title: Synthesis and evaluation of the quorum sensing inhibitory effect of substituted triazolyldihydrofuranones.
abstract: Acylhomoserine lactone (AHL) analogues in which the amide function is replaced by a triazole group were synthesized and evaluated for their effect on quorum sensing (QS) and biofilm formation in Burkholderia cenocepacia and Pseudomonas aeruginosa. In addition, the influence of the length of the acyl-mimicking chain was investigated. The compounds showed selectivity between two different AHL QS systems. 3-(1H-1,2,3-Triazol-1-yl)dihydrofuran-2(3H)-ones, in which the 4-substituent best resembled the acyl chain of the native AHL molecule exhibited significant QS agonistic and antagonistic activities. Replacing this aliphatic substituent by a phenyl-containing moiety resulted in active inhibitors of QS. The most active compounds showed biofilm inhibitory as well as biofilm eradicating activities in both test organisms.
authors: Laboratory of Pharmaceutical Microbiology, Ghent University, Harelbekestraat 72, B-9000 Ghent, Belgium. Gilles.brackman@UGent.be
authors: Gilles
authors: G
authors: Brackman
authors: Martijn
authors: M
authors: Risseeuw
authors: Shari
authors: S
authors: Celen
authors: Paul
authors: P
authors: Cos
authors: Louis
authors: L
authors: Maes
authors: Hans J
authors: HJ
authors: Nelis
authors: Serge
authors: S
authors: Van Calenbergh
authors: Tom
authors: T
authors: Coenye
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D018441:Biofilms / Q000187:drug effects; D057508:Burkholderia cenocepacia / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D053038:Quorum Sensing / Q000187:drug effects*; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: C576630:3-(1H-1,2,3-triazol-1-yl)dihydrofuran-2(3H)-one; D000900:Anti-Bacterial Agents; D005663:Furans; D014230:Triazoles