Mutagenic and DNA-damaging effects of N-(omega-acetoxyalkyl and omega-methoxycarbonylalkyl)-N-(alpha-acetoxyalkyl)nitrosamines, models for metabolically activated N,N-dialkylnitrosamines with an omega-functional group.

Abstract

Mutagenic and DNA-damaging effects of a series of N,N-dialkylnitrosamines having an alpha-acetoxy group together with an alpha-acetoxy or an omega-methoxycarbonyl group were tested in Salmonella typhimurium, Escherichia coli, and Bacillus subtilis without metabolic activation. The compounds comprised each of 3 N-(omega-acetoxyalkyl)-N-(acetoxymethyl)nitrosamines, N-(omega-methoxycarbonylalkyl)-N-(acetoxymethyl)nitrosamines, and N-(omega-methoxycarbonylalkyl)-N-(alpha-acetoxybutyl)nitrosamines. All the compounds gave positive results in these mutagenicity and repair tests. No definite differences were observed in the mutagenic and DNA-damaging effects between the model compounds derived from the carcinogenic compounds and those derived from the non-carcinogenic counterparts. The strongest mutagenic activity was observed so far with N-(2-methoxycarbonylethyl)-N-(l-acetoxybutyl)nitrosamine in all of the four bacterial strains.