Detail of "324-93-6"

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Reaction products of the carcinogen N-hydroxy-4-acetylamino-4'-fluorobiphenyl with DNA in liver and kidney of the rat

Reaction products of the carcinogen N-hydroxy-4-acetylamino-4'-fluorobiphenyl with DNA in liver and kidney of the rat. Kriek, E.; Hengeveld, G. M. (Chem. Carcinog. Div., Netherlands Cancer Inst., Amsterdam, Neth.). Chem.-Biol. Interact., 21(2-3), 179-201 (English) 1978. CODEN: CBINA8. ISSN: 0009-2797. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) The binding of 4-acetylamino-4'-fluorobiphenyl (I) [398-32-3] and 4-amino-4'-fluorobiphenyl (II) [324-93-6] residues to rat liver and kidney DNA in vivo was studied at different periods of time after administration of 3H-labeled N-hydroxy-I [67764-17-4] at of 5 and 25 mg/kg . N-(deoxyguanosine-8-yl)-II decompn. products, a product with similar chromatog. and chem. properties as 3-(deoxyguanosin-N2-yl)acetylaminofluorene [61370-84-1], and a product that cochromatog. with the marker N-(deoxyguanosin-8-yl)-I [67764-18-5] were obtained from the DNA prepns. from both organs following hydrolysis and Sephadex chromatog. Kinetic studies revealed that the latter product was removed rapidly from liver and kidney DNA at equal rates (t1/2; 2 days). Approx. 80% of the total radioactivity bound to DNA consisted of deacetylated material, which was removed at a much slower rate (t1/2; 10 days) in both organs. An initial rapid removal of all products in kidney during the 1st 7 days (t1/2; 3.3 days) at dose levels of 25 mg/kg was probably due to toxic effects on the kidneys, because this phenomenon was not obsd. at dose levels of 5 mg/kg. The synthetic ester N-KOSO3-I [67764-19-6] was at least twice as reactive towards L-methionine [63-68-3] and guanosine as compared to the corresponding acetylaminobiphenyl deriv., but had 40% of the reactivity of N-acetoxyacetylaminofluorene under similar conditions. The new compds. 3-methylmercapto-4-acetylamino-4'-fluorobiphenyl [67764-12-9] and N-(deoxyguanosin-8-yl)-4-acetylamino-4'-fluorobiphenyl were characterized by means of their NMR and mass spectra. Attempts to devise an unambiguous synthesis for 3-(deoxyguanosin-N2-yl)arylamides were unsuccessful.