Eder E, Deininger C, Deininger D, Weinfurtner E
Institute of Pharmacology and Toxicology, University of Würzburg, Germany.
Mutat Res. 1994 Oct;322(4):321-8. doi: 10.1016/0165-1218(94)90108-2.
2-Chloroacrolein and 2-bromoacrolein are very potent direct mutagens not requiring metabolic activation in Salmonella typhimurium strains TA 100 and TA 1535. Mutagenic activities decrease with increasing degree of methyl substitution at carbon atom C-3 of the acrolein moiety from 2-chloroacrolein via 2-chlorocrotonaldehyde to 2-chloro-3,3-dimethylacrolein. With 2-chloroacrylonitrile equivocal results are obtained in strain TA 100 without S9-mix and unequivocal with S9-mix. In the SOS-chromotest the 2-chloroenals are also very strong genotoxins and the structure-activity relationships found in the Ames test are clearly confirmed. 2-Chloroacrylonitrile is not positive in the SOS-chromotest. The mutagenic mechanisms are discussed, and indications are provided that genotoxicity/mutagenicity depends on formation of DNA adducts, e.g., 1,N2-cyclic deoxyguanosine adducts.
2-氯丙烯醛和2-溴丙烯醛是非常强效的直接诱变剂，在鼠伤寒沙门氏菌TA 100和TA 1535菌株中不需要代谢活化。从2-氯丙烯醛经2-氯巴豆醛到2-氯-3,3-二甲基丙烯醛，随着丙烯醛部分C-3碳原子甲基取代程度的增加，诱变活性降低。对于2-氯丙烯腈，在无S9混合液的TA 100菌株中结果不明确，而在有S9混合液时结果明确。在SOS-显色试验中，2-氯烯醛也是非常强的基因毒素，并且在艾姆斯试验中发现的构效关系得到了明确证实。2-氯丙烯腈在SOS-显色试验中呈阴性。文中讨论了诱变机制，并指出遗传毒性/诱变性取决于DNA加合物的形成，例如1,N2-环化脱氧鸟苷加合物。
