Literature DB >> 316186

Benzo(a)pyrene-7,8-dihydrodiol 9,10-oxide adenosine and deoxyadenosine adducts: structure and stereochemistry.

A M Jeffrey, K Grzeskowiak, I B Weinstein, K Nakanishi, P Roller, R G Harvey.   

Abstract

The structure and absolute stereoconfigurations of four adenosine adducts with (+/-)-7 alpha,8 beta-dihydroxy-9 beta, 10 beta-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene (BPDE) and their deoxyadenosine analogs have been determined. They result from both cis and trans addition of the N6 amino group of ademine to the 10 position of both enantiomers of BDPE. This was determined from studies of the nuclear magnetic resonance spectra, mass spectra, and circular dichroism spectra, as well as from their pKa values and chemical reactivities.

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Year:  1979        PMID： 316186     DOI： 10.1126/science.316186

Source DB:  PubMed          Journal:  Science        ISSN： 0036-8075            Impact factor:   47.728


  13 in total

Review 1.  Metabolism and activation of chemical carcinogens.

Authors:  E K Weisburger
Journal:  Mol Cell Biochem       Date:  1980-09-15       Impact factor: 3.396

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

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

3.  Benzo[a]pyrene diol epoxide-DNA cis adduct formation through a trans chlorohydrin intermediate.

Authors:  T Meehan; A R Wolfe; G R Negrete; Q Song
Journal:  Proc Natl Acad Sci U S A       Date:  1997-03-04       Impact factor: 11.205

4.  Carcinogenic epoxides of benzo[a]pyrene and cyclopenta[cd]pyrene induce base substitutions via specific transversions.

Authors:  E Eisenstadt; A J Warren; J Porter; D Atkins; J H Miller
Journal:  Proc Natl Acad Sci U S A       Date:  1982-03       Impact factor: 11.205

5.  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

6.  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

7.  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

8.  Crystal and molecular structure of a benzo[a]pyrene 7,8-diol 9,10-epoxide N2-deoxyguanosine adduct: absolute configuration and conformation.

Authors:  Isabella L Karle; Haruhiko Yagi; Jane M Sayer; Donald M Jerina
Journal:  Proc Natl Acad Sci U S A       Date:  2004-02-02       Impact factor: 11.205

9.  Base insertion and deletion mutations induced in an Escherichia coli plasmid by benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide.

Authors:  H Mizusawa; C H Lee; T Kakefuda; K McKenney; H Shimatake; M Rosenberg
Journal:  Proc Natl Acad Sci U S A       Date:  1981-11       Impact factor: 11.205

10.  Splicing mutations in the CHO DHFR gene preferentially induced by (+/-)-3 alpha,4 beta-dihydroxy-1 alpha,2 alpha-epoxy-1,2,3,4- tetrahydrobenzo[c]phenanthrene.

Authors:  A M Carothers; G Urlaub; J Mucha; R G Harvey; L A Chasin; D Grunberger
Journal:  Proc Natl Acad Sci U S A       Date:  1990-07       Impact factor: 11.205
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