Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 20, Issue 1, Pages 249-256Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2011.11.007
Keywords
AI-2; DPD; DPD analogs; DPD agonist; Quorum sensing
Funding
- Programa Operacional Ciencia e Inovacao (POCI)
- Fundacao para a Ciencia e a Tecnologia (FCT)
- FCT [PTDC/QUI-BIQ/113880/2009, PEst-OE/EQB/LA0004/2011]
- ITQB
- Fundação para a Ciência e a Tecnologia [PTDC/QUI-BIQ/113880/2009] Funding Source: FCT
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Bacteria coordinate population-dependent behaviors such as virulence by intra-and inter-species communication (quorum sensing). Autoinducer-2 (AI-2) regulates inter-species quorum sensing. AI-2 derives from the spontaneous cyclisation of linear (S)-4,5-dihydroxypentanedione (DPD) into two isomeric forms in dynamic equilibrium. Different species of bacteria have different classes of AI-2 receptors (LsrB and LuxP) which bind to different cyclic forms. In the present work, DPD analogs with a new stereocenter at C-5 (4,5-dihydroxyhexanediones (DHDs)) have been synthesized and their biological activity tested in two bacteria. (4S, 5R)-DHD is a synergistic agonist in Escherichia coli (which contains the LsrB receptor), while it is an agonist in Vibrio harveyi (LuxP), displaying the strongest agonistic activity reported so far (EC50 = 0.65 mu M) in this organism. Thus, modification at C-5 opens the way to novel methods to manipulate quorum sensing as a method for controlling bacteria. (C) 2011 Elsevier Ltd. All rights reserved.
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