title: Binding of 2-acetylaminofluorene to DNA.
abstract: 2-Acetylaminofluorene (2-AAF) is a carcinogenic and mutagenic derivative of fluorene. It is used as a biochemical tool in the study of carcinogenesis. Studies have shown that it induces tumors in a number of species in the liver, bladder, and kidney. It is thought that 2-AAF-DNA adduct formation leads to mutation, and eventually tumor formation. The aim of this study was to examine the interactions of AAF with calf-thymus DNA in aqueous solution at physiological conditions, using constant DNA concentration (12.5 mM) and various AAF/polynucleotide (phosphate) ratios of 1/120, 1/80, 1/40, 1/20, 1/10, 1/5, 1/2, and 1/1. Fourier transform infrared and UV-visible spectroscopic methods and molecular modeling were used to determine the ligand binding mode, the binding constant, and the stability of AAF-DNA complexes in aqueous solution. Spectroscopic evidence showed both intercalation and external binding of AAF to DNA with an overall binding constant of K(AAF-DNA) = 2.33 × 10(7) M(-1). 2-AAF induced a partial B to A-DNA transition and DNA aggregation was observed at high AAF content.
authors.affiliation: Department of Chemistry, Central Tehran Branch (IAUCTB), Islamic Azad University, Tehran, Iran. drnafisi@yahoo.com
authors.forename: Shohreh
authors.initials: S
authors.lastname: Nafisi
authors.forename: Mahyar
authors.initials: M
authors.lastname: Bonsaii
authors.forename: Valerie
authors.initials: V
authors.lastname: Alexis
authors.forename: James
authors.initials: J
authors.lastname: Glick
mesh_terms: D015073:2-Acetylaminofluorene / Q000378:metabolism* / Q000494:pharmacology; D000818:Animals; D001483:Base Sequence; D002273:Carcinogens / Q000378:metabolism* / Q000494:pharmacology; D002417:Cattle; D004247:DNA / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D008958:Models, Molecular; D009690:Nucleic Acid Conformation / Q000187:drug effects; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D002273:Carcinogens; D004247:DNA; D015073:2-Acetylaminofluorene