The mutagenic action of aliphatic epoxides

The mutagenic action of 45 epoxides was investigates in Luria and Delbrück's fluctuation test with Klebsiella pneumoniae as test organism. In this test, 36 of the 45 epoxides appeared to be mutagenic. The mutagenicity of 1,2-epoxides decreased with increasing length of the carbon chain. The mutagenic activity of compounds with a non-terminal epoxide group appeared to be less than that of substances with a terminal one. Generally 1,2-epoxide compounds with electronegative groups were more mutagenic than 1,2-epoxypropane. Of the diepoxides, 1,2,3,4-diepoxybutane appeared to be more mutagenic than 1,2,7,8-diepoxyoctane, while the ring compounds 1,2,5,6-diepoxycyclooctane was hardly mutagenic. The ring compound 4-vinylcyclohexenedioxide, used in electron microscopy that the antibiotic fosfomycin is among the more potent mutagenic substances investigated in this study.