The identification and characterization of a urinary mutagen resulting from cigarette smoke.
The urine of a cigarette smoker who excretes exceptionally mutagenic urine was analyzed for several factors affecting mutagenicity. S. typhimurium strain TA98 was always more sensitive to XAD-2 urine concentrates than TA100. With TA98, as high as 85 revertants per ml of urine were produced. It was observed that incubation with beta-glucuronidase was not required for expression of mutagenicity but that a complete S9 mix was needed to convert the material in the concentrate to the ultimate mutagenic species. TLC and HPLC separation of the XAD-2 urine concentrate resulted in the identification of trace amounts of the bladder carcinogen, 2-aminonaphthalene (beta-naphthylamine) and a considerable amount of a possible metabolite of 2-aminonaphthalene, 2-amino-7-naphthol. The identity of the compounds was confirmed by mass spectral analysis, and 2-amino-7-naphthol was shown to be a mutagen for TA100 and TA98 when activated by rat-liver S9.
D000818:Animals; D001711:Biotransformation; D005966:Glucuronidase / Q000378:metabolism; D006801:Humans; D066298:In Vitro Techniques; D008099:Liver / Q000378:metabolism; D009152:Mutagenicity Tests; D009153:Mutagens / Q000302:isolation & purification* / Q000378:metabolism; D009284:Naphthols / Q000652:urine*; D051381:Rats; D012907:Smoking; D014556:Urine / Q000032:analysis
D009153:Mutagens; D009284:Naphthols; C037312:2-amino-7-naphthol; D005966:Glucuronidase