Instituto de Ciencias Quimicas, Facultad de Ciencias, Universidad Austral de Chile, Las encinas 220, Valdivia, Chile.
J Mol Model. 2013 Jun;19(6):2573-82. doi: 10.1007/s00894-013-1799-7. Epub 2013 Mar 6.
Registered by the World Health Organization (WHO), 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) is one of the strongest bacterial mutagens ever tested, as highlighted by the Ames Salmonella typhimurium TA100 assay. We provide new insights concerning this mutagenic activity on the basis of global and local theoretically defined electrophilicity indices. Our results further support the idea that mutagenicity of MX and its analogues is related more closely to one-electron transfer processes from the electron-rich biological environment than to adduct formation processes. We also stress that, although the Z-open tautomers are intrinsically more electrophilic than furanone ring analogues, the observed mutagenic activity is significantly correlated only to the electrophilicity response of the ring forms. In that context, we also emphasize that it is electrophilicity at the C α in the α-β unsaturated carbonyl moiety that exhibits a strong correlation with the observed mutagenic activity.
世界卫生组织（WHO）注册的 3-氯-4-（二氯甲基）-5-羟基-2（5H）-呋喃酮（MX）是迄今为止测试过的最强细菌诱变剂之一，这一点在艾姆斯沙门氏菌伤寒 TA100 检测中得到了强调。我们根据全球和局部理论定义的亲电性指数提供了有关这种诱变活性的新见解。我们的研究结果进一步支持了这样一种观点，即 MX 及其类似物的诱变活性与其说是与加合物形成过程有关，不如说是与来自富电子生物环境的单电子转移过程有关。我们还强调，尽管 Z-开式互变异构体在本质上比呋喃酮类似物更具亲电性，但观察到的诱变活性仅与环形式的亲电性响应显著相关。在这种情况下，我们还强调，在α-β 不饱和羰基部分的 Cα 上的亲电性与观察到的诱变活性有很强的相关性。
