N2-guanyl and N6-adenyl arylation of chicken erythrocyte DNA by the ultimate carcinogen of 4-nitroquinoline 1-oxide

Great quantities of chicken erythrocyte DNA with high levels of modification were obtained in vitro by reaction with 4-acetoxyaminoquinoline 1-oxide, a model ultimate carcinogen of 4-nitroquinoline 1-oxide. After enzymatic hydrolysis of the modified DNA, the three main adducts were separated and iso...

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Bibliographic Details
Published in:Cancer research (Chicago, Ill.) Ill.), 1986-04, Vol.46 (4), p.1858-1863
Main Authors: GALIEGUE-ZOUITINA, S, BAILLEUL, B, GINOT, Y.-M, VIGNY, P, LOUCHEUX-LEFEBVRE, M.-H
Format: Article
Language:English
Subjects:
4-Nitroquinoline-1-oxide - toxicity
Animals
Biological and medical sciences
Carcinogenesis, carcinogens and anticarcinogens
Chemical agents
Chickens
Chromatography, High Pressure Liquid
DNA
Erythrocytes - analysis
Magnetic Resonance Spectroscopy
Mass Spectrometry
Medical sciences
Mutation
Nitroquinolines - toxicity
Tumors
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Summary:Great quantities of chicken erythrocyte DNA with high levels of modification were obtained in vitro by reaction with 4-acetoxyaminoquinoline 1-oxide, a model ultimate carcinogen of 4-nitroquinoline 1-oxide. After enzymatic hydrolysis of the modified DNA, the three main adducts were separated and isolated by semipreparative high performance liquid chromatography. These three adducts were already characterized in vivo and in vitro in our previous work (S. Galiègue-Zouitina et al., Cancer Res., 45: 520-525, 1985). The structure of one of them was previously identified as N-(deoxyguanosin-8-yl)-4-aminoquinoline 1-oxide (B. Bailleul et al., Cancer Res., 41: 4559-4565, 1981). In this paper we have identified by mass spectroscopy and nuclear magnetic resonance the structures of the two other main adducts as 3-(deoxyguanosin-N2-yl)-4-aminoquinoline 1-oxide and 3-(deoxyadenosin-N6-yl)-4-aminoquinoline 1-oxide, respectively.
ISSN:0008-5472
1538-7445