Synthesis, crystal structure and biological evaluation of spectroscopic characterization of Ni(II) and Co(II) complexes with N-salicyloil-N'-maleoil-hydrazine as anticholinergic and antidiabetic agents

J Biochem Mol Toxicol. 2018 Sep;32(9):e22197. doi: 10.1002/jbt.22197. Epub 2018 Jul 25.

Abstract

[Ni(C11 H9 N2 O5 )2 (H2 O)2 ]•3(C3 H7 NO) (1) and [Co(C11 H9 N2 O5 )2 (H2 O)2 ]•3(C3 H7 NO) (2) are synthesized and characterized by elemental analysis, FT-IR spectra, magnetic susceptibility, and thermal analysis. In addition, the crystal structure of Ni(II) complex is presented. Both complexes show distorted octahedral geometry. In 1 and 2, metal ions are coordinated by two oxygen atoms of salicylic residue and two nitrogen atoms of maleic amide residue from two ligands, and two oxygen atoms from two water molecules. In this paper, both compounds showed excellent inhibitory effects against human carbonic anhydrase (hCA) isoforms I, and II, α-glycosidase, acetylcholinesterase (AChE), and butyrylcholinesterase (BChE). Compounds 1 and 2 had Ki values of 18.36 ± 4.38 and 26.61 ± 7.54 nM against hCA I and 13.81 ± 3.02 and 29.56 ± 6.52 nM against hCA II, respectively. On the other hand, their Ki values were found to be 487.45 ± 54.18 and 453.81 ± 118.61 nM against AChE and 199.21 ± 50.35 and 409.41 ± 6.86 nM against BChE, respectively.

Keywords: N-salicyloil-N’-maleoil-hydrazine; crystal structure; enzyme inhibition; magnetic properties; synthesis.

Publication types

  • Comparative Study

MeSH terms

  • Acetylcholinesterase / chemistry
  • Acetylcholinesterase / metabolism
  • Animals
  • Butyrylcholinesterase / chemistry
  • Butyrylcholinesterase / metabolism
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Carbonic Anhydrase I / antagonists & inhibitors
  • Carbonic Anhydrase I / chemistry
  • Carbonic Anhydrase I / metabolism
  • Carbonic Anhydrase II / antagonists & inhibitors
  • Carbonic Anhydrase II / metabolism
  • Cholinergic Antagonists / chemical synthesis
  • Cholinergic Antagonists / chemistry
  • Cholinergic Antagonists / pharmacology*
  • Cholinesterase Inhibitors / chemical synthesis
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology
  • Cobalt / chemistry
  • Cobalt / pharmacology*
  • Coordination Complexes / chemistry
  • Coordination Complexes / pharmacology*
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Glycoside Hydrolases / antagonists & inhibitors
  • Glycoside Hydrolases / metabolism
  • Humans
  • Hydrazines / chemical synthesis
  • Hydrazines / chemistry
  • Hydrazines / pharmacology*
  • Hypoglycemic Agents / chemical synthesis
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / pharmacology*
  • Magnetic Phenomena
  • Molecular Structure
  • Nickel / chemistry
  • Nickel / pharmacology*
  • Proton Magnetic Resonance Spectroscopy
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Cholinergic Antagonists
  • Cholinesterase Inhibitors
  • Coordination Complexes
  • Enzyme Inhibitors
  • Hydrazines
  • Hypoglycemic Agents
  • N-salicyloil-N'-maleoil-hydrazine
  • Cobalt
  • Nickel
  • Acetylcholinesterase
  • Butyrylcholinesterase
  • Glycoside Hydrolases
  • Carbonic Anhydrase I
  • Carbonic Anhydrase II
  • CA1 carbonic anhydrase, human