Literature DB >> 1066679

(+/-)-7alpha,8beta-dihydroxy-9beta,10beta-epoxy-7,8,9,10-tetrahydrobenzo(a)-pyrene is an intermediate in the metabolism and binding to DNA of benzo(a)pyrene.

H W King, M R Osborne, F A Beland, R G Harvey, P Brookes.   

Abstract

The addition of borate buffer to the aqueous methanol used to elute hydrocarbon-deoxyribonucleoside derivatives from an LH 20 Sephadex column resulted in the separation of the products of reaction with DNA of the stereoisomers, (+/-)7alpha,8beta-dihydroxy-9alpha,10alpha-epoxy- and (+/-)-7alpha,8beta-dihydroxy-9beta,10beta-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrenes, i.e., the syn- and anti-benzo(a)pyrene-diolepoxide, respecitvely. By this technique it was shown that the microsome-mediated binding to DNA of benzo(a)pyrene-7,8-dihydrodiol involved exclusively the anti-benzo(a)pyrene-diolepoxide. The benzo(a)pyrene binding to DNA that resulted on exposure of BHK21/C13 cells to this carcinogen was also shown to result predominantly by reaction of the anti-benzo(a)pyrene-diolepoxide. However, in this case other derivatives, including the syn-benzo(a)pyrene diolepoxide, might also be involved.

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Year:  1976        PMID： 1066679      PMCID： PMC430711          DOI： 10.1073/pnas.73.8.2679

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


  12 in total

1.  Carbonium ion as ultimate carcinogen of polycyclic aromatic hydrocarbons.

Authors:  P B Hulbert
Journal:  Nature       Date:  1975-07-10       Impact factor: 49.962

2.  Letter: Synthesis of (+/-)-7 beta,8alpha-dihydroxy-9 beta,10beta-epoxy-7,8,-9,10-tetrahydrobenzo(a)pyrene, a potential metabolite of the carcinogen benzo(a)pyrene with stereochemistry related to the antileukemic triptolides.

Authors:  H Yagi; O Hernandez; D M Jerina
Journal:  J Am Chem Soc       Date:  1975-11-12       Impact factor: 15.419

3.  The reaction of 7,8-dihydro-7,8-dihydroxybenzo (a) pyrene-9,10-oxide with DNA in relation to the benzo (a) pyrene-DNA products isolated from cells.

Authors:  M R Osborne; M H Thompson; E M Tarmy; F A Beland; R G Harvey; P Brookes
Journal:  Chem Biol Interact       Date:  1976-06       Impact factor: 5.192

4.  Exceptional mutagenicity of a benzo(a)pyrene diol epoxide in cultured mammalian cells.

Authors:  R F Newbold; P Brookes
Journal:  Nature       Date:  1976-05-06       Impact factor: 49.962

5.  On the nature of the product which results when 7,8-dihydro-7,8-dihydroxybenzo(a)pyrene is metabolised in vitro and bound to DNA.

Authors:  H W King; M H Thompson; E M Tarmy; P Brookes; R G Harvey
Journal:  Chem Biol Interact       Date:  1976-06       Impact factor: 5.192

6.  Metabolic activation of benzo(a)pyrene proceeds by a diol-epoxide.

Authors:  P Sims; P L Grover; A Swaisland; K Pal; A Hewer
Journal:  Nature       Date:  1974-11-22       Impact factor: 49.962

7.  Metabolic conversion of benzo(a)pyrene by Syrian hamster liver microsomes and binding of metabolites to deoxyribonucleic acid.

Authors:  A Borgen; H Darvey; N Castagnoli; T T Crocker; R E Rasmussen; I Y Wang
Journal:  J Med Chem       Date:  1973-05       Impact factor: 7.446

8.  Rat liver microsome-mediated binding of benzo(a)pyrene metabolites to DNA.

Authors:  M H Thompson; H W King; M R Osborne; P Brookes
Journal:  Int J Cancer       Date:  1976-02-15       Impact factor: 7.396

9.  Identification of mutagenic metabolites of benzo(a)pyrene in mammalian cells.

Authors:  E Huberman; L Sachs; S K Yang; V Gelboin
Journal:  Proc Natl Acad Sci U S A       Date:  1976-02       Impact factor: 11.205

10.  Isolation of the hydrocarbon-deoxyribonucleoside products from the DNA of mouse embryo cells treated in culture with 7-methylbenz(a)anthracene-3H.

Authors:  W M Baird; P Brookes
Journal:  Cancer Res       Date:  1973-10       Impact factor: 12.701
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  18 in total

1.  Excision repair of benzo[a]pyrene-deoxyguanosine adducts in baby hamster kidney 21/C13 cells and in secondary mouse embryo fibroblasts C57BL/6J.

Authors:  K Shinohara; P A Cerutti
Journal:  Proc Natl Acad Sci U S A       Date:  1977-03       Impact factor: 11.205

2.  A bacteriophage system for screening and study of biologically active polycyclic aromatic hydrocarbons and related compounds.

Authors:  W T Hsu; R G Harvey; E J Lin; S B Weiss
Journal:  Proc Natl Acad Sci U S A       Date:  1977-04       Impact factor: 11.205

3.  Tumorigenicity of the optical enantiomers of the diastereomeric benzo[a]pyrene 7,8-diol-9,10-epoxides in newborn mice: exceptional activity of (+)-7beta,8alpha-dihydroxy-9alpha,10alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene.

Authors:  M K Buening; P G Wislocki; W Levin; H Yagi; D R Thakker; H Akagi; M Koreeda; D M Jerina; A H Conney
Journal:  Proc Natl Acad Sci U S A       Date:  1978-11       Impact factor: 11.205

4.  Effect of benzo[a]pyrene-diolepoxide on infectivity and in vitro translation of phage MS2 RNA.

Authors:  D Sagher; R G Harvey; W T Hsu; S B Weiss
Journal:  Proc Natl Acad Sci U S A       Date:  1979-02       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.  Metabolic activations of polycyclic hydrocarbons. Structure-activity relationships.

Authors:  R E Lehr; D M Jerina
Journal:  Arch Toxicol       Date:  1977-12-30       Impact factor: 5.153

7.  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

8.  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

9.  Effect of histone acetylation on the formation and removal of B(a)P chromatin adducts.

Authors:  A Kootstra
Journal:  Nucleic Acids Res       Date:  1982-05-11       Impact factor: 16.971

10.  Binding of pyrene to DNA, base sequence specificity and its implication.

Authors:  F M Chen
Journal:  Nucleic Acids Res       Date:  1983-10-25       Impact factor: 16.971
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