Discovery and optimization of thiazole-based quorum sensing inhibitors as potent blockers of Pseudomonas aeruginosa pathogenicity

Eur J Med Chem. 2024 Oct 5:276:116685. doi: 10.1016/j.ejmech.2024.116685. Epub 2024 Jul 16.

Abstract

Pseudomonas aeruginosa causes life-threatening infections especially in hospitalized patients and shows an increasing resistance to established antibiotics. A process known as quorum sensing (QS) enables the pathogen to collectively adapt to various environmental conditions. Disrupting this cell-to-cell communication machinery by small-molecular entities leads to a blockade of bacterial pathogenicity. We aim to devise QS inhibitors acting on the PA-specific PQS QS system via the signal-molecule receptor and transcriptional regulator PqsR (MvfR). In this manuscript, we describe the further optimization of PqsR inverse agonists by broadening the structural space of a previously described triazole-bearing lead compound and arriving at highly potent thiazole derivatives with activities against P. aeruginosa virulence factor pyocyanin in the nanomolar range. All new derivatives were profiled regarding biological activity as well as in vitro ADMET parameters. Additionally, we assessed safety-pharmacology characteristics of the two most promising compounds both bearing a 3-chloro-4-isopropoxyphenyl motive. Demonstrating an overall favorable profile, our new PqsR inverse agonists represent a valuable addition as optimized lead compounds, enabling preclinical development of P. aeruginosa-specific pathoblockers.

MeSH terms

  • Animals
  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Bacterial Proteins / antagonists & inhibitors
  • Bacterial Proteins / metabolism
  • Dose-Response Relationship, Drug
  • Drug Discovery
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Pseudomonas aeruginosa* / drug effects
  • Quorum Sensing* / drug effects
  • Structure-Activity Relationship
  • Thiazoles* / chemical synthesis
  • Thiazoles* / chemistry
  • Thiazoles* / pharmacology

Substances

  • Thiazoles
  • Anti-Bacterial Agents
  • Bacterial Proteins