Inhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; a novel potent inhibitor of signalling

(S)-4,5-Dihydroxypentane-2,3-dione [(S)-DPD, (1)] is a precursor for , 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 () is reported. An intermediate in this route also enables a new...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2014-05, Vol.50 (39), p.5000-5002
Main Authors: Kadirvel, Manikandan, Fanimarvasti, Fariba, Forbes, Sarah, McBain, Andrew, Gardiner, John M, Brown, Gavin D, Freeman, Sally
Format: Article
Language:English
Subjects:
Bacterial Physiological Phenomena - drug effects
Biofilms - drug effects
Biofilms - growth & development
Luminescent Measurements
Molecular Structure
Pentanones - chemistry
Pentanones - pharmacology
Quorum Sensing - drug effects
Signal Transduction - drug effects
Vibrio - drug effects
Vibrio - physiology
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Summary:(S)-4,5-Dihydroxypentane-2,3-dione [(S)-DPD, (1)] is a precursor for , 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 () 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.
ISSN:1364-548X
DOI:10.1039/c3cc49678c