N2-GUANYL AND N6-ADENYL ARYLATION OF CHICKEN ERYTHROCYTE DNA BY THE ULTIMATE CARCINOGEN OF 4-NITROQUINOLINE 1-OXIDE
- 1 April 1986
- journal article
- research article
- Vol. 46 (4) , 1858-1863
Abstract
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. Galiegue-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.This publication has 20 references indexed in Scilit:
- Mechanisms of action of carcinogenic aromatic amines: An investigation using mutagenesis in bacteriaChemico-Biological Interactions, 1979
- Evaluation of the Mutagenicity and DNA-Modifying Activity of Carcinogens and Noncarcinogens in Microbial Systems2JNCI Journal of the National Cancer Institute, 1979
- Reaction products of the carcinogen N-hydroxy-4-acetylamino-4′-fluorobiphenyl with DNA in liver and kidney of the ratChemico-Biological Interactions, 1978
- SOME CURRENT PERSPECTIVES ON CHEMICAL CARCINOGENESIS IN HUMANS AND EXPERIMENTAL-ANIMALS - PRESIDENTIAL-ADDRESS1978
- Application of the change in partition coefficient with pH to the structure determination of alkyl substituted guanosinesBiochemical and Biophysical Research Communications, 1976
- Identification of the persistently bound form of the carcinogen N-acetyl-2-aminofluorene to rat liver DNA in vivoChemico-Biological Interactions, 1976
- Californium-252 Plasma Desorption Mass SpectroscopyScience, 1976
- Chemical structure of QAII, one of the covalently bound adducts of carcinogenic 4-nitroquinoline 1-oxide with nucleic acid bases of cellular nucleic acids.CHEMICAL & PHARMACEUTICAL BULLETIN, 1975
- METABOLISM OF 4-NITROQUINOLINE-1-OXIDE A CARCINOGEN .3. AN ENZYME CATALYZING CONVERSION OF 4-NITROQUINOLINE-1-OXIDE TO 4-HYDROXYAMINOQUINOLINE-1-OXIDE IN RAT LIVER AND HEPATOMAS1966
- METABOLISM OF 4-NITROQUINOLINE 1-OXIDE .2. IN VIVO CONVERSION OF SUBCUTANEOUSLY INJECTED 4-NITROQUINOLINE 1-OXIDE TO 4-AMINOQUINOLINE 1-OXIDE AND 4-HYDROXYQUINOLINE 1-OXIDE IN RATS1966