ADDUCTS FROM THE REACTION OF O,O'-DIACETYL OR O-ACETYL DERIVATIVES OF THE CARCINOGEN 4-HYDROXYAMINOQUINOLINE 1-OXIDE WITH PURINE NUCLEOSIDES

  • 1 January 1981
    • journal article
    • research article
    • Vol. 41 (11), 4559-4565
Abstract
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 5 adducts (3 with guanosine and 2 with adenosine). The same nucleoside modifications were 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.