Allicin-inspired pyridyl disulfides as antimicrobial agents for multidrug-resistant Staphylococcus aureus

Eur J Med Chem. 2018 Jan 1:143:1185-1195. doi: 10.1016/j.ejmech.2017.10.018. Epub 2017 Oct 12.

Abstract

A chemical library comprised of nineteen synthesized pyridyl disulfides that emulate the chemical reactivity of allicin (garlic) was evaluated for antimicrobial activity against a panel of pathogenic bacteria. Gram-positive species including vancomycin-intermediate and vancomycin-resistant Staphylococcus aureus (VISA, VRSA) demonstrated the highest level of susceptibility toward analogs with S-alkyl chains of 7-9 carbons in length. Further biological studies revealed that the disulfides display synergy with vancomycin against VRSA, cause dispersal of S. aureus biofilms, exhibit low cytotoxicity, and decelerate S. aureus metabolism. In final analysis, pyridyl disulfides represent a novel class of mechanism-based antibacterial agents that have a potential application as antibiotic adjuvants in combination therapy of S. aureus infections with reduced vancomycin susceptibility.

Keywords: Allicin; Antibiotics; Disulfides; MRSA; Narrow-spectrum; Staphylococcus aureus; VISA; VRSA.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Biofilms / drug effects
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Disulfides / chemistry
  • Disulfides / pharmacology*
  • Dose-Response Relationship, Drug
  • Humans
  • Methicillin-Resistant Staphylococcus aureus / drug effects*
  • Methicillin-Resistant Staphylococcus aureus / growth & development
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Pyridines / chemistry
  • Pyridines / pharmacology*
  • Structure-Activity Relationship
  • Sulfinic Acids / chemistry
  • Sulfinic Acids / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Disulfides
  • Pyridines
  • Sulfinic Acids
  • allicin