Adducts from the reaction of O,O'-diacetyl or O-acetyl derivatives of the carcinogen 4-hydroxyaminoquinoline 1-oxide with purine nucleosides.
The diacetyl derivative of 4-hydroxyaminoquinoline 1-oxide (4-HAQO), the proximate carcinogen of 4-nitroquinoline 1-oxide, was reacted in vitro with purine nucleosides to give five adducts (three with guanosine and two with adenosine). The same nucleoside modifications were also obtained with a monoacetyl derivative of 4-HAQO which is probably 4-acetoxyaminoquinoline 1-oxide. The structure of the major adduct (the so-called dG III) was identified as N-(deoxyguanosin-C8-yl)-4-aminoquinoline 1-oxide. The isolation of this adduct from the 4-HAQO-modified DNA in vivo provides strong support for the hypothesis that the acetyl derivatives of 4-HAQO constitute a good model for the ultimate carcinogen.
D000634:Aminoquinolines / Q000032:analysis / Q000302:isolation & purification*; D000818:Animals; D002273:Carcinogens; D002460:Cell Line; D002851:Chromatography, High Pressure Liquid; D004247:DNA; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D011684:Purine Nucleosides; D051381:Rats
D000634:Aminoquinolines; D002273:Carcinogens; D011684:Purine Nucleosides; C027915:O,O-diacetyl-4-hydroxyaminoquinoline 1-oxide; C032982:4-acetoxyaminoquinoline 1-oxide; C032983:N-(deoxyguanosin-C(8)-yl)-4-aminoquinoline 1-oxide; D004247:DNA; D003849:Deoxyguanosine