The effect of metal and substituent on DNA binding, cleavage activity, and cytotoxicity of new synthesized Schiff base ligands and Zn(II) complex

被引:25
|
作者
Asadi, Zahra [1 ]
Nasrollahi, Neda [1 ]
机构
[1] Shiraz Univ, Dept Chem, Fac Sci, Shiraz 71454, Iran
关键词
Metal-based drugs; Zn(II); Schiff base; DNA; CALF THYMUS DNA; COPPER(II) COMPLEXES; MOLECULAR DOCKING; ANTITUMOR-ACTIVITY; CELLULAR UPTAKE; COORDINATION; CU(II); PALLADIUM(II); DERIVATIVES; NICKEL(II);
D O I
10.1016/j.molstruc.2017.06.137
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
New water soluble Schiff base ligands [N,N'-bis(5-[(triphenylphosphonium percholorate)-methyl]sali-cylidine)-1,3-diamino-2-propanol] (L-1) and [N,N'-bis(salicylidine)-1,3-diamino-2-propanol] (L-2) and zinc (II) complex of L-1: [N,N'-bis{5-[(triphenylphosphonium percholorate)-methyl]salicylidine)-1,3-diamino-2-propanoWn(II) were synthesized and characterized by elemental analysis, FT-R, (HNMR)-H-1 and UV-Vis spectroscopy. In vitro DNA binding of the compounds were investigated by UV-Vis absorption spectroscopy, viscosity measurement, cyclic voltammetry, fluorescence spectroscopy, and gel electrophoresis. The present study aimed to investigate the effect of metal and substituent on DNA binding, cleavage activity and cytotoxicity of new synthesized Schiff base ligands and Zn(II) complex. The order of DNA binding affinity (K-b) calculated from the absorption spectroscopy was: ZnL1 > L-2 > L-1. Molecular docking studies explore more details on the mode of binding and binding energies. Although the compounds revealed strong DNA binding affinity but electrophoresis studies don't show any effects on the DNA structure and single or double strand breaks. The cytotoxicity experiments against human Hepatoma (HepG2) showed the order: L-1 > ZnL1 > L-2. (C) 2017 Elsevier B.V. All rights reserved.
引用
收藏
页码:582 / 593
页数:12
相关论文
共 50 条
  • [31] DNA Binding Activity of Functionalized Schiff Base Metal Complexes
    D'Anna, Luisa
    Marretta, Laura
    Froux, Aurane
    Rubino, Simona
    Butera, Valeria
    Spinello, Angelo
    Bonsignore, Riccardo
    Terenzi, Alessio
    Barone, Giampaolo
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2025, 28 (06)
  • [32] Synthesis and Evaluation of Cytotoxicity and Molecular Docking of New Symmetrical Macroacyclic Schiff Base Ligands and Their Ni(II) and Zn(II) Complexes
    Keypour, Hassan
    Rezaei, Mohammad Taher
    Hajari, Saadat
    Jamshidi, Mahdi
    Farida, Seyed Hamed Moazzami
    JOURNAL OF CHEMISTRY, 2023, 2023
  • [33] Synthesis, Characterization, DNA-binding Properties and DNA Cleavage of a New Ternary Copper(II) Complex with Mixed-ligands of Tridentate Schiff Base and 1,10-Phenanthroline
    Dong Jianfang
    Li Lianzhi
    Li Linwei
    Xu Tao
    Wang Daqi
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (02) : 259 - 266
  • [34] Synthesis of mononuclear copper(II) complexes of acyclic Schiff's base ligands: Spectral, structural, electrochemical, antibacterial, DNA binding and cleavage activity
    Jayamani, Arumugam
    Thamilarasan, Vijayan
    Sengottuvelan, Nallathambi
    Manisankar, Paramasivam
    Kang, Sung Kwon
    Kim, Young-Inn
    Ganesan, Vengatesan
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2014, 122 : 365 - 374
  • [35] DNA binding, cleavage and cytotoxicity studies of three mononuclear Cu(II) chloro-complexes containing N-S donor Schiff base ligands
    Parsekar, Sidhali U.
    Fernandes, Joseph
    Banerjee, Arnab
    Chouhan, Om Prakash
    Biswas, Sumit
    Singh, Manohar
    Mishra, Durga P.
    Kumar, Manjuri
    JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY, 2018, 23 (08): : 1331 - 1349
  • [36] Catecholase activity, DNA cleavage and cytotoxicity of six Zn(II) complexes synthesized from designed Mannich ligands: higher reactivity of mononuclear over dinuclear
    Ria Sanyal
    Sandeep Kumar Dash
    Sudhanshu Das
    Sourav Chattopadhyay
    Somenath Roy
    Debasis Das
    JBIC Journal of Biological Inorganic Chemistry, 2014, 19 : 1099 - 1111
  • [37] Catecholase activity, DNA cleavage and cytotoxicity of six Zn(II) complexes synthesized from designed Mannich ligands: higher reactivity of mononuclear over dinuclear
    Sanyal, Ria
    Dash, Sandeep Kumar
    Das, Sudhanshu
    Chattopadhyay, Sourav
    Roy, Somenath
    Das, Debasis
    JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY, 2014, 19 (07): : 1099 - 1111
  • [38] Mixed-ligand copper(II) Schiff base complexes: the role of the co-ligand in DNA binding, DNA cleavage, protein binding and cytotoxicity
    Lian, Wen-Jing
    Wang, Xin-Tian
    Xie, Cheng-Zhi
    Tian, He
    Song, Xue-Qing
    Pan, He-Ting
    Qiao, Xin
    Xu, Jing-Yuan
    DALTON TRANSACTIONS, 2016, 45 (22) : 9073 - 9087
  • [39] Syntheses of Zn(II) and Cu(II) Schiff base complexes using N,O donor Schiff base ligand: Crystal structure, DNA binding, DNA cleavage, docking and DFT study
    Ghorai, Pravat
    Saha, Rumpa
    Bhuiya, Sutanwi
    Das, Suman
    Brandao, Paula
    Ghosh, Dipanjan
    Bhaumik, Tanurima
    Bandyopadhyay, Parbati
    Chattopadhyay, Dhrubajyoti
    Saha, Amrita
    POLYHEDRON, 2018, 141 : 153 - 163
  • [40] DNA binding and cleavage study of ternary amino acid Schiff base Cu(II) complex at physiological conditions
    不详
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238