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|Title:||Synthesis and biological evaluation of homoserine lactone derived ureas as antagonists of bacterial quorum sensing||Authors:||Frezza, Marine
Chantegrel , Bernard
|Affiliations:||Department of Chemical Engineering||Keywords:||Quorum sensing
|Issue Date:||2006||Part of:||Bioorganic & medicinal Chemistry||Volume:||14||Issue:||14||Start page:||4781||End page:||4791||Abstract:||
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.
|URI:||https://scholarhub.balamand.edu.lb/handle/uob/2614||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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