Please use this identifier to cite or link to this item: https://scholarhub.balamand.edu.lb/handle/uob/2291
Title: N-Acyl-3-amino-5H-furanone derivatives as new inhibitors of LuxR-dependent quorum sensing : Synthesis, biological evaluation and binding mode study
Authors: Estephane, Jane 
Dauvergne, Julien
Soul
Reverchon, Sylvie
Queneau, Yves
Doutheau, Alain
Affiliations: Department of Chemical Engineering 
Keywords: Quorum sensing
AHLs
LuxR
Antagonist
V. fischeri
Molecular modelling
Docking
Issue Date: 2008
Part of: Bioorganic & medicinal chemistry letters
Volume: 18
Issue: 15
Start page: 4321
End page: 4324
Abstract: 
New N-acyl homoserine lactone analogues, N-acyl-3-amino-5H-furanone derivatives and some 4-halogeno counterparts, were synthesised and tested for their ability to modulate LuxR-dependent bacterial quorum sensing. Both types of analogues proved to be inhibitors, the halogenated compounds being significantly more active. Molecular modelling suggested that the conjugated enamide group induces two preferential conformations leading to specific binding modes. In addition, the presence of the halogen atom could enhance the fitting of the lactone ring through specific interactions with strictly conserved or conservatively replaceable residues in the LuxR protein family, namely Asp79, Trp94 and Ile81.
URI: https://scholarhub.balamand.edu.lb/handle/uob/2291
DOI: 10.1016/j.bmcl.2008.06.090
Ezproxy URL: Link to full text
Type: Journal Article
Appears in Collections:Department of Chemical Engineering

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