Epoxy derivatives of aromatic polycyclic hydrocarbons. The preparation of benz( )anthracene 8,9-oxide and 10,11-dihydrobenz( )anthracene 8,9-oxide and their metabolism by rat liver preparations.

The Biochemical journal ·Vol. 125 ·No. 1 ·1971-11-00 ·Pages 159-68

Sims P

Abstract

The syntheses of 10,11-dihydrobenz[a]anthracene 8,9-oxide, benz[a]anthracene 8,9-oxide and 9-hydroxybenz[a]anthracene are described, together with those of a number of related compounds. The epoxides react both chemically and enzymically with water to yield the corresponding dihydrodiols and with reduced glutathione to form glutathione conjugates, and they react chemically with N-acetylcysteine to yield the corresponding mercapturic acids. 8,9-Dihydro-8,9-dihydroxybenz[a]anthracene, formed enzymically from benz[a]anthracene 8,9-oxide, was identical with a dihydrodiol formed when benz[a]anthracene was metabolized by rat liver homogenates. Similarly 10,11-dihydrobenz[a]anthracene 8,9-oxide yielded a dihydrodiol identical with the product formed when 10,11-dihydrobenz[a]anthracene was metabolized.

MeSH Terms

Animals Benz(a)Anthracenes/chemical synthesis,metabolism Chromatography, Paper Chromatography, Thin Layer Ethers, Cyclic/chemical synthesis,metabolism In Vitro Techniques Liver/metabolism Male Rats Spectrum Analysis

Chemicals

Benz(a)Anthracenes Ethers, Cyclic

Authors & Affiliations

1 authors, click to expand affiliations / ORCID

Sims P

References (18)

18 references, click to expand

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Article Info

Journal

The Biochemical journal

Abbr.

Biochem J

ISSN

0264-6021

DOI

10.1042/bj1250159

Published

1971-11-00

Pages

159-68

Language

English

Region

England

NLM ID

2984726R

PMCID

PMC1178036

Subset

External Links

PubMed source DOI: 10.1042/bj1250159 PMC Full Text View journal details

Analysis Services

Epoxy derivatives of aromatic polycyclic hydrocarbons. The preparation of benz( )anthracene 8,9-oxide and 10,11-dihydrobenz( )anthracene 8,9-oxide and their metabolism by rat liver preparations.

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