Library screening for synthetic agonists and antagonists of a Pseudomonas aeruginosa autoinducer

Chem Biol. 2003 Jun;10(6):563-71. doi: 10.1016/s1074-5521(03)00107-8.

Abstract

The autoinducer (AI) that initiates the quorum sensing (QS) signaling cascade in Pseudomonas aeruginosa is an acyl-homoserine lactone (acyl-HSL). We initiated a study of the requirements for binding of the AI to its protein effector LasR by synthesizing a library of analogs with the HSL moiety replaced with different amines and alcohols. We tested each compound for both agonist and antagonist activity using a QS-controlled reporter gene assay and found several new agonists and antagonists. A representative antagonist was further tested for its ability to inhibit virulence factors. This data progresses our understanding of the LasR-AI interaction toward the rational design of therapeutic inhibitors of QS.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • 4-Butyrolactone / pharmacology
  • Aminophenols / chemistry
  • Bacterial Proteins
  • Biofilms / drug effects
  • Biofilms / growth & development
  • DNA-Binding Proteins / chemistry
  • DNA-Binding Proteins / metabolism*
  • Drug Design
  • Gene Library*
  • Genes, Reporter / drug effects
  • Genetic Techniques
  • Homoserine / agonists
  • Homoserine / analogs & derivatives*
  • Homoserine / antagonists & inhibitors
  • Homoserine / chemical synthesis
  • Homoserine / genetics
  • Homoserine / metabolism*
  • Homoserine / pharmacology
  • Lactones / agonists
  • Lactones / antagonists & inhibitors
  • Lactones / metabolism*
  • Molecular Structure
  • Pseudomonas aeruginosa / metabolism
  • Pseudomonas aeruginosa / pathogenicity*
  • Quinolones / pharmacology
  • Signal Transduction / drug effects
  • Structure-Activity Relationship
  • Trans-Activators / chemistry
  • Trans-Activators / metabolism*
  • Virulence Factors / biosynthesis
  • Virulence Factors / genetics

Substances

  • 2-heptyl-3-hydroxy-4-quinolone
  • Aminophenols
  • Bacterial Proteins
  • DNA-Binding Proteins
  • Lactones
  • LasR protein, Pseudomonas aeruginosa
  • N-(3-oxododecanoyl)homoserine lactone
  • N-butyrylhomoserine lactone
  • Quinolones
  • Trans-Activators
  • Virulence Factors
  • Pseudomonas aeruginosa autoinducer
  • 2-aminophenol
  • Homoserine
  • 4-Butyrolactone