基氨基甲酸酯。具有乙烯基结构的DNA加合物可能结构的提议，这些损伤具有潜在的致突变性，可能导致新合成的DNA中错误的DNA碱基错配掺入。
