Transformation of arylamines into direct-acting mutagens by reaction with nitrite
Kato, T.; Tadokoro, N.; Tsutsui, M.; Kikugawa, K.
Mutation Research 249(1): 243-254
1991
ISSN/ISBN: 0027-5107 PMID: 2067537 Document Number: 368401
Arylamines including aniline (I), 1-naphthylamine (II), 2-napthylamine (III), 2-aminofluorene (IV), 1-aminoanthracene (v) and 1-aminopyrene (VI) were treated with 4 equivalent amounts of nitrite at pH 3 and 37.degree. 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 strains were 110/0.05 .mu. mole I, 970/0.055 .mu. mole IV, 620/0.10 .mu. mole V and 870/0.02 .mu.mole 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 unstabel fluorene-2-diazonium salt (IV1). The mutagens from V were N3O3-introduced anthraceme (V1-1) and 1-nitroanthracene (V2), and those from VI were unidentified nitro-introduced compound (VI1) and 1-nitropyrene (VI2).