Benzo(a)pyrene bay-region sulfonates, a novel class of reactive intermediates
- Univ. of Kansas Medical Center, Kansas City (USA)
The mutagenicity of 7r,8t- dihydroxy- 9t,10t- epoxy-7,8,9,10- tetrahydrobenzo(a) pyrene (anti-BPDE) toward Salmonella typhimurium strain TA98 is enhanced by over 1.5-fold by the addition of 1-10 mM sulfite to the incubations. Sulfite itself is neither mutagenic nor toxic to the bacteria under these conditions. The major product of this reaction has been characterized by UV/visible and fluorescence spectroscopy, NI-FAB mass spectrometry, and proton NMR spectroscopy and is identified as 7,8,9-trihydroxy- 7,8,9,10- tetrahydrobenzo(a) pyrene-10-sulfonate (BPT-10-sulfonate). Further support for a key role of BPT-10-sulfonate in the enhancement of anti-BPDE mutagenicity is provided by our findings on the reactivity of this compound. These findings demonstrate that trapping of diol epoxides by sulfite, unlike the corresponding reactions of the epoxides with water or thiols, yields a new class of reactive intermediate which retains the ability to bind covalently to nucleic acids. Such reactive intermediates may play an important role in the sulfite-dependent enhancement of the genotoxicity of BP and BP derivatives.
- OSTI ID:
- 6411511
- Journal Information:
- Chemical Research in Toxicology; (USA), Journal Name: Chemical Research in Toxicology; (USA) Vol. 3:1; ISSN CRTOE; ISSN 0893-228X
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AROMATICS
CHALCOGENIDES
CONDENSED AROMATICS
EMISSION SPECTROSCOPY
FLUORESCENCE SPECTROSCOPY
HYDROCARBONS
MASS SPECTROSCOPY
MUTAGEN SCREENING
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
PYRENE
REACTION INTERMEDIATES
SCREENING
SPECTRA
SPECTROSCOPY
SULFONATES
SULFUR COMPOUNDS
SULFUR DIOXIDE
SULFUR OXIDES
ULTRAVIOLET SPECTRA
VISIBLE SPECTRA