A model study of fecapentaenes: mutagens of bacterial origin with alkylating properties.
Fecapentaene-14 and -12 are directly acting mutagens that do not require metabolic activation. Their unusual structure suggests a possible mechanism of action. A carbocation that is formed by the addition of an electrophilic species (such as a proton) to the enol ether is most probably the reactive species. A series of model enol ethers with conjugated systems of various lengths was prepared, and a correlation between mutagenicity and increasing reactivity of derived carbocations was found. The glycerol moiety does not play a crucial role in the overall reactivity of the fecapentaenes.
D000477:Alkylating Agents; D009152:Mutagenicity Tests; D009153:Mutagens / Q000633:toxicity*; D009154:Mutation; D011090:Polyenes / Q000633:toxicity; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship
D000477:Alkylating Agents; D009153:Mutagens; D011090:Polyenes; C037358:1-(1-glycero)tetradeca-1,3,5,7,9-pentaene; C037357:1-(1-glycero)dodeca-1,3,5,7,9-pentaene