The genotoxicity of 2-bromoacrolein and 2,3-dibromopropanal.
2-Bromoacrolein (2-BA) and 2,3-dibromopropanal (2,3-DBPA), an identified and a postulated reactive metabolite of tris(2,3-dibromopropyl)phosphate (Tris-BP), respectively, were found to cause mutations in Salmonella typhimurium TA 100 both in the absence and presence of a metabolic system. 2-BA, as well as 2,3-DBPA, caused extensive DNA single-stranded breaks as evidenced by alkaline elution of DNA from exposed Reuber hepatoma cells in culture. The data with Syrian hamster embryo cells suggest that both 2-BA and 2,3-DBPA were more potent than Tris-BP in transforming these cells in culture. On the other hand, neither 2-BA, nor 2,3-DBPA, was found to cause increased unscheduled DNA repair synthesis in isolated rat hepatocytes in monolayer cultures, whereas Tris-BP had a significant effect at low concentrations (10-50 microM). There was no correlation between the observed mutagenic effects of 2-BA and 2,3-DBPA and their alkylating activities using the nitrobenzyl-pyridine test. The genotoxic effects associated with 2-BA and its detection in microsomal incubations makes it a likely candidate for a role in the mutagenicity of Tris-BP.
D000171:Acrolein / Q000031:analogs & derivatives / Q000378:metabolism / Q000633:toxicity*; D000447:Aldehydes / Q000633:toxicity*; D000818:Animals; D002471:Cell Transformation, Neoplastic; D006224:Cricetinae; D004260:DNA Repair; D066298:In Vitro Techniques; D008099:Liver / Q000378:metabolism; D008297:Male; D008647:Mesocricetus; D009153:Mutagens; D051381:Rats; D011919:Rats, Inbred Strains
D000447:Aldehydes; D009153:Mutagens; C041548:2-bromoacrolein; C045818:2,3-dibromopropanal; D000171:Acrolein