title: Characterization of the groove binding between di-(2-ethylhexyl) phthalate and calf thymus DNA.
abstract: In this study, the interaction between di-(2-ethylhexyl) phthalate (DEHP) and calf thymus DNA (ctDNA) was investigated by a combination of multispectroscopic methods, chemometrics algorithm, cyclic voltammetry and molecular simulation. The concentration profiles of the components obtained from resolving the UV-vis absorption data by multivariate curve resolution-alternating least-squares (MCR-ALS) provided a basic evidence for the formation of DEHP-ctDNA complex. Furthermore, the groove binding of DEHP to ctDNA was evidenced by the results from iodide quenching effect, single-stranded DNA quenching effect, melting studies, viscosity measurements and cyclic voltammetry. The binding constant of the complex was in the order of magnitudes of 104Lmol-1, and hydrophobic forces were inferred to drive the binding process. Analysis of Fourier transform infrared spectra suggested that DEHP preferentially bound to A-T rich region of ctDNA in the minor groove, and these results further confirmed by molecular docking. The circular dichroism spectra indicated that DEHP induced a decrease in base stacking degree and an increase in right-handed helicity of ctDNA, but did not cause a significant damage in DNA. This study may improve the understanding of interaction between DEHP and ctDNA and help evaluate the toxicological effect of DEHP.
authors.affiliation: State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, China.
authors.forename: Song
authors.initials: S
authors.lastname: Li
authors.affiliation: State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, China.
authors.forename: Junhui
authors.initials: J
authors.lastname: Pan
authors.affiliation: State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, China. Electronic address: gwzhang@ncu.edu.cn.
authors.forename: Guowen
authors.initials: G
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, China.
authors.forename: Jianjian
authors.initials: J
authors.lastname: Xu
authors.affiliation: State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, China; New Zealand Institute of Natural Medicine Research, 8 Ha Crescent, Manukau 2104, Auckland, New Zealand.
authors.forename: Deming
authors.initials: D
authors.lastname: Gong
mesh_terms: D000818:Animals; D002417:Cattle; D004247:DNA / Q000737:chemistry* / Q000378:metabolism*; D053837:DNA Cleavage / Q000187:drug effects; D004051:Diethylhexyl Phthalate / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D004563:Electrochemistry; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D009994:Osmolar Concentration; D013816:Thermodynamics
chemical_list: D004247:DNA; C427203:calf thymus DNA; D004051:Diethylhexyl Phthalate
keywords: Calf thymus DNA; Di-(2-ethylhexyl) phthalate; MCR–ALS algorithm; Molecular simulation