NDLI: Synthesis and Biological Evaluation of Triazole-Containing N-Acyl Homoserine Lactones as Quorum Sensing Modulators

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Synthesis and Biological Evaluation of Triazole-Containing N-Acyl Homoserine Lactones as Quorum Sensing Modulators

Content Provider	PubMed Central
Author	Stacy, Danielle M. Le Quement, Sebastian T. Hansen, Casper L. Clausen, Janie W. Tim, Tolker-nielsen Brummond, Jacob W. Michael, Givskov Nielsen, Thomas E. Blackwell, Helen E.
Abstract	Many bacterial species are capable of assessing their local population densities through a cell-cell signaling mechanism termed quorum sensing (QS). This intercellular communication process is mediated by small molecule or peptide ligands and their cognate protein receptors. Numerous pathogens use QS to initiate virulence once they achieve a threshold cell number on a host. Consequently, approaches to intercept QS have attracted considerable attention as potential anti-infective therapies. Our interest in the development of small molecule tools to modulate QS pathways motivated us to evaluate triazole-containing analogs of natural N-acyl L-homoserine lactone (AHL) signals as non-native QS agonists and antagonists in Gram-negative bacteria. We synthesized 72 triazole derivatives of five broad structure types in high yields and purities using efficient Cu(I)-catalyzed azide-alkyne couplings. These compounds were evaluated for their ability to activate or inhibit two QS receptors from two prevalent pathogens – LasR from Pseudomonas aeruginosa and AbaR from Acinetobacter baumannii – using bacterial reporter strains. Several triazole derivatives were identified that were capable of strongly modulating the activity of LasR and AbaR. These compounds represent a new and synthetically accessible class of AHL analogs, and could find utility as chemical tools to study QS and its role in bacterial virulence.
Related Links	http://dx.doi.org/10.1039/c2ob27155a
Ending Page	954
Page Count	17
Starting Page	938
File Format	PDF
ISSN	14770520
e-ISSN	14770539
Journal	Organic & biomolecular chemistry
Issue Number	6
Volume Number	11
Language	English
Publisher Date	2013-01-01
Access Restriction	Open
Subject Keyword	Physical and Theoretical Chemistry Organic Chemistry Biochemistry Research in Higher Education
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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