Synthesis and biological evaluation of novel N-?-haloacylated homoserine lactones as quorum sensing modulators.

ABSTRACT: Novel N-?-haloacylated homoserine lactones, in which a halogen atom was introduced at the ?-position of the carbonyl function of the N-acyl chain, have been studied as quorum sensing (QS) modulators and compared with a library of natural N-acylated homoserine lactones (AHLs). The series of novel analogues consists of ?-chloro, ?-bromo and ?-iodo AHL analogues. Furthermore, the biological QS activity of the synthetic AHL analogues compared to the natural AHLs was evaluated. Halogenated analogues demonstrated a reduced activity in the Escherichia coli JB523 bioassay, with the ?-iodo lactones being the less active ones and the ?-chloro AHLs the most potent QS agonists. Most of the ?-haloacylated analogues did not exhibit a significant reduction when tested in the QS inhibition test. Therefore, these novel analogues could be utilized as chemical probes for QS structure-activity studies.

SUBMITTER: Syrpas M 

PROVIDER: S-EPMC4222389 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature