The formation of dihydrodiols by the chemical or enzymic oxidation of benz[a] anthracene and 7,12-dimethylbenz[a] anthracene.

@article{Tierney1978TheFO,
  title={The formation of dihydrodiols by the chemical or enzymic oxidation of benz[a] anthracene and 7,12-dimethylbenz[a] anthracene.},
  author={Brian Tierney and Alan Hewer and Alan D. MacNicoll and P. Giovanni Gervasi and H. W. E. Rattle and Christopher T Walsh and Philip L. Grover and P. Sims},
  journal={Chemico-biological interactions},
  year={1978},
  volume={23 2},
  pages={
          243-57
        }
}
When benz[a] anthracene was oxidised in a reaction mixture containing ascorbic acid, ferrous sulphate and EDTA, the non-K-region dihydrodiols, trans-1,2-dihydro-1,2-dihydroxybenz[a] anthracene and trans-3,4-dihydro-3,4-dihydroxybenz[a] anthracene together with small amounts of the 8,9- and 10,11-dihydrodiols were formed. When oxidised in a similar system, 7,12-dimethylbenz[a] anthracene yielded the K-region dihydrodiol, trans-5,6-dihydro-5,6-dihydroxy-7,12-dimethylbenz[a] anthracene and the non… Expand
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Additional evidence for the involvement of the 3,4-diol 1,2-oxides in the metabolic activation of 7,12-dimethylbenz[a]anthracene in mouse skin.
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Since other nucleic acid-hydrocarbon adducts were also present that have not been identified as resulting from the reaction of the 3,4-diol 1,2-oxides with DNA, other mechanisms may also be involved in the metabolic activation of 7,12-dimethylbenz[a]anthracene in mouse skin. Expand
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References

SHOWING 1-10 OF 31 REFERENCES
The metabolism of benz[a]anthracene and dibenz[a,h]anthracene and their 5,6-epoxy-5,6-dihydro derivatives by rat-liver homogenates.
TLDR
Dibenz[a,h]anthracene was hydroxylated by rat-liver homogenates on the 3,4-,5,6- or 8,9-bond to yield phenols and dihydrodihydroxy compounds and there was no evidence for metabolic action at the 7- and 14-positions. Expand
The preparation of dihydrodiols from 7-methylbenz[a]-anthracene.
TLDR
The ultra-violet, spectral and nuclear magnetic resonance (NMR) characteristics of the dihydrodiols are reported and the data used to assign the proposed structures are used to explain the unusual preferred conformation which the 8,9-dihydrodiol adopts. Expand
Metabolic pathways of 7,12-dimethylbenz[a]anthracene in hepatic microsomes.
  • S. K. Yang, W. V. Dower
  • Chemistry, Medicine
  • Proceedings of the National Academy of Sciences of the United States of America
  • 1975
TLDR
The epoxide hydratase inhibitor 1,2-epoxy-3, 3,3,3-trichloropropane was found to eliminate all dihydrodiol formation and markedly inhibit the formation of several dimethylbenzanthracene metabolites. Expand
The formation of dihydrodiols by chemical or enzymic oxidation of 3-methylcholanthrene.
TLDR
The chemical oxidation of 3-methylcholanthrene in an ascorbic acid-ferrous sulphate-EDTA reaction mixture gave all five possible dihydrodiols, identified by comparison of their UV and chromatographic characteristics with those of authentic standards. Expand
Exceptional carcinogenic activity of benz[a]anthracene 3,4-dihydrodiol in the newborn mouse and the bay region theory.
Benz[a]anthracene and the five metabolically possible trans-dihydrodiols of benz[a]anthracene were tested for carcinogenicity in newborn Swiss-Webster mice. Four hundred, 800, and 1600 nmolesExpand
The metabolic activation of 7-methylbenz(a)anthracene in mouse skin: High tumour-initiating activity of the 3,4-dihydrodiol
Summary 7-Methylbenz(a)anthracene and four related dihydrodiol metabolites were tested for their abilities to initiate tumour formation on mouse skin. A single application (25 μg) of the hydrocarbonExpand
The metabolism of benz(a)anthracene and dibenz(a,h)anthracene and their related "K-region" epoxides, cis-dihydrodiols and phenols by hamster embryo cells.
TLDR
The nature of some of the metabolites present in the cell media from hamster embryo cells that had been grown in the presence of benz, dibenz and their related K-region epoxides, phenols and cis -dihydrodiols has been investigated. Expand
Mutagenicity and cytotoxicity of benz[alpha]anthracene diol epoxides and tetrahydro-epoxides: exceptional activity of the bay region 1,2-epoxides.
  • A. Wood, R. Chang, +5 authors A. Conney
  • Medicine, Chemistry
  • Proceedings of the National Academy of Sciences of the United States of America
  • 1977
TLDR
The exceptional mutagenic activity of the 1,2-epoxide derivatives of benz[a]anthracene is consistent with and supportive of the hypothesis that bay region epoxides on saturated, angular benzo-rings of unsubstituted polycyclic aromatic hydrocarbons are ultimate carcinogens. Expand
High microsome-mediated mutagenicity of the 3,4-dihydrodiol of 7-methylbenz[a]anthracene in S. typhimurium TA 98.
TLDR
1,1-Trichloropropene 2,3-oxide, an inhibitor of epoxide hydratase, increased the microsome-mediated mutagenicity of 7-methylbenz[a]anthracene but did not alter that of the four related dihydrodiols. Expand
The effect of pretreatment with adrenal-protecting compounds on the metabolism of 7,12-dimethylbenz[a]anthracene and related compounds by rat-liver homogenates.
TLDR
Of a number of hydrocarbons and of derivatives of 3-methylcholanthrene tested as enzyme inducers, 3- methylcholanstrene itself was the most effective and appeared to involve increased metabolism of the methyl and hydroxymethyl groups. Expand
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