title: Study on the mechanism of action between dimethyl phthalate and herring sperm DNA at molecular level.
abstract: Dimethyl phthalate (DMP), a typical phthalic acid ester, is widespread in the environment and causes extensive concern due to its adverse effects on human health. To understand the genotoxicity of DMP at molecular level, the toxic interaction of DMP with herring sperm (hs) deoxyribonucleic acid (DNA; hs-DNA) was investigated in vitro under simulated physiological conditions using multi-spectroscopic techniques and a molecular modeling method. The results of Ultraviolet-Visible absorption spectroscopy, fluorescence emission spectroscopy, and circular dichroism spectra indicated that DMP interacts with hs-DNA in a groove-binding mode that changes the double helical structure of DNA. The binding constant and the number of binding sites calculated from the fluorescence quenching data were 565.718 L mol(-1) and 0.7872, respectively. A molecular modeling study revealed that DMP tends to bind with DNA in the A-T-rich regions of minor groove and that hydrogen bonding and van der Waals forces play main roles in the interaction. This research can help to elucidate the mechanism of DMP toxicity in vivo.
authors.affiliation: a State Key Laboratory of Urban Water Resource and Environment, Harbin Institute of Technology , Harbin , China.|b School of Marine Science and Technology, Harbin Institute of Technology at Weihai , Weihai , China.
authors.forename: Zhenxing
authors.initials: Z
authors.lastname: Chi
authors.affiliation: b School of Marine Science and Technology, Harbin Institute of Technology at Weihai , Weihai , China.
authors.forename: Donglin
authors.initials: D
authors.lastname: Wang
authors.affiliation: a State Key Laboratory of Urban Water Resource and Environment, Harbin Institute of Technology , Harbin , China.|b School of Marine Science and Technology, Harbin Institute of Technology at Weihai , Weihai , China.
authors.forename: Hong
authors.initials: H
authors.lastname: You
mesh_terms: D000818:Animals; D001665:Binding Sites / Q000187:drug effects; D002942:Circular Dichroism; D004247:DNA / Q000187:drug effects*; D005399:Fishes / Q000254:growth & development*; D005453:Fluorescence; D006801:Humans; D006860:Hydrogen Bonding / Q000187:drug effects; D008297:Male; D008958:Models, Molecular; D010795:Phthalic Acids / Q000737:chemistry* / Q000633:toxicity*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013094:Spermatozoa / Q000187:drug effects* / Q000254:growth & development*; D013816:Thermodynamics
chemical_list: D010795:Phthalic Acids; C032279:phthalic acid; D004247:DNA
keywords: Multi-spectroscopic techniques; dimethyl phthalate; herring sperm DNA; interaction mechanism; molecular modeling