Issue 44, 2021

Fluorinated quorum sensing inhibitors: enhancement of potency through conformational control

Abstract

The bacterial quorum sensing (QS) system is a target for non-lethal antibacterial agents that do not encourage the development of resistance. QS inhibitors commonly contain a polar “head” moiety and a lipidic “tail” moiety. In this work, we synthesised novel QS inhibitor candidates in which the lipidic “tail” is decorated with stereospecifically positioned fluorine atoms. The presence of fluorine is shown to bias the molecules into distinctive conformations that are pre-organised for binding to the QS receptor. This translates into significant increases in QS inhibitory potency.

Graphical abstract: Fluorinated quorum sensing inhibitors: enhancement of potency through conformational control

Supplementary files

Article information

Article type
Paper
Submitted
22 Aug 2021
Accepted
20 Oct 2021
First published
21 Oct 2021

Org. Biomol. Chem., 2021,19, 9629-9636

Fluorinated quorum sensing inhibitors: enhancement of potency through conformational control

Y. Lizarme-Salas, T. T. Yu, C. de Bruin-Dickason, N. Kumar and L. Hunter, Org. Biomol. Chem., 2021, 19, 9629 DOI: 10.1039/D1OB01649K

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