title: Study on the interaction of anthracenyl-methyl homospermidine conjugate (ANTMHspd) with DNA by spectroscopic methods.
abstract: The interaction between anthracenyl-methyl homospermidine conjugate (ANTMHspd) with herring sperm DNA was investigated by UV/vis absorption, fluorescent spectra, circular dichroism (CD) spectroscopy and1HNMR under physiological conditions (pH=7.4). The observed hypochromism effect and fluorescence quenching of ANTMHspd by DNA, and the displacement of EB from DNA-EB system by ANTMHspd suggested that ANTMHspd might interact with DNA by the combined mode of intercalation and groove binding. Further fluorescent tests at different temperatures revealed that the quenching mechanism was a static type. The quenching constant, binding constant and thermodynamic parameter obtained from fluorescence showed that the type of interaction force included mainly hydrogen bonding and van der Waals, which promoted the binding process. The CD test revealed that ANTMHspd could cause the B to A-like conformational change while ANTMHspd is not a typical DNA intercalator. The1H NMR tests showed that ANTMHspd partially intercalated DNA. The effect of NaCl and KI on ANTMHspd-DNA interaction provided additional evidences of intercalation. Molecular docking simulation was carried out and the docking model in silico suggested that the binding modes of ANTMHspd and DNA were groove binding and intercalation, with the anthracene moiety inserted in DNA base pairs and the polyamine chain embedded in the DNA groove.
authors.affiliation: Institute of Chemical Biology, Henan University, Kaifeng 475004, China.
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Tian
authors.affiliation: Institute of Chemical Biology, Henan University, Kaifeng 475004, China.
authors.forename: Luyao
authors.initials: L
authors.lastname: Zhao
authors.affiliation: Institute of Chemical Biology, Henan University, Kaifeng 475004, China.
authors.forename: Huanyang
authors.initials: H
authors.lastname: Dong
authors.affiliation: Institute of Chemical Biology, Henan University, Kaifeng 475004, China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Institute of Chemical Biology, Henan University, Kaifeng 475004, China.
authors.forename: Yijuan
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Institute of Chemical Biology, Henan University, Kaifeng 475004, China.
authors.forename: Qianlei
authors.initials: Q
authors.lastname: Ren
authors.affiliation: Institute of Chemical Biology, Henan University, Kaifeng 475004, China.
authors.forename: Shuangyu
authors.initials: S
authors.lastname: Shao
authors.affiliation: Institute of Chemical Biology, Henan University, Kaifeng 475004, China.
authors.forename: Yingying
authors.initials: Y
authors.lastname: Huang
authors.affiliation: Institute of Chemical Biology, Henan University, Kaifeng 475004, China.
authors.forename: Lina
authors.initials: L
authors.lastname: Song
authors.affiliation: The Key Laboratory of Natural Medicine and Immuno-Engineering, Henan University, Kaifeng 475004, China.
authors.forename: Tao
authors.initials: T
authors.lastname: Guo
authors.affiliation: The Key Laboratory of Natural Medicine and Immuno-Engineering, Henan University, Kaifeng 475004, China; Huaihe Clinical Institute, Henan University, Kaifeng 475004, China. Electronic address: 1322078049@qq.com.
authors.forename: Xuejun
authors.initials: X
authors.lastname: Xu
authors.affiliation: The Key Laboratory of Natural Medicine and Immuno-Engineering, Henan University, Kaifeng 475004, China. Electronic address: wcjsxq@henu.edu.cn.
authors.forename: Chaojie
authors.initials: C
authors.lastname: Wang
mesh_terms: D000818:Animals; D000873:Anthracenes / Q000737:chemistry* / Q000494:pharmacology; D001665:Binding Sites; D004247:DNA / Q000737:chemistry*; D007364:Intercalating Agents / Q000494:pharmacology; D062105:Molecular Docking Simulation; D009690:Nucleic Acid Conformation / Q000187:drug effects; D013057:Spectrum Analysis / Q000379:methods; D013095:Spermidine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000873:Anthracenes; D007364:Intercalating Agents; C529696:anthracenylmethyl homospermidine; D004247:DNA; D013095:Spermidine
keywords: ANTMHspd; DNA; Molecular docking; Spectroscopic methods