Inhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; a novel potent inhibitor of AI-2 signalling

Manikandan Kadirvel; Fariba Fanimarvasti; Sarah Forbes; Andrew McBain; John M. Gardiner; Gavin D. Brown; Sally Freeman

doi:10.1039/c3cc49678c

Inhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; a novel potent inhibitor of AI-2 signalling

Manikandan Kadirvel
, Fariba Fanimarvasti
, Sarah Forbes
, Andrew McBain
, John M. Gardiner
, Gavin D. Brown
, Sally Freeman^*

^*Corresponding author for this work

Chemical Engineering

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

Abstract

(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.

Original language	English
Pages (from-to)	5000-5002
Number of pages	3
Journal	Chemical Communications
Volume	50
Issue number	39
Early online date	7 Mar 2014
DOIs	https://doi.org/10.1039/c3cc49678c
Publication status	Published - 21 May 2014

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "Inhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; a novel potent inhibitor of AI-2 signalling",

abstract = "(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.",

author = "Manikandan Kadirvel and Fariba Fanimarvasti and Sarah Forbes and Andrew McBain and Gardiner, \{John M.\} and Brown, \{Gavin D.\} and Sally Freeman",

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doi = "10.1039/c3cc49678c",

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journal = "Chemical Communications",

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T1 - Inhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; a novel potent inhibitor of AI-2 signalling

AU - Kadirvel, Manikandan

AU - Fanimarvasti, Fariba

AU - Forbes, Sarah

AU - McBain, Andrew

AU - Gardiner, John M.

AU - Brown, Gavin D.

AU - Freeman, Sally

PY - 2014/5/21

Y1 - 2014/5/21

N2 - (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.

AB - (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.

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DO - 10.1039/c3cc49678c

M3 - Article

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AN - SCOPUS:84898991993

SN - 1359-7345

VL - 50

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EP - 5002

JO - Chemical Communications

JF - Chemical Communications

IS - 39

ER -

Inhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; a novel potent inhibitor of AI-2 signalling

Abstract

ASJC Scopus subject areas

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