Inhibition of benzo[a]pyrene dihydrodiol epoxide mutagenicity by synthetic analogues of ellagic acid.
Dibenzo[b, d]pyran-6-one, hydroxylated and methoxylated derivatives of this ring system, and some other analogues of the natural product ellagic acid have been synthesized and examined as inhibitors of benzo[a]pyrene dihydrodiol epoxide (BPDE) mutagenicity in Salmonella typhimurium strain TA100. Some of these new compounds have inhibitory effectiveness comparable to the natural product. On the basis of our results, we suggest qualitative rules for predicting inhibitory activity of ellagic acid analogues.
Josephy
P D
PD
Department of Chemistry and Biochemistry, University of Guelph, Ont., Canada.
Lord
H L
HL
Snieckus
V A
VA
D015123:7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide / Q000633:toxicity*; D001580:Benzopyrenes / Q000494:pharmacology*; D004610:Ellagic Acid / Q000031:analogs & derivatives / Q000494:pharmacology*; D004852:Epoxy Compounds / Q000494:pharmacology; D009152:Mutagenicity Tests; D009154:Mutation; D012486:Salmonella typhimurium / Q000187:drug effects
D001580:Benzopyrenes; D004852:Epoxy Compounds; D004610:Ellagic Acid; D015123:7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide