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Citation
Tags
HERO ID
201792
Reference Type
Journal Article
Title
Microsomal biphenyl hydroxylation: The formation of 3-hydroxybiphenyl and biphenyl catechol
Author(s)
Billings, RE; Mcmahon, RE
Year
1978
Is Peer Reviewed?
1
Journal
Molecular Pharmacology
ISSN:
0026-895X
EISSN:
1521-0111
Report Number
HEEP/78/09121
Volume
14
Issue
1
Page Numbers
145-154
Language
English
PMID
625282
Abstract
3-Hydroxybiphenyl has been identified as a metabolite of biphenyl incubated with liver microsomes. Liver microsomes from hamster, mouse, and rabbit form 3-hydroxybiphenyl as well as 2-hydroxybiphenyl and 4-hydroxybiphenyl. The ratio of 2-hydroxybiphenyl to 3-hydroxybiphenyl is about 2:l with hamster and rabbit microsomes and 1:l with mouse microsomes. The major metabolite in all three species is 4-hydroxybiphenyl, but its relative amount also depends upon the species. Control rat liver microsomal hydroxylation of biphenyl yields 4-hydroxybiphenyl almost exclusively. 3-Methylcholanthrene or β-napthoflavone treatment of rats preferentially induces 2-hydroxybiphenyl formation, whereas increased amounts of 3- and 4-hydroxybiphenyl are formed after administration of phenobarbital. These results indicate that 3-hydroxybiphenyl is formed by a pathway different from that of either 2- or 4-hydroxybiphenyl. The existence of isotope effects for 3-hydroxybiphenyl formation but not for 2- or 4-hydroxybiphenyl formation from perdeuterobiphenyl suggests that this hydroxylation occurs at least partially via a direct hydroxylation pathway. In addition to the monohydroxylated products of biphenyl, the microsomal oxidation of biphenyl yields the catechol, 3,4-dihydroxybiphenyl. This same catechol is produced by the hydroxylation of either 3- or 4-hydroxybiphenyl. Studies with 18O suggest that 3,4-dihydroxybiphenyl is formed from biphenyl via two consecutive hydroxylations.
Keywords
Animals; Biphenyl Compounds/*metabolism; Carcinogens/pharmacology; Catechols/*metabolism; Cricetinae; Cytochrome P-450 Enzyme System/biosynthesis; Enzyme Induction/drug effects; Hydroxylation; Male; Mass Spectrometry; Mesocricetus; Mice; Microsomes, Liver/*metabolism; Rabbits; Rats
Tags
IRIS
•
Biphenyl
Considered
Cited References
Toxicokinetics
•
PCBs
Cited (Nov 2012)
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