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Kinetics of hydrolysis to tetraols and binding of benzo(a)pyrene-7,8-dihydrodiol-9,10-oxide and its tetraol derivatives to DNA. Conformation of adducts

Journal Article · · Biochem. Biophys. Res. Commun.; (United States)
 [1]; ; ; ;
  1. New York Univ., NY
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When the major reactive metabolite of benzo(a)pyrene, trans-7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene (anti-BPDE) is incubated with DNA in aqueous solution at 25/sup 0/C, both covalent binding and hydrolysis of anti-BPDE to its tetraols occur. Using fluorescence and absorption spectroscopy it is shown that hydrolysis of anti-BPDE is markedly accelerated by DNA. In the presence of 5A/sub 260/ units of DNA per ml in cacodylate buffer solution, at an initial concentration of DNA phosphate/anti-BPDE ratio of 100, both the extent of covalent binding to DNA (<7% of the total anti-BPDE initially present) and hydrolysis of anti-BPDE reach their maximum levels within less than five minutes after mixing. Absorption and electric linear dichroism spectra indicate that the tetraols bind non-covalently to DNA by an intercalation mechanism, whereas the covalent product displays the characteristics of an externally bound complex.

DOE Contract Number:
AS02-78EV04959; AS02-76EV02386
OSTI ID:
6459648
Journal Information:
Biochem. Biophys. Res. Commun.; (United States), Journal Name: Biochem. Biophys. Res. Commun.; (United States) Vol. 92:4; ISSN BBRCA
Country of Publication:
United States
Language:
English

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Related Subjects

550200 -- Biochemistry
560301* -- Chemicals Metabolism &amp; Toxicology-- Cells-- (-1987)
59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ABSORPTION SPECTROSCOPY
AROMATICS
BENZOPYRENE
BINDING ENERGY
BIOCHEMICAL REACTION KINETICS
BIOCHEMISTRY
BIOLOGICAL EFFECTS
CHEMISTRY
CLATHRATES
CONDENSED AROMATICS
COVALENCE
DNA
ENERGY
FLUORESCENCE
HYDROCARBONS
KINETICS
LUMINESCENCE
METABOLITES
NUCLEIC ACIDS
ORGANIC COMPOUNDS
REACTION KINETICS
SPECTROSCOPY