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
  • [41] Effect of structure and composition of nickel(II) complexes with salicylidene Schiff base ligands on their DNA/protein interaction and cytotoxicity
    Li, Peng
    Niu, Meiju
    Hong, Min
    Cheng, Shuang
    Dou, JianMin
    JOURNAL OF INORGANIC BIOCHEMISTRY, 2014, 137 : 101 - 108
  • [42] DNA binding, photoactivated DNA cleavage and cytotoxic activity of Cu(II) and Co(II) based Schiff-base azo photosensitizers
    Pradeepa, S. M.
    Naik, H. S. Bhojya
    Kumar, B. Vinay
    Priyadarsini, K. Indira
    Barik, Atanu
    Prabhakara, M. C.
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2015, 141 : 34 - 42
  • [43] Comparative DNA binding and DNA cleavage studies of a water soluble dinitrogen Schiff base ligand and its cobalt (II) complex
    Shahabadi, Nahid
    Kashanian, Soheila
    Darabi, Farivash
    JOURNAL OF BIOTECHNOLOGY, 2010, 150 : S185 - S185
  • [44] Synthesis, characterization, antimicrobial activity and DNA cleavage activity studies of Metal (II) complexes with a benzofuran Schiff's base
    Halli, M. B.
    Vijayalaxmi
    Patil, B.
    RESEARCH JOURNAL OF CHEMISTRY AND ENVIRONMENT, 2011, 15 (02): : 67 - 73
  • [45] DNA Binding and Anticancer Properties of New Pd(II)-Phosphorus Schiff Base Metal Complexes
    Demir, Burcu Saygideger
    Ince, Simay
    Yilmaz, Mustafa Kemal
    Sezan, Aycan
    Derinoz, Ezgi
    Taskin-Tok, Tugba
    Saygideger, Yasemin
    PHARMACEUTICS, 2022, 14 (11)
  • [46] Synthesis, characterization of Schiff base metal complexes with 1, 3 propanediamine as secondary chelates and their DNA binding, DNA cleavage, cytotoxicity, antioxidant and activities
    Pichandi, Mahadevi
    Shanmugam, Sumathi
    JOURNAL OF MOLECULAR STRUCTURE, 2024, 1307
  • [47] Synthesis, Spectral Characterization, DNA/ Protein Binding, DNA Cleavage, Cytotoxicity, Antioxidative and Molecular Docking Studies of Cu(II)Complexes Containing Schiff Base-bpy/Phen Ligands
    Berelli Anupama
    Airva Aruna
    Vijjulatha Manga
    Sreekanth Sivan
    Madamsetty Vijay Sagar
    Ravula Chandrashekar
    Journal of Fluorescence, 2017, 27 : 953 - 965
  • [48] Synthesis, Spectral Characterization, DNA/ Protein Binding, DNA Cleavage, Cytotoxicity, Antioxidative and Molecular Docking Studies of Cu(II)Complexes Containing Schiff Base-bpy/Phen Ligands
    Anupama, Berelli
    Aruna, Airva
    Manga, Vijjulatha
    Sivan, Sreekanth
    Sagar, Madamsetty Vijay
    Chandrashekar, Ravula
    JOURNAL OF FLUORESCENCE, 2017, 27 (03) : 953 - 965
  • [49] Synthesis and Biological Activity Evaluation of Some Binuclear Metal Complexes of Cu(II) and Zn(II) with Tridentate Schiff Base Ligands
    Mobinikhaledi, Akbar
    Zendehdel, Mojgan
    Safari, Parvin
    Hamta, Ahmad
    Shariatzadeh, S. Mehdi
    SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2012, 42 (02) : 165 - 170
  • [50] New tailored substituted benzothiazole Schiff base Cu(II)/Zn(II) antitumor drug entities: effect of substituents on DNA binding profile, antimicrobial and cytotoxic activity
    Zehra, Siffeen
    Khan, Mohammad Shavez
    Ahmad, Iqbal
    Arjmand, Farukh
    JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 2019, 37 (07): : 1863 - 1879