Structural determination of a directly mutagenic amino-nitrobiphenyl as the S9 metabolite of 2,4,2',4'-tetranitrobiphenyl in Salmonella typhimurium TA98.
In order to elucidate the mechanisms of mutagenic activation of nitrobiphenyls by mammalian activation systems, 2,4,2',4'-tetranitrobiphenyl was incubated with S9 and its mutagenic metabolites were separated by SiO2 and Al2O3 column chromatography. The most mutagenic diamino-dinitrobiphenyl was isolated from the reaction mixture of 2,4,2',4'-tetranitrobiphenyl with S9 mix at 37 degrees C for 48 h, and its mutability was 4646 revertants/50 ng in Salmonella typhimurium TA98 without S9 mix. The deamination product of this most mutagenic metabolite was identical to 2,4'-dinitrobiphenyl by gas chromatography-mass spectrometry. Therefore, the structure of the metabolite was determined as 2,4'-diamino-2',4-dinitrobiphenyl by its chemical and physico-chemical properties.
Hirayama
T
T
Department of Food Chemistry and Environmental Toxicology, Kyoto Pharmaceutical University, Japan.
Iguchi
K
K
Yoshida
S
S
Yamanaka
Y
Y
Watanabe
T
T
D000818:Animals; D001713:Biphenyl Compounds / Q000378:metabolism / Q000633:toxicity*; D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D066298:In Vitro Techniques; D008110:Liver Extracts / Q000378:metabolism*; D008297:Male; D013058:Mass Spectrometry; D009152:Mutagenicity Tests; D011721:Pyrenes / Q000633:toxicity; D051381:Rats; D011919:Rats, Inbred Strains; D012486:Salmonella typhimurium / Q000235:genetics*
D001713:Biphenyl Compounds; D008110:Liver Extracts; D011721:Pyrenes; C067778:2,4'-diamino-2',4-dinitrobiphenyl; C067775:2,4,2',4'-tetranitrobiphenyl; C032668:1-nitropyrene