Mutagenicity to Salmonella of the mono methylamino and N-cyanoethyl analogues of 4-dimethylaminoazobenzene (DAB) and 6-dimethylaminophenylazobenzthiazole (6BT).
Replacement of one of the methyl groups of the carcinogens 4-dimethylaminoazobenzene (DAB) and 6-dimethylaminophenylazobenzthiazole (6BT) with a cyanoethyl (-CH2CH2CN) substituent dramatically increases their mutagenic potency to Salmonella (strain TA98). The corresponding monomethylamino derivatives (-NHCH3) are more mutagenic than the parent dimethylamino [-N(CH3)2] compounds, but substantially less mutagenic than the cyanoethyl derivatives. All of these mutagenic activities are liver-S-9-dependent. The very similar dose response curves observed for the two cyanoethyl compounds argues for the formation of a common electrophilic intermediate from each.
D000818:Animals; D052160:Benzothiazoles; D001711:Biotransformation; D008862:Microsomes, Liver / Q000378:metabolism; D009152:Mutagenicity Tests; D009154:Mutation / Q000187:drug effects*; D051381:Rats; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics; D012995:Solubility; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000494:pharmacology*; D004124:p-Dimethylaminoazobenzene / Q000031:analogs & derivatives* / Q000494:pharmacology
D052160:Benzothiazoles; D013844:Thiazoles; C012103:N,N-dimethyl-4-(6-benzothiazolylazo)aniline; D004124:p-Dimethylaminoazobenzene