Synthesis of New Naphthyl Aceto Hydrazone-Based Metal Complexes: Micellar Interactions, DNA Binding, Antimicrobial, and Cancer Inhibition Studies

Molecules. 2021 Feb 17;26(4):1044. doi: 10.3390/molecules26041044.

Abstract

In the present study, naphthyl acetohydrazide (HL) ligand was prepared and used for the synthesis of new six amorphous transition metal (Co(II), Ni(II), Cu(II), Zn(II), Pb(II), Cd(II)) complexes. All the compounds were characterized by elemental analysis, UV-vis, FT-IR, 1H- and 13C-NMR, and Matrix-Assisted Laser Desorption Ionization (MALDI). The solubilization study was carried out by estimating the interaction between the metal complexes with surfactants viz. sodium stearate (SS) and Cetyltrimethylammonium bromide (CTAB). UV-Visible spectroscopy was employed to determine partitioning and binding parameters, whereas electrical conductivity measurements were employed to estimate critical micellar concentration (CMC), the extent of dissociation, and free energy of micellization. The CT-DNA interaction of synthesized compounds with DNA represents the major groove binding. The synthesized ligand and metal complexes were also tested against bacterial and fungal strains and it has been observed that Cu(II) complex is active against all the strains except Candida albicans, while Cd(II) complex is active against all bacterial and fungal strains except Pseudomonas. Among all compounds, only the Pd(II) complex shows reasonable activity against cervical cancer HeLa cell lines, representing 97% inhibition.

Keywords: DNA interaction; MALDI; anti-cancer activity; hydrazones; micellar interaction; microbial inhibition.

MeSH terms

  • Anti-Infective Agents / pharmacology*
  • Bacteria / drug effects
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Cell Survival / drug effects
  • Coordination Complexes / chemical synthesis*
  • DNA / metabolism*
  • Electric Conductivity
  • HeLa Cells
  • Humans
  • Hydrazones / chemical synthesis*
  • Hydrazones / chemistry
  • Hydrazones / pharmacology*
  • Ligands
  • Metals / chemistry*
  • Micelles*
  • Microbial Sensitivity Tests
  • Neoplasms / pathology*
  • Proton Magnetic Resonance Spectroscopy
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Spectrophotometry, Ultraviolet
  • Spectroscopy, Fourier Transform Infrared
  • Surface-Active Agents / chemistry

Substances

  • Anti-Infective Agents
  • Coordination Complexes
  • Hydrazones
  • Ligands
  • Metals
  • Micelles
  • Surface-Active Agents
  • DNA