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Synthesis of conjugates between oxazolidinone antibiotics and a pyochelin analogue.

Abstract：

:Pseudomonas aeruginosa is a Gram-negative pathogenic bacterium responsible for severe infections, and it is naturally resistant to many clinically approved antibiotic families. Oxazolidinone antibiotics are active against many Gram-positive bacteria, but are inactive against P. aeruginosa. Increasing the uptake of oxazolidinones through the bacterial envelope could lead to an increased antibiotic effect. Pyochelin is a siderophore of P. aeruginosa which delivers external iron to the bacterial cytoplasm and is a potential vector for the development of Trojan Horse oxazolidinone conjugates. Novel pyochelin-oxazolidinone conjugates were synthesized using an unexpectedly regioselective peptide coupling between an amine functionalized pyochelin and oxazolidinones functionalized with a terminal carboxylate.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Paulen A,Hoegy F,Roche B,Schalk IJ,Mislin GLA

doi

10.1016/j.bmcl.2017.09.039

subject

Has Abstract

pub_date

2017-11-01 00:00:00

pages

4867-4870

issue

21

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(17)30935-6

journal_volume

27

pub_type

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