Mutagenicity of some synthetic quinolines and quinoxalines related to IQ, MeIQ or MeIQx in Ames test.
3-Methyl- and 3,4-dimethyl-3H-imidazo[4,5-f]quinoline, 3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline, N6-methyl- and N6,7-dimethylquinoline-5,6-diamine, as well as N6,3-dimethylquinoxaline-5,6-diamine, have been synthesized. Only the first-mentioned compound was active in Ames test; the response was equal for Salmonella typhimurium TA98 and TA100, regardless of enzymatic activation (S9). However, its mutagenicity to TA98 + S9 was 300-1300 times smaller than the values reported for the related compounds, 3-methyl- and 3,4-dimethyl-3H-imidazo[4,5-f]quinolin-2-amine ('IQ' and 'MeIQ'), and for 3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-amine ('MeIQx'). Hence, the presence of the imidazole ring and the 2-amino group in the molecule seems to be important for the high mutagenicity of the latter compounds.
D000818:Animals; D001711:Biotransformation; D008862:Microsomes, Liver / Q000378:metabolism; D009152:Mutagenicity Tests; D009153:Mutagens; D009154:Mutation; D011804:Quinolines / Q000138:chemical synthesis / Q000633:toxicity*; D011810:Quinoxalines / Q000138:chemical synthesis / Q000633:toxicity*; D051381:Rats; D012486:Salmonella typhimurium / Q000187:drug effects; D013045:Species Specificity; D013329:Structure-Activity Relationship
D009153:Mutagens; D011804:Quinolines; D011810:Quinoxalines