Transformation of arylamines into direct-acting mutagens by reaction with nitrite.
Arylamines including aniline (I), 1-naphthylamine (II), 2-naphthylamine (III), 2-aminofluorene (IV), 1-aminoanthracene (V) and 1-aminopyrene (VI) were treated with 4 equivalent amounts of nitrite at pH3 and 37 degrees C for 4 h. The reaction mixtures of I, IV, V and VI showed mutagenicity to Salmonella typhimurium TA98 and TA100 strains without metabolic activation. The numbers of His+ revertant colonies to TA98 strain were 110/0.05 mumole I, 970/0.055 mumole IV, 620/0.10 mumole V and 870/0.02 mumole VI. These arylamines were converted into mutagens with diazoquinone, diazonium and nitro functions depending on their structures. The mutagen from I was p-diazoquinone (I2). The mutagen from IV was highly unstable fluorene-2-diazonium salt (IV1). The mutagens from V were N3O3-introduced anthracene (V1-1) and 1-nitroanthracene (V2), and those from VI were unidentified nitro-introduced compound (VI1) and 1-nitropyrene (VI2).
Kato
T
T
Tokyo College of Pharmacy, Japan.
Tadokoro
N
N
Tsutsui
M
M
Kikugawa
K
K
D015057:1-Naphthylamine / Q000737:chemistry / Q000493:pharmacokinetics / Q000633:toxicity; D015073:2-Acetylaminofluorene / Q000737:chemistry / Q000493:pharmacokinetics / Q000633:toxicity; D015081:2-Naphthylamine / Q000737:chemistry / Q000493:pharmacokinetics / Q000633:toxicity; D000588:Amines / Q000737:chemistry / Q000633:toxicity*; D000814:Aniline Compounds / Q000737:chemistry / Q000493:pharmacokinetics / Q000633:toxicity; D000873:Anthracenes / Q000737:chemistry / Q000493:pharmacokinetics / Q000633:toxicity; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D006863:Hydrogen-Ion Concentration; D009152:Mutagenicity Tests; D009153:Mutagens; D009573:Nitrites / Q000737:chemistry*; D011721:Pyrenes / Q000737:chemistry / Q000493:pharmacokinetics / Q000633:toxicity; D012486:Salmonella typhimurium / Q000235:genetics; D013056:Spectrophotometry, Ultraviolet
D000588:Amines; D000814:Aniline Compounds; D000873:Anthracenes; D009153:Mutagens; D009573:Nitrites; D011721:Pyrenes; C049062:1-aminoanthracene; D015057:1-Naphthylamine; D015073:2-Acetylaminofluorene; D015081:2-Naphthylamine; C004482:1-aminopyrene; C023650:aniline