title: Exploration of binding of bisphenol A and its analogues with calf thymus DNA by optical spectroscopic and molecular docking methods.
abstract: Bisphenol A and its analogues have carcinogenic potentials and toxicities. However, there are lacks of studies elucidating gene toxic interactions of bisphenols with DNA. In this work, the binding modes of five bisphenol compounds with calf thymus DNA were characterized. The multi-spectroscopic experimental results indicated that the fluorescence quenching of bisphenols by calf thymus DNA point to groove binding. The ultraviolet visible and circular dichroism spectral data displayed that bisphenols partly induced conformational changes of calf thymus DNA. In addition, the binding constants of bisphenol A, diphenolic acid, bisphenol AF, bisphenol AP, bisphenol fluorine with calf thymus DNA obtained from fluorescence emission spectra were 1.09×10(4), 3.65×10(4), 4.46×10(4), 1.69×10(4), 4.49×10(4)Lmol(-1) at 298.15K, which indicated that the multi-noncovalent binding forces were involved in the binding processes. In silico investigations indicated that DNA has the preferable binding sites binding with bisphenols by minor groove binding and electrons transfer from DNA bases to bisphenols occurred. In addition, the structural differences of these five bisphenols partly affected the binding ability of them with DNA.
authors.affiliation: Jiangsu Provincial Key Laboratory of Coastal Wetland Bioresources and Environmental Protection, Yancheng City, Jiangsu Province 224002, People's Republic of China; Institute of Applied Chemistry and Environmental Engineering, Yancheng Teachers University, Yancheng City, Jiangsu Province 224002, People's Republic of China. Electronic address: wyqing76@126.com.
authors.forename: Yan-Qing
authors.initials: YQ
authors.lastname: Wang
authors.affiliation: Jiangsu Provincial Key Laboratory of Coastal Wetland Bioresources and Environmental Protection, Yancheng City, Jiangsu Province 224002, People's Republic of China; Institute of Applied Chemistry and Environmental Engineering, Yancheng Teachers University, Yancheng City, Jiangsu Province 224002, People's Republic of China.
authors.forename: Hong-Mei
authors.initials: HM
authors.lastname: Zhang
mesh_terms: D000818:Animals; D001559:Benzhydryl Compounds / Q000737:chemistry* / Q000378:metabolism*; D002417:Cattle; D004247:DNA / Q000737:chemistry / Q000378:metabolism*; D062105:Molecular Docking Simulation; D009690:Nucleic Acid Conformation; D010636:Phenols / Q000737:chemistry* / Q000378:metabolism*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013816:Thermodynamics; D000098826:Bisphenol A Compounds
chemical_list: D001559:Benzhydryl Compounds; D004247:DNA; D010636:Phenols; C427203:calf thymus DNA; C006780:bisphenol A; D000098826:Bisphenol A Compounds
keywords: Binding mode; Bisphenols; DNA; Molecular modeling; Spectrum