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Bioorg Med Chem. 2006 Jul 15;14(14):4781-91. Epub 2006 Mar 29.

Synthesis and biological evaluation of homoserine lactone derived ureas as antagonists of bacterial quorum sensing.

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Laboratoire de Chimie Organique, UMR CNRS-UCBL-INSA 5181, Institut National des Sciences Appliquées, 20 avenue A. Einstein, 69621 Villeurbanne, France.


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.

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