Arylamidation and arylation by the carcinogen N-2-fluorenylacetamide: a sensitive and rapid radiochemical assay.
N-acetoxy-N-arylacetamides, which are generally considered as an ultimate carcinogenic form of the corresponding N-arylacetamides, react with the cellular macromolecules (nucleic acids, proteins, etc.) to give two types of adducts: (I) arylamidation and (II) arylation addition products. In this paper, we present a radiochemical determination of the amount of N-2-fluorenylacetamide bound to DNA via arylamidation or arylation, respectively. This assay is based upon the difference of stability under weak alkali hydrolysis conditions (0.1 N NaOH, 75 degrees C, 2 h) of the specifically 14C-labeled N-acetyl group of the N-2-fluorenylacetamide residue linked to the macromolecule either via arylamidation or arylation. Native DNA which has been reacted with N-acetoxy-N-2-[14C]acetylaminofluorene exhibits 16% of the fluorene adducts linked to the bases via arylation. On the other hand, denatured DNA reacts with the fluorene derivative to give almost only arylamidation addition products.
Institut de Biologie Moleculaire et Cellulaire du CNRS, Groupe de Biophysique, Strasbourg, France.
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Fuchs
D015073:2-Acetylaminofluorene / Q000032:analysis* / Q000633:toxicity; D002273:Carcinogens / Q000032:analysis* / Q000633:toxicity; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000737:chemistry; D018736:DNA Adducts / Q000032:analysis*; D009691:Nucleic Acid Denaturation; D011854:Radiochemistry; D013056:Spectrophotometry, Ultraviolet
D002273:Carcinogens; D018736:DNA Adducts; D004247:DNA; D015073:2-Acetylaminofluorene