Stereoselective metabolism of 6-bromobenzo[a]pyrene by rat liver microsomes: absolute configuration of trans-dihydrodiol metabolites.

@article{Fu1982StereoselectiveMO,
  title={Stereoselective metabolism of 6-bromobenzo[a]pyrene by rat liver microsomes: absolute configuration of trans-dihydrodiol metabolites.},
  author={Peter P. Fu and S. K. Yang},
  journal={Biochemical and biophysical research communications},
  year={1982},
  volume={109 3},
  pages={
          927-34
        }
}
  • P. Fu, S. K. Yang
  • Published 15 December 1982
  • Chemistry, Biology
  • Biochemical and biophysical research communications
Stereoselective metabolism of 7-nitrobenz(a)anthracene to 3,4- and 8,9- trans-dihydrodiols.
  • P. Fu, S. K. Yang
  • Chemistry, Biology
    Biochemical and biophysical research communications
  • 1983
Stereoselectivity of rat liver microsomal enzymes in the metabolism of 7-fluorobenz(a)anthracene and mutagenicity of metabolites.
TLDR
Proton nuclear magnetic resonance spectral analyses indicated that the fluoro substituent causes 7-FBA trans-5,6- and 8,9-dihydrodiols to adopt preferentially quasidiaxial conformations, which may be the major metabolites which contribute to the carcinogenic properties of 5-Fluorobenz(a)anthracene.
Stereoselective metabolism of 8- and 9-fluorobenzo[a]pyrene by rat liver microsomes: absolute configurations of trans-dihydrodiol metabolites.
  • M. Chou, P. Fu
  • Chemistry, Biology
    Journal of toxicology and environmental health
  • 1984
TLDR
Comparison of the circular dichroism spectra of BaP 4R,5R-dihydrodiol, 6-bromo-BaP 7R,8R-DihydRodiol, and 6-fluoro-Ba p 7R-8R -dihYDrodiol with those of the respective dihydrodiol metabolites allowed assignments of an R,R absolute configuration to the major enantiomers of the three dihydRodiol metabolites.
Microsomal metabolism of 4-(N,N-diacetylamino)benzo[a]pyrene: a potent mutagenic arylamide derived from a carcinogenic polycyclic aromatic hydrocarbon.
TLDR
It is indicated that the N,N-diacetylamino substitutent at the 4-carbon of benzo[a]pyrene inhibits metabolism at the peri position (3-carbon) and positions (6, 7-, and 8-carbons) remote from the substituent.
Direct enantiomeric resolution of some 7,12-dimethylbenz[a]anthracene derivatives by high-performance liquid chromatography with ionically and covalently bonded chiral stationary phases.
TLDR
The direct resolution of the enantiomers of the diol derivatives of trans-3,4-dihydrodiol, trans-5,6- dihyd Rodiol, and 8,9,10,11-tetrahydro-trans-8,9-diol of 7,12-dimethylbenz(a)anthracene was evaluated by high-performance liquid chromatography.
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References

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Binding of benzo[a]pyrene 7,8-diol-9,10-epoxides to DNA, RNA, and protein of mouse skin occurs with high stereoselectivity.
TLDR
Polymer adducts from diastereomeric diol epoxides were formed stereospecifically from their corresponding 7,8-dihydrodiols, and binding occurs preferentially at the 2-amino group of guanine in cellular RNA and DNA in vivo.
Synthesis of high specific activity benzo[a]pyrene-6-t and its K-region oxidized derivatives
The potent carcinogen benzo[a]pyrene specifically tritiated in the 6-position was synthesized through hydrogenation of 6-bromobenzo[a]pyrene with tritium gas. The benzo[a]pyrene-6-t was then employed
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