Mutagenic potential of allyl and allylic compounds: Structure-activity relationship as determined by alkylating and direct in vitro mutagenic properties

Abstract

A series of compounds, each containing an allylic moiety, has been tested using Salmonella typhimurium TA 100 in a modified Ames mutagenicity assay system. In the absence of activating enzymes (S-9) mix, those allylic compounds possessing chemically good leaving groups show direct mutagenic activity. Their activity decreases in the following order: allyl methanesulfonate > -iodide > -bromide > -chloride. This is in good agreement with the alkylating properties measured in the nitrobenzyl-pyridine (NBP) test. For all allyl and allylic compounds found to be directly mutagenic, a decrease in, and sometimes total loss, of mutagenicity is registered after addition of S-9 supernatants. Compared to the direct mutagenic activity of allyl chloride, epichlorohydrin shows a much higher mutagenicity, whereas propyl chloride has proven to be nonmutagenic. The direct mutagenic effect of this type of compound is theoretically explained by sn-1, Sn-2 and SN-2' mechanisms.