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Synthesis of conjugates between oxazolidinone antibiotics and a pyochelin analogue

Aurélie Paulen1, Françoise Hoegy1, Béatrice Roche1

  • 1CNRS Equipe Transport Membranaire Bactérien, Biotechnologie et Signalisation Cellulaire, UMR7242, Pole API, 300 boulevard Sébastien Brant, CS10413, 67412 Illkirch Cedex, France; University of Strasbourg, Ecole Supérieure de Biotechnologie de Strasbourg (ESBS), F-67413 Illkirch Cedex, France.

Bioorganic & Medicinal Chemistry Letters
|September 27, 2017
PubMed

Insights

Researchers developed novel pyochelin-oxazolidinone conjugates to combat Pseudomonas aeruginosa infections. These conjugates enhance oxazolidinone uptake, potentially overcoming antibiotic resistance in this Gram-negative pathogen.

Area of Science:

  • Microbiology and Infectious Diseases
  • Medicinal Chemistry
  • Bacterial Pathogenesis

Background:

  • Pseudomonas aeruginosa is a Gram-negative bacterium causing severe infections and exhibiting resistance to numerous antibiotics.
  • Oxazolidinone antibiotics are effective against Gram-positive bacteria but not P. aeruginosa due to limited uptake.
  • Pyochelin, a siderophore, facilitates iron transport into P. aeruginosa, presenting a potential delivery mechanism for antibiotics.

Purpose of the Study:

  • To synthesize novel pyochelin-oxazolidinone conjugates as a strategy to enhance oxazolidinone delivery into P. aeruginosa.
  • To explore the potential of pyochelin as a Trojan Horse vector for overcoming antibiotic resistance in P. aeruginosa.

Main Methods:

  • Synthesis of novel conjugates by linking amine-functionalized pyochelin with carboxylate-functionalized oxazolidinones.
  • Utilized a regioselective peptide coupling reaction for conjugate formation.

Main Results:

  • Successfully synthesized novel pyochelin-oxazolidinone conjugates.
  • The synthesis demonstrated unexpected regioselectivity in the peptide coupling reaction.

Conclusions:

  • Pyochelin-oxazolidinone conjugates represent a promising approach to enhance oxazolidinone efficacy against P. aeruginosa.
  • This strategy could offer a new avenue for combating antibiotic-resistant Gram-negative bacterial infections.
Keywords:
LinezolidOxazolidinone antibioticPyochelinSiderophoreTrojan Horse strategy

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