Binding of benzidine, N-acetylbenzidine, N, N'-diacetylbenzidine and Direct Blue 6 to rat liver DNA.
Studies were performed to assess covalent binding of [3H]benzidine, [14C]N-acetylbenzidine, [14C]N, N'-diacetylbenzidine, and the benzidine-derived azo dye Direct Blue 6 to rat hepatic DNA. Following IP injection into male Sprague-Dawley rats, benzidine and N-acetylbenzidine bound to liver DNA to yield the same adduct: N-(deoxyguanosin-8-yl)-N'-acetylbenzidine. The isomeric N-(deoxyguanosin-8-yl)-N-acetylbenzidine and the deacetylated adduct N-(deoxyguanosin-8-yl) benzidine were also synthesized, but neither of these adducts was detected in vivo. Injection of N,N'-diacetylbenzidine resulted in only barely detectable binding which was insufficient for adduct analysis. [3H]Direct Blue 6 was administered to male Wistar rats either by IP injection or by gavage. In both instances, Direct Blue 6 bound covalently to liver DNA; however, binding occurred at a much higher level in the IP injected animals. With IP injected animals, high pressure liquid chromatographic analysis indicated that approximately 70% of the radioactivity was associated with N-(deoxyguanosin-8-yl) benzidine.
D000818:Animals; D001391:Azo Compounds / Q000378:metabolism; D001560:Benzidines / Q000378:metabolism*; D001665:Binding Sites; D004247:DNA / Q000378:metabolism*; D008099:Liver / Q000378:metabolism*; D008297:Male; D051381:Rats; D011919:Rats, Inbred Strains
D001391:Azo Compounds; D001560:Benzidines; C017261:direct blue 6; C007291:N,N'-diacetylbenzidine; D004247:DNA; C034938:N-acetylbenzidine