Xylose Incorporated in Unsymmetrical Gold(I) N-Heterocyclic Carbene Complexes: Synthesis, Characterization and Antibacterial Activity

ChemMedChem. 2024 Nov 18;19(22):e202400245. doi: 10.1002/cmdc.202400245. Epub 2024 Sep 24.

Abstract

A series of Au(I) complexes containing unsymmetrical N-heterocyclic carbene (imidazolylidene and benzimidazolylidene) functionalized with a xyloside group and an alkyl moiety (methyl and mesityl) was prepared using efficient procedures from D-xylose. Their characterization was carried out in solution by multinuclear NMR, HR-MS spectrometry and cyclic voltammetry, as well as in the solid state by means of single crystal X-ray diffraction analysis for two of them. Evaluation of their ability to inhibit bacterial growth showed a preference for a Gram-positive strain, Staphylococcus aureus, over a Gram-negative strain, Pseudomonas aeruginosa.

Keywords: Antibacterial; Complexes; Gold; N-heterocyclic carbene; Xylose.

MeSH terms

  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Coordination Complexes / chemical synthesis
  • Coordination Complexes / chemistry
  • Coordination Complexes / pharmacology
  • Crystallography, X-Ray
  • Gold* / chemistry
  • Gold* / pharmacology
  • Heterocyclic Compounds* / chemical synthesis
  • Heterocyclic Compounds* / chemistry
  • Heterocyclic Compounds* / pharmacology
  • Methane* / analogs & derivatives
  • Methane* / chemistry
  • Methane* / pharmacology
  • Microbial Sensitivity Tests*
  • Models, Molecular
  • Molecular Structure
  • Pseudomonas aeruginosa* / drug effects
  • Staphylococcus aureus* / drug effects
  • Structure-Activity Relationship
  • Xylose* / chemistry
  • Xylose* / pharmacology

Substances

  • Anti-Bacterial Agents
  • Methane
  • carbene
  • Xylose
  • Gold
  • Heterocyclic Compounds
  • Coordination Complexes