title: Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators.
abstract: New analogues of N-acyl-homoserine-lactone (AHL), in which the amide was replaced by a triazole or tetrazole ring, were prepared and tested for their activity as LuxR-dependent QS modulators. Several compounds showed a level of antagonistic or agonistic activity, notably some 1,4-triazolic and 1,5-tetrazolic derivatives, whereas the 2,5-tetrazolic compounds were inactive. In 1,5-tetrazoles, substituted with butyrolactone and an alkyl chain, the activity was reversed, depending on the connection between the lactone and the tetrazole. The C-N connected compounds were agonists whereas the C-C connected ones were antagonists.
authors: INSA Lyon, ICBMS, Bât J. Verne, 20 av A. Einstein, 69621 Villeurbanne Cedex, France.
authors: Mohamad
authors: M
authors: Sabbah
authors: Fanny
authors: F
authors: Fontaine
authors: Lucie
authors: L
authors: Grand
authors: Mohamed
authors: M
authors: Boukraa
authors: Mohamed L
authors: ML
authors: Efrit
authors: Alain
authors: A
authors: Doutheau
authors: Laurent
authors: L
authors: Soulère
authors: Yves
authors: Y
authors: Queneau
mesh_terms: D006714:Homoserine / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D012097:Repressor Proteins / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship; D013777:Tetrazoles / Q000737:chemistry*; D015534:Trans-Activators / Q000037:antagonists & inhibitors*; D014230:Triazoles / Q000737:chemistry*
chemical_list: D007783:Lactones; D012097:Repressor Proteins; D013777:Tetrazoles; D015534:Trans-Activators; D014230:Triazoles; C064778:LuxR autoinducer binding proteins; C045574:1H-tetrazole; D006714:Homoserine