Synthesis and biological properties of thiazole-analogues of pyochelin, a siderophore of Pseudomonas aeruginosa

Bioorg Med Chem Lett. 2014 Jan 1;24(1):132-5. doi: 10.1016/j.bmcl.2013.11.054. Epub 2013 Dec 4.

Abstract

Pyochelin is a siderophore common to all strains of Pseudomonas aeruginosa utilized by this Gram-negative bacterium to acquire iron(III). FptA is the outer membrane transporter responsible of ferric-pyochelin uptake in P. aeruginosa. We describe in this Letter the synthesis and the biological properties ((55)Fe uptake, binding to FptA) of several thiazole analogues of pyochelin. Among them we report in this Letter the two first pyochelin analogues able to bind FptA without promoting any iron uptake in P. aeruginosa.

Keywords: FptA; Outer membrane transporter; Pseudomonas aeruginosa; Pyochelin; Siderophore.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacterial Outer Membrane Proteins / chemistry*
  • Bacterial Outer Membrane Proteins / metabolism
  • Binding Sites
  • Iron / chemistry
  • Iron / metabolism
  • Molecular Structure
  • Phenols / chemical synthesis
  • Phenols / chemistry*
  • Phenols / metabolism
  • Pseudomonas aeruginosa / chemistry*
  • Receptors, Cell Surface / chemistry*
  • Receptors, Cell Surface / metabolism
  • Siderophores / chemical synthesis*
  • Siderophores / chemistry
  • Siderophores / metabolism
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry*
  • Thiazoles / metabolism

Substances

  • Bacterial Outer Membrane Proteins
  • FPTA protein, Pseudomonas
  • Phenols
  • Receptors, Cell Surface
  • Siderophores
  • Thiazoles
  • pyochelin
  • Iron