N-Sulfonyl homoserine lactones as antagonists of bacterial quorum sensing. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Bioorganic and Medicinal Chemistry Letters Année : 2004

N-Sulfonyl homoserine lactones as antagonists of bacterial quorum sensing.

Résumé

A series of 11 new analogues of N-acylhomoserine lactones in which the carboxamide bond was replaced by a sulfonamide one, has been synthesised. These compounds were evaluated for their ability to competitively inhibit the action of 3-oxohexanoyl-L-homoserine lactone, the natural ligand of the quorum sensing transcriptional regulator LuxR, which in turn activates expression of bioluminescence in the model bacterium Vibrio fischeri. Several compounds were found to display antagonist activity. Molecular modeling suggests that the latter prevent a cascade of structural rearrangements necessary for the formation of the active LuxR dimer.A series of 11 new analogues of N-acylhomoserine lactones in which the carboxamide bond was replaced by a sulfonamide one, has been synthesised. These compounds were evaluated for their ability to competitively inhibit the action of 3-oxohexanoyl-L-homoserine lactone, the natural ligand of the quorum sensing transcriptional regulator LuxR, which in turn activates expression of bioluminescence in the model bacterium Vibrio fischeri. Several compounds were found to display antagonist activity. Molecular modeling suggests that the latter prevent a cascade of structural rearrangements necessary for the formation of the active LuxR dimer.
Fichier non déposé

Dates et versions

hal-00313537 , version 1 (27-08-2008)

Identifiants

  • HAL Id : hal-00313537 , version 1

Citer

S. Castang, B. Chantegrel, C. Deshayes, R. Dolmazon, P. Gouet, et al.. N-Sulfonyl homoserine lactones as antagonists of bacterial quorum sensing.. Bioorganic and Medicinal Chemistry Letters, 2004, 14, pp.5145-5149. ⟨hal-00313537⟩
22 Consultations
0 Téléchargements

Partager

Gmail Facebook X LinkedIn More