Document Detail

Identification of the metabolites of benzo[f]quinoline and benzo[h]quinoline formed by rat liver homogenate.
MedLine Citation:
PMID:  6883636     Owner:  NLM     Status:  MEDLINE    
Benzo[f]quinoline and benzo[h]quinoline are widespread environmental pollutants which have been found to be mutagenic. The metabolism of benzo[f]quinoline and benzo[h]quinoline was investigated using a liver homogenate from Aroclor-pretreated rats. The metabolites of benzo[f]quinoline which were identified were 7,8-dihydroxy-7,8-dihydrobenzo[f]quinoline, 9,10-dihydroxy-9,10-dihydrobenzo[f]quinoline, 7-hydroxybenzo[f]quinoline, and benzo[f]quinoline-N-oxide. Metabolism studies on benzo[f]quinoline performed in the presence of the epoxide hydratase inhibitor, 3,3,3-trichloropropylene oxide, demonstrated that the formation of both of these dihydrodiols can be inhibited. The major metabolites of benzo[h]quinoline were identified as 5,6-dihydroxy-5,6-dihydrobenzo[h]quinoline and 7,8-dihydroxy-7,8-dihydrobenzo[h]quinoline. Benzo[h]quinoline-N-oxide was not detected as a metabolite. In the presence of an epoxide hydratase inhibitor, the major metabolites of benzo[h]quinoline were 5,6-epoxybenzo[h]quinoline and 7-hydroxybenzo[h]quinoline. The difference in the metabolism to N-oxides observed between benzo[h]quinoline and benzo[f]quinoline is consistent with previous observations in which sterically hindered aromatic ring nitrogen compounds such as benzo[h]quinoline are more resistant to N-oxide formation. The nitrogen atom of these aza-arenes with its lone pair of electrons has a significant influence on sites at which dihydrodiols are formed. The data suggest that the aromatic ring nitrogen of these azaphenanthrenes has an effect similar to that of a methyl substituent in directing their metabolic oxidation.
E J LaVoie; E A Adams; D Hoffmann
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Carcinogenesis     Volume:  4     ISSN:  0143-3334     ISO Abbreviation:  Carcinogenesis     Publication Date:  1983 Sep 
Date Detail:
Created Date:  1983-10-08     Completed Date:  1983-10-08     Revised Date:  2009-11-19    
Medline Journal Info:
Nlm Unique ID:  8008055     Medline TA:  Carcinogenesis     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  1133-8     Citation Subset:  IM    
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MeSH Terms
Chromatography, High Pressure Liquid
Cytosol / metabolism
Epoxide Hydrolases / metabolism
Liver / metabolism*
Mass Spectrometry
Microsomes, Liver / metabolism
Mutagens / metabolism*
Quinolines / metabolism*
Rats, Inbred F344
Spectrophotometry, Ultraviolet
Structure-Activity Relationship
Reg. No./Substance:
0/Mutagens; 0/Quinolines; 230-27-3/benzo(h)quinoline; 85-02-9/benzo(f)quinoline; EC 3.3.2.-/Epoxide Hydrolases

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