Metabolism of mutagenicity-deprived 3-fluoroquinoline: comparison with mutagenic quinoline.
3-Fluorinated quinoline (3FQ), a non-mutagenic derivative of the potent mutagen quinoline, was metabolized with a microsomal enzyme fraction isolated from the 3-methylcholanthrene-treated rat liver. The metabolites were 3-fluoro-5,6-dihydroquinoline-5,6-trans-diol (72%), 3-fluoroquinoline 1-oxide (6%), 3-fluoro-5,6-dihydroquinoline-5,6-cis-epoxide (1%), and 4 unidentified metabolites (11%). Since this metabolic pattern is similar to that obtained with unfluorinated quinoline, the epoxidation of the benzene moieties of quinoline and 3-fluoroquinoline is most likely a detoxication process and not mutagenic activation.
Saeki
K
K
Faculty of Pharmaceutical Sciences, Nagoya City University, Japan.
Takahashi
K
K
Kawazoe
Y
Y
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D006912:Hydroxyquinolines / Q000378:metabolism*; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism; D009153:Mutagens / Q000378:metabolism*; D010084:Oxidation-Reduction; D011804:Quinolines / Q000378:metabolism*; D051381:Rats; D017207:Rats, Sprague-Dawley; D013056:Spectrophotometry, Ultraviolet
D006912:Hydroxyquinolines; D009153:Mutagens; D011804:Quinolines; C082976:3-fluoro-5,6-dihydroquinoline 5,6-diol; C082975:5-fluoroquinoline; C082974:3-fluoroquinoline