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Issue 47, 2015
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Synthesis and antibiotic activity of oxazolidinone–catechol conjugates against Pseudomonas aeruginosa

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Abstract

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.

Graphical abstract: Synthesis and antibiotic activity of oxazolidinone–catechol conjugates against Pseudomonas aeruginosa

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Submitted
06 Sep 2015
Accepted
22 Oct 2015
First published
22 Oct 2015

Org. Biomol. Chem., 2015,13, 11567-11579
Article type
Paper
Author version available

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

A. Paulen, V. Gasser, F. Hoegy, Q. Perraud, B. Pesset, I. J. Schalk and G. L. A. Mislin, Org. Biomol. Chem., 2015, 13, 11567
DOI: 10.1039/C5OB01859E

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