title: Study on the binding interaction between perfluoroalkyl acids and DNA.
abstract: Perfluoroalkyl acids (PFAAs) are carcinogens, and elucidating their DNA binding properties is crucial for understanding PFAA genotoxicity. We have investigated the binding mode and affinity of five PFAAs to seven DNA molecules using fluorescence displacement and molecular docking analysis. DNA conformational changes upon PFAA binding were also examined by circular dichroism (CD). The data revealed that DNA intercalation was the dominant interaction mode of the PFAAs; however, these molecules also bound to grooves. The dissociation constants for the PFAAs ranged between 0.11 and 1,217.14 μM, and between 3.46 and 2,141.21 μM for DNA intercalation and groove binding, respectively. PFAAs that contain longer carbon chains had stronger DNA intercalation affinities. Binding to DNA was stronger for perfluoroalkyl sulfonates than for perfluorcarboxyl acids that contain the same number of carbons. This observation is postulated to arise from the presence of more fluorine and oxygen atoms in perfluoroalkyl sulfonates acting as hydrogen bond donors that facilitate stronger DNA intercalation. The binding of the PFAAs to DNA showed some CT-DNA sequence selectivity. Molecular docking analysis confirmed the DNA binding mode and affinities of the PFAAs. CD analysis revealed that the PFAAs weakened DNA base stacking and loosened DNA helicity. The present study has improved our understanding of the formation of PFAA-DNA adducts.
authors: AQSIQ Key Laboratory of Drug Detection, Fujian International Travel Healthcare Center, Fujian Entry-Exit Inspection and Quarantine Bureau of P.R.C., Fujian, 350001, China.
authors: Jie
authors: J
authors: Cao
authors: Yin
authors: Y
authors: Wei
authors: Yan
authors: Y
authors: Cheng
authors: Liang-Hong
authors: LH
authors: Guo
mesh_terms: D001483:Base Sequence; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry / Q000378:metabolism*; D004249:DNA Damage; D004785:Environmental Pollutants / Q000737:chemistry / Q000378:metabolism*; D005466:Fluorocarbons / Q000737:chemistry / Q000378:metabolism*; D008958:Models, Molecular; D009153:Mutagens / Q000737:chemistry / Q000378:metabolism
chemical_list: D004785:Environmental Pollutants; D005466:Fluorocarbons; D009153:Mutagens; D004247:DNA
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