Inhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; a novel potent inhibitor of AI-2 signallingElectronic supplementary information (ESI) available: Experimental details including synthesis, NMR spectra, Mass and GC chromatogram and microbiological methods. See DOI: 10.1039/c3cc49678c

( S )-4,5-Dihydroxypentane-2,3-dione [( S )-DPD, ( 1 )] is a precursor for AI-2 , a quorum sensing signalling molecule for inter- and intra-species bacterial communication. The synthesis of its fluoro-analogue, 4-fluoro-5-hydroxypentane-2,3-dione ( 2 ) is reported. An intermediate in this route also...

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Main Authors: Kadirvel, Manikandan, Fanimarvasti, Fariba, Forbes, Sarah, McBain, Andrew, Gardiner, John M, Brown, Gavin D, Freeman, Sally
Format: Article
Language:English
Online Access:Get full text
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Summary:( S )-4,5-Dihydroxypentane-2,3-dione [( S )-DPD, ( 1 )] is a precursor for AI-2 , a quorum sensing signalling molecule for inter- and intra-species bacterial communication. The synthesis of its fluoro-analogue, 4-fluoro-5-hydroxypentane-2,3-dione ( 2 ) is reported. An intermediate in this route also enables a new, shorter synthesis of the native ( S )-DPD. 4-Fluoro-DPD ( 2 ) completely inhibited bioluminescence and bacterial growth of Vibrio harveyi BB170 strain at 12.5 μM and 100 μM, respectively. (±)4-Fluoro-DPD completely inhibited bioluminescence and bacterial growth of Vibrio harveyi BB170 strain by disruption of quorum sensing cascade.
ISSN:1359-7345
1364-548X
DOI:10.1039/c3cc49678c