The identification and characterization of a urinary mutagen resulting from cigarette smoke

Mutat Res. 1983 Apr;113(2):161-72. doi: 10.1016/0165-1161(83)90227-3.

Abstract

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.

Publication types

  • Comparative Study
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Biotransformation
  • Glucuronidase / metabolism
  • Humans
  • In Vitro Techniques
  • Liver / metabolism
  • Mutagenicity Tests
  • Mutagens / isolation & purification*
  • Mutagens / metabolism
  • Naphthols / urine*
  • Rats
  • Smoking*
  • Urine / analysis

Substances

  • Mutagens
  • Naphthols
  • 2-amino-7-naphthol
  • Glucuronidase