Synthesis and antibiotic activity of oxazolidinone-catechol conjugates against Pseudomonas aeruginosa

Org Biomol Chem. 2015 Dec 21;13(47):11567-79. doi: 10.1039/c5ob01859e.


Pseudomonas aeruginosa is a Gram-negative pathogenic bacterium responsible for severe infections in which resistance to most of the approved families of antibiotics is increasing. Oxazolidinone antibiotics are active against many Gram-positive bacteria, but are only weakly active against Gram-negative pathogens. We describe the synthesis of conjugates between a catechol moiety and oxazolidinone antibiotics. These conjugates were significantly more active against P. aeruginosa (218-1024 μM) than linezolid (MIC > 1024 μM), the reference molecule from the oxazolidinone family. Antibiotic activity was slightly higher in medium depleted of iron, suggesting the involvement of a bacterial iron uptake system in this biological activity. The bacterial iron uptake pathway involved in the transport is still to be addressed, but the present data excluded a contribution of the enterobactin transporter PfeA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Catechols / chemical synthesis
  • Catechols / chemistry*
  • Catechols / pharmacology*
  • Humans
  • Microbial Sensitivity Tests
  • Oxazolidinones / chemical synthesis
  • Oxazolidinones / chemistry*
  • Oxazolidinones / pharmacology*
  • Pseudomonas Infections / drug therapy
  • Pseudomonas aeruginosa / drug effects*


  • Anti-Bacterial Agents
  • Catechols
  • Oxazolidinones
  • catechol