[Fe₂L₃]⁴⁺ cylinders derived from bis(bidentate) 2-pyridyl-1,2,3-triazole "click" ligands: synthesis, structures and exploration of biological activity

Molecules. 2013 May 29;18(6):6383-407. doi: 10.3390/molecules18066383.

Abstract

A series of metallosupramolecular [Fe₂L₃](BF₄)₄ "click" cylinders have been synthesized in excellent yields (90%-95%) from [Fe(H₂O)₆](BF₄)₂ and bis(bidentate) pyridyl-1,2,3-triazole ligands. All complexes were characterized by elemental analysis, IR, UV-vis, ¹H-, ¹³C- and DOSY-NMR spectroscopies and, in four cases, the structures confirmed by X-ray crystallography. Molecular modeling indicated that some of these "click" complexes were of similar size and shape to related biologically active pyridylimine-based iron(II) helicates and suggested that the "click" complexes may bind both duplex and triplex DNA. Cell-based agarose diffusion assays showed that the metallosupramolecular [Fe₂L₃](BF₄)₄ "click" cylinders display no antifungal activity against S. cerevisiae. This observed lack of antifungal activity appears to be due to the poor stability of the "click" complexes in DMSO and biological media.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Click Chemistry*
  • DNA / chemistry
  • Disk Diffusion Antimicrobial Tests
  • Ferrous Compounds / chemical synthesis
  • Ferrous Compounds / chemistry*
  • Ferrous Compounds / pharmacology
  • Models, Molecular
  • Molecular Docking Simulation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*
  • Pyridines / pharmacology
  • Triazoles / chemical synthesis
  • Triazoles / chemistry*
  • Triazoles / pharmacology

Substances

  • Antifungal Agents
  • Ferrous Compounds
  • Pyridines
  • Triazoles
  • triplex DNA
  • DNA
  • pyridine