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Literature DB >> 271953

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

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

Abstract

Covalent binding of the benzo[a]pyrene metabolite (+/-)7beta,8alpha-dihydroxy-9alpha,10alpha-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.

Entities: Chemical Species

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Year: 1977 PMID： 271953 PMCID： PMC431688 DOI： 10.1073/pnas.74.12.5285

Source DB: PubMed Journal: Proc Natl Acad Sci U S A ISSN： 0027-8424 Impact factor: 11.205

23 in total

1. EVIDENCE FOR THE BINDING OF POLYNUCLEAR AROMATIC HYDROCARBONS TO THE NUCLEIC ACIDS OF MOUSE SKIN: RELATION BETWEEN CARCINOGENIC POWER OF HYDROCARBONS AND THEIR BINDING TO DEOXYRIBONUCLEIC ACID.

Authors: P BROOKES; P D LAWLEY
Journal: Nature Date: 1964-05-23 Impact factor: 49.962

2. A RAPID PERMETHYLATION OF GLYCOLIPID, AND POLYSACCHARIDE CATALYZED BY METHYLSULFINYL CARBANION IN DIMETHYL SULFOXIDE.

Authors: S HAKOMORI
Journal: J Biochem Date: 1964-02 Impact factor: 3.387

3. Benzo[a]pyrene diol epoxides: mechanism of enzymatic formation and optically active intermediates.

Authors: S K Yang; D W McCourt; J C Leutz; H V Gelboin
Journal: Science Date: 1977-06-10 Impact factor: 47.728

4. DNA strand scission by benzo[a]pyrene diol epoxides.

Authors: H B Gamper; A S Tung; K Straub; J C Bartholomew; M Calvin
Journal: Science Date: 1977-08-12 Impact factor: 47.728

5. Benzo[alpha]pyrene diol epoxide covalently binds to deoxyguanosine and deoxyadenosine in DNA.

Authors: T Meehan; K Straub; M Calvin
Journal: Nature Date: 1977-10-20 Impact factor: 49.962

6. Structural identification of the major DNA adduct formed by aflatoxin B1 in vitro.

Authors: J M Essigmann; R G Croy; A M Nadzan; W F Busby; V N Reinhold; G Büchi; G N Wogan
Journal: Proc Natl Acad Sci U S A Date: 1977-05 Impact factor: 11.205

7. Absolute configuration of a ribonucleic acid adduct formed in vivo by metabolism of benzo[a]pyrene.

Authors: K Nakanishi; H Kasai; H Cho; R G Harvey; A M Jeffrey; K W Jennette; I Weinstein
Journal: J Am Chem Soc Date: 1977-01-05 Impact factor: 15.419

8. Synthesis and reactions of the highly mutagenic 7,8-diol 9,10-epoxides of the carcinogen benzo[a]pyrene.

Authors: H Yagi; D R Thakker; O Hernandez; M Koreeda; D M Jerina
Journal: J Am Chem Soc Date: 1977-03-02 Impact factor: 15.419

9. Absolute sterochemistry of the highly mutagenic 7,8-diol 9,10-epoxides derived from the potent carcinogen trans-7,8-dihydroxy-7,8-dihydrobenzol[a]pyrene.

Authors: H Yagi; H Akagi; D R Thakker; H D Mah; M Koreeda; D M Jerina
Journal: J Am Chem Soc Date: 1977-03-30 Impact factor: 15.419

10. Identification of the persistently bound form of the carcinogen N-acetyl-2-aminofluorene to rat liver DNA in vivo.

Authors: J G Westra; E Kriek; H Hittenhausen
Journal: Chem Biol Interact Date: 1976-10-02 Impact factor: 5.192

28 in total

1. Mismatch repair processing of carcinogen-DNA adducts triggers apoptosis.

Authors: J Wu; L Gu; H Wang; N E Geacintov; G M Li
Journal: Mol Cell Biol Date: 1999-12 Impact factor: 4.272

Review 2. Nucleic acid adducts of chemical carcinogens and mutagens.

Authors: K Hemminki
Journal: Arch Toxicol Date: 1983-04 Impact factor: 5.153

3. Robust incision of Benoz[a]pyrene-7,8-dihyrodiol-9,10-epoxide-DNA adducts by a recombinant thermoresistant interspecies combination UvrABC endonuclease system.

Authors: Guo Hui Jiang; Milan Skorvaga; Deborah L Croteau; Bennett Van Houten; J Christopher States
Journal: Biochemistry Date: 2006-06-27 Impact factor: 3.162

4. Hydrolysis of benzo[a]pyrene diol epoxide and its covalent binding to DNA proceed through similar rate-determining steps.

Authors: T Meehan; D M Bond
Journal: Proc Natl Acad Sci U S A Date: 1984-05 Impact factor: 11.205

5. Low energy tandem mass spectrometry of deoxynucleoside adducts of polycyclic aromatic hydrocarbon dihydrodiol-epoxides.

Authors: P S Branco; M P Chiarelli; J O Lay; F A Beland
Journal: J Am Soc Mass Spectrom Date: 1995-04 Impact factor: 3.109

6. Covalent binding of BP-metabolites to DNA of cultured human hair follicle keratinocytes.

Authors: M W Hukkelhoven; A M Bronkhorst; A J Vermorken
Journal: Arch Toxicol Date: 1985-04 Impact factor: 5.153

7. Chloride ions catalyze the formation of cis adducts in the binding of anti-benzo[a]pyrene diol epoxide to nucleic acids.

Authors: A R Wolfe; J Yamamoto; T Meehan
Journal: Proc Natl Acad Sci U S A Date: 1994-02-15 Impact factor: 11.205

8. Induction of cytochrome CYPIA1 and formation of toxic metabolites of benzo[a]pyrene by rat aorta: a possible role in atherogenesis.

Authors: M J Thirman; J H Albrecht; M A Krueger; R R Erickson; D L Cherwitz; S S Park; H V Gelboin; J L Holtzman
Journal: Proc Natl Acad Sci U S A Date: 1994-06-07 Impact factor: 11.205

9. Interaction of DNA methyltransferase with aminofluorene and N-acetylaminofluorene modified poly(dC-dG).

Authors: M Ruchirawat; F F Becker; J N Lapeyre
Journal: Nucleic Acids Res Date: 1984-04-11 Impact factor: 16.971

10. Selective alkylation of carcinogenic 9-anthryloxirane at the N-3 position of adenine in DNA.

Authors: N C Yang; C W Chang
Journal: Proc Natl Acad Sci U S A Date: 1985-08 Impact factor: 11.205