Identification of the major adducts formed by reaction of benzo(a)pyrene diol epoxide with DNA in vitro

Journal Article · Wed Nov 30 19:00:00 EST 1977 · Proc. Natl. Acad. Sci. U.S.A.; (United States)

DOI:https://doi.org/10.1073/pnas.74.12.5285· OSTI ID:6756267

Straub, K M; Meehan, T; Burlingame, A L; Calvin, M

Covalent binding of the benzo(a)pyrene metabolite (+-)7..beta..,8..cap alpha..-dihydroxy-9..cap alpha..,10..cap alpha..-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene to calf thymus DNA was investigated. Enzymatic hydrolysis of the carcinogen-modified DNA and subsequent separation via reversed-phase high-pressure liquid chromatography resulted in the detection and isolation of seven distinct products. High-resolution mass spectrometry indicates that these products are covalent adducts of deoxyguanosine, deoxyadenosine, and deoxycytidine. The deoxyguanosine and deoxyadenosine adducts involve binding between the activated hydrocarbon (benzo(a)pyrene diol epoxide) and exocyclic amino groups of the respective purines.

• Research Organization: Univ. of California, Berkeley
• OSTI ID: 6756267
• Journal Information: Proc. Natl. Acad. Sci. U.S.A.; (United States), Journal Name: Proc. Natl. Acad. Sci. U.S.A.; (United States) Vol. 74:12; ISSN PNASA
• Country of Publication: United States
• Language: English

Related Subjects

550200* -- Biochemistry
560300 -- Chemicals Metabolism & Toxicology
59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ADENINES
AMINES
AROMATICS
AZINES
BENZOPYRENE
CARCINOGENS
CELL CONSTITUENTS
CHEMICAL ACTIVATION
CHEMICAL BONDS
CHEMICAL REACTIONS
CHROMATOGRAPHY
CONDENSED AROMATICS
CYTOSINE
DNA
EPOXIDES
GUANINE
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROXY COMPOUNDS
IN VITRO
LIQUID COLUMN CHROMATOGRAPHY
MASS SPECTROSCOPY
METABOLITES
MICROSOMES
NUCLEIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANOIDS
PURINES
PYRIMIDINES
SEPARATION PROCESSES
SPECTROSCOPY