Fluorinated quorum sensing inhibitors: enhancement of potency through conformational control
- 21 October 2021
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 19 (44), 9629-9636
- https://doi.org/10.1039/d1ob01649k
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.Funding Information
- University of New South Wales
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