TY - JOUR
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. © 2014 The Partner Organisations.
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. © 2014 The Partner Organisations.
U2 - 10.1039/c3cc49678c
DO - 10.1039/c3cc49678c
M3 - Article
SN - 1359-7345
VL - 50
SP - 5000
EP - 5002
JO - Chemical Communications
JF - Chemical Communications
IS - 39
ER -