Segall Y, Kimmel E C, Dohn D R, Casida J E
Mutat Res. 1985 Oct-Nov;158(1-2):61-8. doi: 10.1016/0165-1218(85)90098-9.
The mutagenicity of halopropenals for Salmonella typhimurium strain TA100 is as follows (revertants/nmole): 2-halopropenals [H2C = C(X)CHO], F = less than 0.6, Cl = 135, Br = 1140 and I = less than 2.4; 3-substituted-2-halopropenals [CH3CH = C(X)CHO], Cl = 68 and Br = 108; [C6H5CH = C(X)CHO], Cl = less than 1 and Br = 5; [ClCH = C(Cl)CHO], 91; [CH3(CH2)2CH = C(Br)CHO], less than 1; [(CH3)2C = C(Br)CHO], less than 0.5. Each of the active compounds is detoxified by the liver S9 fraction. Glutathione also detoxifies the 2-halopropenals and 2-halobutenals, more rapidly for the bromo than the chloro analogs. The mutagenic potency on metabolic activation of the herbicide diallate by microsomes or the S9 fraction is attributable to approximately 50% conversion to 2-chloropropenal when corrected for detoxification in these systems or with GSH. There is no correlation between mutagenicity and reactivity with the model thiol, 4-nitrobenzenethiol. The mutagenicity of 2,3-dichloro- and 2,3-dibromo-propanals and the corresponding dihalobutanals is accounted for by their rapid dehydrohalogenation to the corresponding 2-haloalkenals under physiological conditions. Chemicals that are metabolized to 2,3-dichloropropanal, 2,3-dichlorobutanal, their dibromo analogs, or to the corresponding 2-halopropenals and 2-halobutenals should therefore be considered as candidate promutagens.
卤代丙烯醛对鼠伤寒沙门氏菌TA100菌株的致突变性如下（回复突变体数/纳摩尔）：2-卤代丙烯醛[H2C = C(X)CHO]，F＜0.6，Cl = 135，Br = 1140，I＜2.4；3-取代-2-卤代丙烯醛[CH3CH = C(X)CHO]，Cl = 68，Br = 108；[C6H5CH = C(X)CHO]，Cl＜1，Br = 5；[ClCH = C(Cl)CHO]，91；[CH3(CH2)2CH = C(Br)CHO]，＜1；[(CH3)2C = C(Br)CHO]，＜0.5。每种活性化合物都可被肝脏S9组分解毒。谷胱甘肽也可使2-卤代丙烯醛和2-卤代丁烯醛解毒，对溴代类似物的解毒速度比对氯代类似物快。在这些系统中或使用谷胱甘肽校正解毒作用后，除草剂燕麦敌经微粒体或S9组分代谢活化后的致突变能力约50%归因于其转化为2-氯丙烯醛。致突变性与与模型硫醇4-硝基苯硫酚的反应性之间无相关性。2,3-二氯丙醛和2,3-二溴丙醛以及相应的二卤代丁醛的致突变性是由于它们在生理条件下迅速脱卤化氢生成相应的2-卤代烯醛。因此，代谢生成2,3-二氯丙醛、2,3-二氯丁醛、它们的二溴类似物或相应的2-卤代丙烯醛和2-卤代丁烯醛的化学物质应被视为潜在的前诱变剂。
