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Title: Synthesis and biological evaluation of homoserine lactone derived ureas as antagonists of bacterial quorum sensing
Authors: Frezza, Marine
Castang, Sandra
Estephane, Jane 
Deshayes, Christian
Chantegrel , Bernard
Nasser, William
Queneau, Yves
Reverchon, Sylvie
Doutheau, Alain
Affiliations: Department of Chemical Engineering 
Keywords: Quorum sensing
Vibrio fischeri
Issue Date: 2006
Part of: Bioorganic & medicinal Chemistry
Volume: 14
Issue: 14
Start page: 4781
End page: 4791
A series of 15 racemic alkyl- and aryl-N-substituted ureas, derived from homoserine lactone, were synthesized and tested for their ability to competitively inhibit the action of 3-oxohexanoyl-l-homoserine lactone, the natural inducer of bioluminescence in the bacterium Vibrio fischeri. N-alkyl ureas with an alkyl chain of at least 4 carbon atoms, as well as certain ureas bearing a phenyl group at the extremity of the alkyl chain, were found to be significant antagonists. In the case of N-butyl urea, it has been shown that the antagonist activity was related to the inhibition of the dimerisation of the N-terminal domain of ExpR, a protein of the receptor LuxR family. Molecular modelling suggested that this would result from the formation of an additional hydrogen bond in the protein acylhomoserine lactone binding cavity.
DOI: 10.1016/j.bmc.2006.03.017
Ezproxy URL: Link to full text
Type: Journal Article
Appears in Collections:Department of Chemical Engineering

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