Genotoxicity of 2-halocinnamaldehydes in two bacterial assays. Induction of SOS repair and frame-shift mutation.
2-Chlorocinnamaldehyde and 2-bromocinnamaldehyde, compounds of practical interest, for example, as bacteriocides and fungicides or for utilization in light sensitive layers, were tested in the Ames preincubation test with various Salmonella typhimurium strains, and in the SOS chromotest with Escherichia coli PQ 37.2-Chlorocinnamaldehyde was clearly mutagenic in strain TA 100 (6081 revertants/mumol) and in strain TA 98 (3050 revertants/mumol) without S9 mix, and was clearly positive in the SOS chromotest (SOSIP = 0.181). 2-Bromocinnamaldehyde was a strong mutagen in strain TA 100 (105, 500 revertants/mumol), in strain TA98 (41567 revertants/mumol) and in strain TA 1538 (15825 revertants/mumol), and also unambiguously mutagenic in strain TA 1535 (2110 revertants/mumol) without S9 mix. The SOSIP in the SOS chromotest was 1.5. Addition of S9 mix led to a marked decrease in the mutagenic activity of 2-bromocinnamaldehyde in all strains tested. In the case of strain TA 1535, mutagenic activity was abolished or not significant in the presence of S9 mix. The possible primary mechanisms underlying these mutagenic effects are discussed. Frame-shift activity of these halocinnamaldehydes can be explained by their planar structure.
Eder
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E
Institute of Toxicology, University of Würzburg, Germany.
Deininger
C
C
Deininger
D
D
Weinfurtner
E
E
D000171:Acrolein / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D000818:Animals; D004926:Escherichia coli / Q000187:drug effects / Q000235:genetics; D016368:Frameshift Mutation; D066298:In Vitro Techniques; D008099:Liver / Q000378:metabolism; D009152:Mutagenicity Tests / Q000379:methods; D009153:Mutagens / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D051381:Rats; D017208:Rats, Wistar; D013014:SOS Response, Genetics / Q000187:drug effects*; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics; D013329:Structure-Activity Relationship
D009153:Mutagens; D000171:Acrolein; C012843:cinnamaldehyde