Coordination of an amino alcoholic Schiff base ligand toward the zinc(II) ion: spectral, structural, theoretical, and docking studies

J. Esmaeilzadeh*, Z. Mardani, K. Moeini, C. Carpenter-Warren, A.M.Z. Slawin, J.D. Woollins

*Corresponding author for this work

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Abstract

A new zinc(II) complex of 2-(((2-((2-hydroxyethyl)amino)ethyl)imino)methyl)phenol (L), [Zn(Lz)Br2] (1), is prepared and identified by elemental analysis, FTIR and 1H NMR spectroscopy, and single crystal X-ray diffraction. The X-ray structure analysis of 1 reveals a tetrahedrally coordinated zinc(II) complex containing the NO-donor amino alcoholic Schiff base ligand and two bromo ligands. After complexation, the ligand (L) converts to its zwitterionc form (Lz) of phenol → phenolate; amine → ammonium. In this structure, hydrogen bonds between amine and alcohol units form different types of hydrogen bond motifs, including R12(7),R22(7), R22(10), R44(24), R44(30), R66(38), and R66(44). In addition to the hydrogen bonds in this crystal network, there are π–π stacking interactions between the phenyl ring and the imine group. The ability of the ligand and its isostructural complexes [Zn(Lz)Br2] (1), [Zn(Lz)Cl2] (2), and [Zn(Lz)I2] (3) to interact with ten selected biomacromolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR, TS, Top II, and B-DNA) is investigated by docking studies. The results show that in some cases, the studied compound can interact with proteins and DNA better than doxorubicin. The charge distribution pattern of the ligand and complex 1 is studied by the NBO analysis.
Original languageEnglish
Pages (from-to)S8-S19
Number of pages12
JournalJournal of Structural Chemistry
Volume62
Issue numberSupplement issue 1
Early online date18 Feb 2022
DOIs
Publication statusPublished - 1 Dec 2022

Keywords

  • Amino alcohol
  • DFT
  • Docking study
  • Protein
  • Schiff base
  • Zinc

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