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Structure-Aided Design of a LuxR-Type Quorum Sensing SuFEx-Based Potential Inhibitor: Covalent or Competitive

Laurent Soulère1, Sylvie Reverchon2, Jessica Baude2

  • 1INSA LYON, CPE Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Universite de Lyon 1, CNRS, UMR 5246, Bâtiment Lederer, 1 rue Victor Grignard, F-69622 Villeurbanne, France.

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New fluorosulfonyl-benzoyl acylhomoserine lactone derivatives show promise as competitive quorum sensing (QS) inhibitors. These compounds effectively block bacterial communication, offering potential antimicrobial strategies.

Keywords:
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Area of Science:

  • Medicinal Chemistry
  • Molecular Biology
  • Biochemistry

Background:

  • Quorum sensing (QS) is a cell-to-cell communication mechanism crucial for bacterial virulence.
  • LuxR-type receptors regulate QS systems, making them attractive targets for antimicrobial drug development.
  • Acylhomoserine lactone (AHL) analogs are commonly used as QS inhibitors.

Purpose of the Study:

  • To design, synthesize, and evaluate novel N-benzoyl-l-homoserine lactone derivatives as QS inhibitors.
  • To investigate the mechanism of action of these novel compounds.
  • To assess the potential of sulfonyl substituents in enhancing QS inhibition.

Main Methods:

  • Synthesis of N-benzoyl-l-homoserine lactone derivatives with meta-fluorosulfonyl or meta-methylsulfonyl groups.
  • Molecular docking simulations with LuxR-type receptors.
  • In vitro biological evaluation of inhibitory activity (IC50 determination).
  • Kinetic studies using 19F NMR and LC/MS analysis to elucidate the mechanism of action.

Main Results:

  • The meta-fluorosulfonyl derivative exhibited significant QS inhibitory activity with an IC50 of 15 ± 2 µM.
  • The meta-methylsulfonyl derivative showed weak inhibitory effects.
  • Stability of the fluorosulfonyl derivative was confirmed.
  • Experimental evidence strongly suggests a competitive inhibition mechanism.

Conclusions:

  • N-benzoyl-l-homoserine lactone derivatives with a meta-fluorosulfonyl group are effective competitive inhibitors of LuxR-regulated quorum sensing.
  • The sulfonyl substituent plays a key role in the binding interactions within the receptor's active site.
  • These findings highlight the potential of fluorosulfonyl-containing AHL analogs as novel antimicrobial agents targeting bacterial communication.