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

Research output: Contribution to journalArticlepeer-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 languageEnglish
Pages (from-to)5000-5002
Number of pages3
JournalChemical Communications
Volume50
Issue number39
Early online date7 Mar 2014
DOIs
Publication statusPublished - 21 May 2014

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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