Mutagenic activity of 6-aminoquinoxalines in Salmonella typhimurium.
Mutagenicity of 6-aminoquinoxaline derivatives was tested with Salmonella typhimurium strains TA98 and TA100 in the presence and absence of S9 mix from the viewpoint that the 6-aminoquinoxaline skeleton is a common unit of mutagenic imidazoquinoxalines. We tested nine compounds: 5-methyl-6-methylaminoquinoxaline (1), 3,5-dimethyl-6-methylaminoquinoxaline (2), 2,5-dimethyl-6-methylaminoquinoxaline (3), 6-methylamino-2,3,5-trimethylquinoxaline (4), 2,3-diethyl-5-methyl-6-methylaminoquinoxaline (5), 5-methyl-6-methylamino 3-phenylquinoxaline (6), 6-amino-2,3,5-trimethylquinoxaline (7), 6-dimethylamino-2,3,5- trimethylaminoquinoxaline (8), 6-amino-2,3-dimethylquinoxaline (9). These compounds showed the mutagenic activity for both TA98 and TA100 in the presence of S9 mix, where they were more sensitive for TA100 strain. Methyl groups at the 2, 3 and/or 5 positions increased the potency of mutagenicity (1 < 2 < 3 << 4, 9 < 7). However, ethyl groups at the 2 and 3 positions lowered the mutagenicity of the methyl substitute but elevated it of the parental compound (1 < 5 < 4). A methyl group at the N6 position decreased the mutagenicity (7 > 4 > 8).
Terao
Y
Y
Graduate School of Nutritional and Environmental Sciences, University of Shizuoka, Japan.
Achiwa
I
I
Kishino
S
S
Matsumura
Y
Y
Shiozawa
T
T
Matsushita
H
H
D000588:Amines / Q000138:chemical synthesis / Q000633:toxicity*; D004305:Dose-Response Relationship, Drug; D009152:Mutagenicity Tests; D009153:Mutagens / Q000138:chemical synthesis / Q000633:toxicity*; D011810:Quinoxalines / Q000138:chemical synthesis / Q000633:toxicity*; D012486:Salmonella typhimurium; D013329:Structure-Activity Relationship
D000588:Amines; D009153:Mutagens; D011810:Quinoxalines