Antibacterial Small Molecules That Potently Inhibit Staphylococcus aureus Lipoteichoic Acid Biosynthesis

ChemMedChem. 2019 May 17;14(10):1000-1004. doi: 10.1002/cmdc.201900053. Epub 2019 Apr 30.

Abstract

The rise of antibiotic resistance, especially in Staphylococcus aureus, and the increasing death rate due to multiresistant bacteria have been well documented. The need for new chemical entities and/or the identification of novel targets for antibacterial drug development is high. Lipoteichoic acid (LTA), a membrane-attached anionic polymer, is important for the growth and virulence of many Gram-positive bacteria, and interest has been high in the discovery of LTA biosynthesis inhibitors. Thus far, only a handful of LTA biosynthesis inhibitors have been described with moderate (MIC=5.34 μg mL-1 ) to low (MIC=1024 μg mL-1 ) activities against S. aureus. Herein we describe the identification of novel compounds that potently inhibit LTA biosynthesis in S. aureus, displaying impressive antibacterial activities (MIC as low as 0.25 μg mL-1 ) against methicillin-resistant S. aureus (MRSA). Under similar in vitro assay conditions, these compounds are 4-fold more potent than vancomycin and 8-fold more potent than linezolid against MRSA.

Keywords: 1,3,4-oxadiazole; LTA biosynthesis inhibitors; MRSA; antibacterial activity; antibiotic resistance.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Dose-Response Relationship, Drug
  • Lipopolysaccharides / antagonists & inhibitors*
  • Lipopolysaccharides / biosynthesis
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Small Molecule Libraries / chemical synthesis
  • Small Molecule Libraries / chemistry
  • Small Molecule Libraries / pharmacology*
  • Staphylococcus aureus / drug effects*
  • Staphylococcus aureus / metabolism
  • Structure-Activity Relationship
  • Teichoic Acids / antagonists & inhibitors*
  • Teichoic Acids / biosynthesis

Substances

  • Anti-Bacterial Agents
  • Lipopolysaccharides
  • Small Molecule Libraries
  • Teichoic Acids
  • lipoteichoic acid