Synthesis, Characterization, Antimicrobial and Antiproliferative Activity Evaluation of Cu(II), Co(II), Zn(II), Ni(II) and Pt(II) Complexes with Isoniazid-Derived Compound

Molecules. 2017 Apr 19;22(4):650. doi: 10.3390/molecules22040650.

Abstract

Hydrazone complexes of Cu(II), Co(II), Zn(II), Ni(II) and Pt(II) with N-isonicotinoyl-N'-(3-metoxy-2 hydroxybenzaldehyde)-hydrazone (HL) were synthesized and characterized by different physico-chemical techniques including elemental and thermal analysis, magnetic susceptibility measurements, molar electric conductivity, as well as IR (infrared), ¹H-NMR and 13C-NMR (hydrogen and carbon nuclear magnetic resonance, UV-Vis (ultraviolet-visible), FAB (fast atom bombardment), EPR (electron paramagnetic resonance), and mass spectroscopies. The crystal structure of ligand was determined by single crystal X-ray diffraction studies. Spectral data showed that hydrazone behaves as an ONO tridentate ligand through the azomethine nitrogen, phenolate and keto oxygen atoms. For the copper(II) complexes, metal-ligand bonding parameters were evaluated from the EPR spectra. These parameters indicate the presence of in-plane π bonding. In addition, the f values of complexes 1-4 indicate small distortion from planarity. The effect of these complexes on proliferation of human breast cancer (MCF-7 and SKBR-3), human melanoma (A375), lung adenocarcinoma cells (NCI-H1573) and their antibacterial activity against Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus and Candida albicans strains were studied and compared with those of free ligand. The ligand and complexes 1-3 showed significant antimicrobial activity against the Gram-positive bacteria Staphylococcus aureus and Candida albicans in comparison to the control drugs. The complexes 2-4 could be potential antitumor agents, leading to a significant improvement of the cytotoxic activity when compared with HL.

Keywords: antimicrobial activity; cobalt(II); copper(II); human breast SKBR-3 and MCF-7; human melanoma A375; lung adenocarcinoma cell NCI-H1573; nickel(II) and platinum(II) complexes; zinc(II).

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / pharmacology*
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology*
  • Bacteria / drug effects
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Cobalt / chemistry
  • Copper / chemistry
  • Fungi / drug effects
  • Humans
  • Isoniazid / analogs & derivatives
  • Isoniazid / chemical synthesis*
  • Isoniazid / pharmacology*
  • Metals / chemistry*
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Nickel / chemistry
  • Platinum / chemistry
  • Solubility
  • Spectrum Analysis / methods
  • Zinc / chemistry

Substances

  • Anti-Infective Agents
  • Antineoplastic Agents
  • Metals
  • Cobalt
  • Platinum
  • Copper
  • Nickel
  • Zinc
  • Isoniazid