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

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

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Equipe Transport Membranaire Bactérien, Biotechnologie et Signalisation Cellulaire, UMR7242 Université de Strasbourg-CNRS, Pole API, 300 boulevard Sébastien Brant, CS10413, 67412 Illkirch Cedex, France.


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.

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