Oxidatively Locked [Co₂L₃]6+ Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole "Click" Ligands: Synthesis, Stability, and Antimicrobial Studies

Molecules. 2016 Nov 16;21(11):1548. doi: 10.3390/molecules21111548.

Abstract

A small family of [Co₂(Lpytrz)₃]6+ cylinders was synthesised from bis(bidentate) 2-pyridyl-1,2,3-triazole "click" ligands (Lpytrz) through an "assembly-followed-by-oxidation" method. The cylinders were characterised using ¹H, 13C, and DOSY NMR, IR, and UV-Vis spectroscopies, along with electrospray ionisation mass spectrometry (ESMS). Stability studies were conducted in dimethyl sulfoxide (DMSO) and D₂O. In contrast to similar, previously studied, [Fe₂(Lpytrz)₃]4+ helicates the more kinetically inert [Co₂(Lpytrz)₃]6+ systems proved stable (over a period of days) when exposed to DMSO and were even more stable in D₂O. The triply stranded [Co₂(Lpytrz)₃]6+ systems and the corresponding "free" ligands were tested for antimicrobial activity in vitro against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) microorganisms. Agar-based disk diffusion and Mueller-Hinton broth micro-dilution assays showed that the [Co₂(Lpytrz)₃]6+ cylinders were not active against either strain of bacteria. It is presumed that a high charge of the [Co₂(Lpytrz)₃]6+ cylinders is preventing them from crossing the bacterial cell membranes, rendering the compounds biologically inactive.

Keywords: antimicrobial agents; cobalt(III); cylinders; metallosupramolecular.

MeSH terms

  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology*
  • Bacteria / drug effects
  • Click Chemistry*
  • Cobalt / chemistry*
  • Drug Stability
  • Ligands
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Proton Magnetic Resonance Spectroscopy
  • Triazoles / chemistry*

Substances

  • Anti-Infective Agents
  • Ligands
  • Organometallic Compounds
  • Triazoles
  • Cobalt