Mutagenicity studies of p-substituted benzyl derivatives in the Ames Salmonella plate-incorporation assay.
The mutagenicity of 24 benzyl derivatives, containing a variety of substituents and leaving groups, were assayed in strain TA100 using the Ames plate-incorporation assay. p-Nitrobenzyl chloride (12 000 revertants/mumole), p-nitrobenzyl tosylate (6100 revertants/mumole), and p-acetoxybenzyl chloride (100 revertants/mumole) were mutagenic; none of the remaining 21 compounds were mutagenic. p-Nitrobenzyl chloride was also found to be mutagenic in strain TA98 (700 revertants/mumole), but not in strain TA98NR (a strain deficient in nitro reductase activity). p-Acetoxybenzyl chloride was nonenzymatically hydrolyzed to p-hydroxybenzyl alcohol and p-acetoxybenzyl alcohol. These findings suggest that nitrobenzyl derivatives were mutagenic due to nitro reductive metabolism and that p-acetoxybenzyl chloride was mutagenic due to the intermediate formation of p-hydroxybenzyl chloride during the hydrolysis of p-acetoxybenzyl chloride.
D001593:Benzyl Compounds / Q000494:pharmacology*; D008401:Gas Chromatography-Mass Spectrometry; D006868:Hydrolysis; D009152:Mutagenicity Tests; D009153:Mutagens; D009154:Mutation; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship
D001593:Benzyl Compounds; D009153:Mutagens