Literature DB >> 2519824

DNA adducts from carcinogenic and noncarcinogenic enantiomers of benzo[a]pyrene dihydrodiol epoxide.

S C Cheng1, B D Hilton, J M Roman, A Dipple.   

Abstract

The characterization of eight benzo[a]pyrene-deoxyribonucleoside adducts derived from reaction of the anti-dihydrodiol epoxide and deoxyguanylic and deoxyadenylic acids is described. It is reported that the epoxide ring is opened by the purine amino groups to yield similar amounts of both cis and trans products. NMR data show that the 7- and 8-hydroxyl groups are pseudodiaxial in the cis products and pseudodiequatorial in the trans products, and we suggest that these products arise from reaction with the diaxial and diequatorial conformers of the dihydrodiol epoxides, respectively. The chiral nature of the interactions of these metabolites with DNA restricts the range of products formed with this macromolecule, and a trans product with deoxyguanosine is the major product formed with either enantiomer of the anti-dihydrodiol epoxide.

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Year:  1989        PMID： 2519824     DOI： 10.1021/tx00011a011

Source DB:  PubMed          Journal:  Chem Res Toxicol        ISSN： 0893-228X            Impact factor:   3.739


  63 in total

1.  Benzo[a]pyrene diol epoxide adducts in DNA are potent suppressors of a normal topoisomerase I cleavage site and powerful inducers of other topoisomerase I cleavages.

Authors:  Y Pommier; G Kohlhagen; P Pourquier; J M Sayer; H Kroth; D M Jerina
Journal:  Proc Natl Acad Sci U S A       Date:  2000-02-29       Impact factor: 11.205

2.  Position-specific trapping of topoisomerase I-DNA cleavage complexes by intercalated benzo[a]- pyrene diol epoxide adducts at the 6-amino group of adenine.

Authors:  Y Pommier; G S Laco; G Kohlhagen; J M Sayer; H Kroth; D M Jerina
Journal:  Proc Natl Acad Sci U S A       Date:  2000-09-26       Impact factor: 11.205

3.  Translesion replication of benzo[a]pyrene and benzo[c]phenanthrene diol epoxide adducts of deoxyadenosine and deoxyguanosine by human DNA polymerase iota.

Authors:  Ekaterina G Frank; Jane M Sayer; Heiko Kroth; Eiji Ohashi; Haruo Ohmori; Donald M Jerina; Roger Woodgate
Journal:  Nucleic Acids Res       Date:  2002-12-01       Impact factor: 16.971

4.  Error-prone lesion bypass by human DNA polymerase eta.

Authors:  Y Zhang; F Yuan; X Wu; O Rechkoblit; J S Taylor; N E Geacintov; Z Wang
Journal:  Nucleic Acids Res       Date:  2000-12-01       Impact factor: 16.971

5.  Dnmt3a-CD is less susceptible to bulky benzo[a]pyrene diol epoxide-derived DNA lesions than prokaryotic DNA methyltransferases.

Authors:  Olga V Lukashevich; Vladimir B Baskunov; Maria V Darii; Alexander Kolbanovskiy; Alexander A Baykov; Elizaveta S Gromova
Journal:  Biochemistry       Date:  2011-01-13       Impact factor: 3.162

6.  Mutagenic Replication of N2-Deoxyguanosine Benzo[a]pyrene Adducts by Escherichia coli DNA Polymerase I and Sulfolobus solfataricus DNA Polymerase IV.

Authors:  A S Prakasha Gowda; Jacek Krzeminski; Shantu Amin; Zucai Suo; Thomas E Spratt
Journal:  Chem Res Toxicol       Date:  2017-04-19       Impact factor: 3.739

7.  Stereochemistry-dependent bending in oligonucleotide duplexes induced by site-specific covalent benzo[a]pyrene diol epoxide-guanine lesions.

Authors:  R Xu; B Mao; J Xu; B Li; S Birke; C E Swenberg; N E Geacintov
Journal:  Nucleic Acids Res       Date:  1995-06-25       Impact factor: 16.971

8.  ATP-dependent transport of glutathione conjugate of 7beta, 8alpha-dihydroxy-9alpha,10alpha-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene in murine hepatic canalicular plasma membrane vesicles.

Authors:  S K Srivastava; X Hu; H Xia; R J Bleicher; H A Zaren; J L Orchard; S Awasthi; S V Singh
Journal:  Biochem J       Date:  1998-06-15       Impact factor: 3.857

9.  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

10.  Versatility of Y-family Sulfolobus solfataricus DNA polymerase Dpo4 in translesion synthesis past bulky N2-alkylguanine adducts.

Authors:  Huidong Zhang; Robert L Eoff; Ivan D Kozekov; Carmelo J Rizzo; Martin Egli; F Peter Guengerich
Journal:  J Biol Chem       Date:  2008-12-04       Impact factor: 5.157
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