ADDUCTS FROM INVIVO ACTION OF THE CARCINOGEN 4-HYDROXYAMINOQUINOLINE 1-OXIDE IN RATS AND FROM INVITRO REACTION OF 4-ACETOXYAMINOQUINOLINE 1-OXIDE WITH DNA AND POLYNUCLEOTIDES

  • 1 January 1985
    • journal article
    • research article
    • Vol. 45  (2) , 520-525
Abstract
In vivo 4-hydroxyamino[2-3H]quinoline-1-oxide-modified DNA and in vitro 4-acetoxyamino[2-3H]quinoline-1-oxide-modified DNA were enzymatically hydrolyzed, and the hydrolysates were analyzed by high-performance liquid chromatography. The 2 patterns were compared, and all of the high-performance liquid chromatography peaks which were recovered from in vivo-modified DNA were present in the hydrolysate of in vitro-modified DNA. The in vitro-4-acetoxyamino[2-3H]quinoline-1-oxide-modified DNA was used to investigate the quinoline-purine adducts which are characteristics of the mode of action of the carcinogen 4-nitroquinoline-1-oxide. By comparison with the enzymatic hydrolysates of 4-acetoxyamino[2-3H]-quinoline-1-oxide-modified covalent poly(deoxyadenylate-deoxythymidylate) poly(deoxyadenylate-deoxythymidylate) and covalent poly(deoxyguanylate-deoxycytidylate) poly(deoxyguanylate-deoxycytidylate) 3 nitroquinoline adducts were enumerated on the modified DNA. One of them was previously characterized as a C8-guanyl adduct. The 2 other are a guanine and an adenine adduct, respectively. A quinoline derivative was identified in the hydrolysates of the in vivo- and in vitro-modified DNA as 4-aminoquinoline-1-oxide, the origin of which was postulated to be a degradation compound of one (or more) adduct(s). The presence of 2 degradation compounds of the C8-guanyl adduct was shown in mild alkaline conditions. An imidazole ring-opened form was suspected.

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