Molecular mechanism of chemical modification of cellular nucleic acid bases by 4-hydroxyaminoquinoline 1-oxide.
The O-acyl derivative of 4-hydroxyaminoquinolone, the proposed ultimate metabolite in carcinogenesis by the parent compound, was proposed to undergo a nitrogen-oxygen heterolysis to produce three types of reaction intermediates: a nitrenium, a carbonium, and nitrene intermediates, which were considered to give N(4)-substituted 4-aminoquinoline 1-oxide (4-AQO), 3-substituted 4-AQO, and 4-AQO, respectively, in reactions with nucleophiles including nucleic acid  bases. Chemical modification of cellular DNA by this carcinogen is discussed.
D015108:4-Hydroxyaminoquinoline-1-oxide / Q000378:metabolism*; D000634:Aminoquinolines / Q000378:metabolism*; D000818:Animals; D001711:Biotransformation; D004247:DNA / Q000378:metabolism*; D005609:Free Radicals; D012313:RNA / Q000378:metabolism*
D000634:Aminoquinolines; D005609:Free Radicals; D015108:4-Hydroxyaminoquinoline-1-oxide; D012313:RNA; D004247:DNA