Stolzenberg S J, Hine C H
J Toxicol Environ Health. 1979 Nov;5(6):1149-58. doi: 10.1080/15287397909529820.
Four structurally related three-carbon compounds, known for their antifertility activity in the male, and the brominated derivatives of two of these compounds were tested for mutagenic activity by the Salmonella typhimurium test of Ames et al. In the presence of strain TA-100, a base-pair substituion detector strain, 1,2-dibromo-3-chloropropane (DBCP), was the most active compound tested but required enzymatic conversion by 59 microsomal preparation to an active mutagen. Three of these compounds containing an epoxide group-epichlorohydrin, epibromohydrin, and glycidol-were highly active direct mutagens, not requiring 59 for activation, alpha-Chlorohydrin was the least active compound tested; alpha-bromohydrin was 40 times more active than its chlorinated analog. Epibromohydrin was only slightly more active than epichlorohydrin, but both were highly active. With both of the halogenated epoxides, 59 preparation caused a substantial decrease in mutagenic activity at every concentration tested. All six compounds showed dose-related responsiveness for the base-pair substitution detector strains used. However, they were relatively inactive against the frameshift detector strain of S. typhimurium, TA-98. Glycerol, propylene glycol, and n-propanol, which are also three-carbon compounds containing one or more hydroxy groups, were inactive when trested at high concentrations with strain TA-100.
四种结构相关的三碳化合物因对雄性动物具有抗生育活性而闻名，其中两种化合物的溴化衍生物通过Ames等人的鼠伤寒沙门氏菌试验检测其致突变活性。在碱基对置换检测菌株TA - 100存在的情况下，1,2 - 二溴 - 3 - 氯丙烷（DBCP）是所测试的最具活性的化合物，但需要通过59种微粒体制剂进行酶促转化才能成为活性诱变剂。这些含有环氧基团的化合物中的三种——环氧氯丙烷、表溴醇和缩水甘油——是高活性的直接诱变剂，不需要59进行激活；α - 氯丙醇是所测试的活性最低的化合物；α - 溴丙醇的活性是其氯化类似物的40倍。表溴醇仅比环氧氯丙烷略具活性，但两者均具有高活性。对于这两种卤代环氧化物，59种制剂在每个测试浓度下均导致诱变活性大幅下降。所有六种化合物对所使用的碱基对置换检测菌株均表现出剂量相关的反应性。然而，它们对鼠伤寒沙门氏菌的移码检测菌株TA - 98相对无活性。甘油、丙二醇和正丙醇也是含有一个或多个羟基的三碳化合物，当用菌株TA - 100在高浓度下测试时无活性。
