Comparative studies on the metabolism of quinoline and isoquinoline: Molecular basis for differences in mutagenic and carcinogenic activities

Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28 Flavouring Group Evaluation 24, Revision 1 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)

“…In addition the metabolites 2-hydroxyquinoline, 3-hydroxyquinoline and quinoline-N-oxide were found in less quantities. Incorporation of the epoxide hydrolase inhibitor, 3,3,3trichloropropyleneoxide (TCPO), into the reaction mixture was reported not to affect the metabolism profile of quinoline (LaVoie et al, 1983a). In another study the metabolism of quinoline was studied in hepatic microsomal fractions from rat.…”

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 24 (FGE.24): Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28 (Commis

“…In addition the metabolites 2-hydroxyquinoline, 3-hydroxyquinoline and quinoline-N-oxide were found in less quantity. Incorporation of the epoxide hydrolase inhibitor, 3,3,3-trichloropropyleneoxide (TCPO), into the reaction mixture was reported not to affect the metabolism profile of quinoline (LaVoie et al, 1983a). In another study the metabolism of quinoline was studied in hepatic microsomal fractions from rat.…”

Non-enzymatic hydration, amine addition, and oxidation reactions of aza-arene oxides

“…Quinoline is a common environmental pollutant which is known to be both mutagenic and carcinogenic,l and to yield a range of mammalian metabolites including quinoline N-oxide,lJ quinoline 5,6-oxide (1B) ,3 trans-5,6-dihydroxy-5,6dihydroquinoline (2B) ,1-3 and several quinolinols (2-, 3-, 6-, 8-hydroxyquinolines) . 1,234 Members of the polycyclic aromatic hydrocarbon (PAH) and azapolycyclic aromatic hydrocarbon (APAH) series have been found to follow common metabolic pathways in mammalian systems (Scheme 1).5--7 All the isolated metabolites emanate from the initially formed arene oxide metabolite (1, formed in step c may undergo non-enzymatic addition reactions with amines,5 to form amino-triols (4) (step d), the uncatalysed addition of amines to type (1) arene oxides has not previously been observed (A1203-catalysed addition of primary amines to non-K region arene oxides has been observed) . 8 The present communication reports on the non-enzymatic hydration (step b), amine addition (step g), and epoxidation (step f) or N-oxidation (1B + l D , 1C + 1E) reactions of arene oxides (1) in the polycyclic aza-arene series [exemplified by the 5,6-(1B) and 7,8-arene oxides (1C) of quinoline].…”