Chemical structure and mutagenic activity of aminoimidazoquinolines and aminonaphthimidazoles related to 2-amino-3-methylimidazo[4,5-f]quinoline.
We have synthesized 11 heterocyclic aromatic amines with chemical structures related to that of 2-amino-3-methylimidazo [4,5-f] quinoline (IQ), a potent mutagen occurring in broiled sardines, fried beef and beef extract. The mutagenic activity of these IQ analogs was studied and compared with that of IQ using the Ames test with strain TA98 of Salmonella typhimurium in presence of a metabolic activation system (S9 mix) derived from rat liver. The mutagenic activities of the IQ analogs vary over a million-fold; structure-activity comparisons indicate major contributions of the methyl substitution in the imidazole ring and of the quinoline-N, and significant contributions of methylation of the exocyclic amino group and of the geometry of the entire ring system.
D000818:Animals; D001711:Biotransformation; D007093:Imidazoles / Q000138:chemical synthesis / Q000633:toxicity*; D066298:In Vitro Techniques; D009152:Mutagenicity Tests; D009153:Mutagens; D011804:Quinolines / Q000138:chemical synthesis / Q000633:toxicity*; D051381:Rats; D012486:Salmonella typhimurium / Q000235:genetics; D013329:Structure-Activity Relationship
D007093:Imidazoles; D009153:Mutagens; D011804:Quinolines