Literature DB >> 5584001

The metabolism of 7- and 12-methylbenz[a]anthracene and their derivatives.

P Sims.   

Abstract

1. 7- and 12-Methylbenz[a]anthracene were converted by rat-liver homogenates into the corresponding hydroxymethyl derivatives, products that are probably the 8,9-dihydro-8,9-dihydroxy and the 5,6-dihydro-5,6-dihydroxy derivatives, and a number of phenolic products. 2. Both hydrocarbons were converted into glutathione conjugates; that from 7-methylbenz[a]anthracene was also formed, together with 5,6-dihydro-5,6-dihydroxy- and 5-hydroxy-benz[a]anthracene, from 5,6-epoxy-5,6-dihydro-7-methylbenz[a]anthracene. 3. 7- and 12-Hydroxymethyl-benz[a]anthracene were converted into products that are probably 8,9-dihydro-8,9-dihydroxy derivatives, and into phenols. 4. The preparation of a number of derivatives of the hydrocarbons is described. 5. The oxidation of the hydrocarbons with lead tetra-acetate was investigated.

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Year:  1967        PMID: 5584001      PMCID: PMC1198349          DOI: 10.1042/bj1050591

Source DB:  PubMed          Journal:  Biochem J        ISSN: 0264-6021            Impact factor:   3.857


  9 in total

1.  Metabolism of polycyclic compounds. 24. The metabolism of benz[alpha]anthracene.

Authors:  E Boyland; P Sims
Journal:  Biochem J       Date:  1964-06       Impact factor: 3.857

2.  Metabolism of polycyclic compounds. 23. The metabolism of pyrene in rats and rabbits.

Authors:  E Boyland; P Sims
Journal:  Biochem J       Date:  1964-02       Impact factor: 3.857

3.  Induction of adrenal damage and cancer with metabolites of 7,12-dimethylbenz(a)anthracene.

Authors:  E Boyland; P Sims; C Huggins
Journal:  Nature       Date:  1965-08-21       Impact factor: 49.962

4.  The metabolism of benzo[a]pyrene by rat-liver homogenates.

Authors:  P Sims
Journal:  Biochem Pharmacol       Date:  1967-04       Impact factor: 5.858

5.  The metabolism of benz[a]anthracene and dibenz[a,h]anthracene and their 5,6-epoxy-5,6-dihydro derivatives by rat-liver homogenates.

Authors:  E Boyland; P Sims
Journal:  Biochem J       Date:  1965-10       Impact factor: 3.857

6.  The metabolism of 3-methylcholanthrene and some related compounds by rat-liver homogenates.

Authors:  P Sims
Journal:  Biochem J       Date:  1966-01       Impact factor: 3.857

7.  The effect of pretreatment with adrenal-protecting compounds on the metabolism of 7,12-dimethylbenz[a]anthracene and related compounds by rat-liver homogenates.

Authors:  E Boyland; P Sims
Journal:  Biochem J       Date:  1967-08       Impact factor: 3.857

8.  METABOLISM OF POLYCYCLIC COMPOUNDS. THE METABOLISM OF 7,12-DIMETHYLBENZ(ALPHA)ANTHRACENE BY RAT-LIVER HOMOGENATES.

Authors:  E BOYLAND; P SIMS
Journal:  Biochem J       Date:  1965-06       Impact factor: 3.857

9.  Selective adrenal necrosis and apoplexy induced by 7, 12-dimethylbenz(a)anthracene.

Authors:  C HUGGINS; S MORII
Journal:  J Exp Med       Date:  1961-11-01       Impact factor: 14.307

  9 in total
  6 in total

1.  Molecular characteristics of some carcinogenic hydrocarbons.

Authors:  E Cavalieri; M Calvin
Journal:  Proc Natl Acad Sci U S A       Date:  1971-06       Impact factor: 11.205

2.  Aryl hydrocarbon hydroxylase and polycyclic hydrocarbon tumorigenesis: effect of the enzyme inhibitor 7,8-benzoflavone on tumorigenesis and macromolecule binding.

Authors:  N Kinoshita; H V Gelboin
Journal:  Proc Natl Acad Sci U S A       Date:  1972-04       Impact factor: 11.205

3.  Metabolic pathways of 7,12-dimethylbenz[a]anthracene in hepatic microsomes.

Authors:  S K Yang; W V Dower
Journal:  Proc Natl Acad Sci U S A       Date:  1975-07       Impact factor: 11.205

4.  Epoxy derivatives of aromatic polycyclic hydrocarbons. The preparation and metabolism of epoxides related to 7,12-dimethylbenz(a)anthracene.

Authors:  P Sims
Journal:  Biochem J       Date:  1973-02       Impact factor: 3.857

5.  Metabolism of 7-methylbenz[a]anthracene and 7-hydroxymethylbenz[a]anthracene by Cunninghamella elegans.

Authors:  C E Cerniglia; P P Fu; S K Yang
Journal:  Appl Environ Microbiol       Date:  1982-09       Impact factor: 4.792

6.  Biological activities of dihydrodiols derived from two polycyclic hydrocarbons in rodent test systems.

Authors:  I Chouroulinkov; A Gentil; B Tierney; P L Grover; P Sims
Journal:  Br J Cancer       Date:  1979-04       Impact factor: 7.640

  6 in total

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