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Structure-activity relationship of cinnamaldehyde analogs as inhibitors of AI-2 based quorum sensing and their effect on virulence of vibrio spp

Gilles Brackman UGent, Shari Celen UGent, Ulrik Hillaert UGent, Serge Van Calenbergh UGent, Paul Cos, Louis Maes, Hans Nelis UGent and Tom Coenye UGent (2011) PLOS ONE. 6(1).
abstract
Background: Many bacteria, including Vibrio spp., regulate virulence gene expression in a cell-density dependent way through a communication process termed quorum sensing (QS). Hence, interfering with QS could be a valuable novel antipathogenic strategy. Cinnamaldehyde has previously been shown to inhibit QS-regulated virulence by decreasing the DNA-binding ability of the QS response regulator LuxR. However, little is known about the structure-activity relationship of cinnamaldehyde analogs. Methodology/Principal Findings: By evaluating the QS inhibitory activity of a series of cinnamaldehyde analogs, structural elements critical for autoinducer-2 QS inhibition were identified. These include an alpha, beta unsaturated acyl group capable of reacting as Michael acceptor connected to a hydrophobic moiety and a partially negative charge. The most active cinnamaldehyde analogs were found to affect the starvation response, biofilm formation, pigment production and protease production in Vibrio spp in vitro, while exhibiting low cytotoxicity. In addition, these compounds significantly increased the survival of the nematode Caenorhabditis elegans infected with Vibrio anguillarum, Vibrio harveyi and Vibrio vulnificus. Conclusions/Significance: Several new and more active cinnamaldehyde analogs were discovered and they were shown to affect Vibrio spp. virulence factor production in vitro and in vivo. Although ligands for LuxR have not been identified so far, the nature of different cinnamaldehyde analogs and their effect on the DNA binding ability of LuxR suggest that these compounds act as LuxR-ligands.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
PROTEIN, SEQUENCE, LUMINESCENCE, AUTOINDUCER, EXPRESSION
journal title
PLOS ONE
PLoS One
volume
6
issue
1
article_number
e16084
pages
10 pages
Web of Science type
Article
Web of Science id
000286515000017
JCR category
BIOLOGY
JCR impact factor
4.092 (2011)
JCR rank
12/84 (2011)
JCR quartile
1 (2011)
ISSN
1932-6203
DOI
10.1371/journal.pone.0016084
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1179438
handle
http://hdl.handle.net/1854/LU-1179438
date created
2011-03-01 15:18:23
date last changed
2011-04-01 11:28:53
@article{1179438,
  abstract     = {Background: Many bacteria, including Vibrio spp., regulate virulence gene expression in a cell-density dependent way through a communication process termed quorum sensing (QS). Hence, interfering with QS could be a valuable novel antipathogenic strategy. Cinnamaldehyde has previously been shown to inhibit QS-regulated virulence by decreasing the DNA-binding ability of the QS response regulator LuxR. However, little is known about the structure-activity relationship of cinnamaldehyde analogs. Methodology/Principal Findings: By evaluating the QS inhibitory activity of a series of cinnamaldehyde analogs, structural elements critical for autoinducer-2 QS inhibition were identified. These include an alpha, beta unsaturated acyl group capable of reacting as Michael acceptor connected to a hydrophobic moiety and a partially negative charge. The most active cinnamaldehyde analogs were found to affect the starvation response, biofilm formation, pigment production and protease production in Vibrio spp in vitro, while exhibiting low cytotoxicity. In addition, these compounds significantly increased the survival of the nematode Caenorhabditis elegans infected with Vibrio anguillarum, Vibrio harveyi and Vibrio vulnificus. Conclusions/Significance: Several new and more active cinnamaldehyde analogs were discovered and they were shown to affect Vibrio spp. virulence factor production in vitro and in vivo. Although ligands for LuxR have not been identified so far, the nature of different cinnamaldehyde analogs and their effect on the DNA binding ability of LuxR suggest that these compounds act as LuxR-ligands.},
  articleno    = {e16084},
  author       = {Brackman, Gilles and Celen, Shari and Hillaert, Ulrik and Van Calenbergh, Serge and Cos, Paul and Maes, Louis and Nelis, Hans and Coenye, Tom},
  issn         = {1932-6203},
  journal      = {PLOS ONE},
  keyword      = {PROTEIN,SEQUENCE,LUMINESCENCE,AUTOINDUCER,EXPRESSION},
  language     = {eng},
  number       = {1},
  pages        = {10},
  title        = {Structure-activity relationship of cinnamaldehyde analogs as inhibitors of AI-2 based quorum sensing and their effect on virulence of vibrio spp},
  url          = {http://dx.doi.org/10.1371/journal.pone.0016084},
  volume       = {6},
  year         = {2011},
}

Chicago
Brackman, Gilles, Shari Celen, Ulrik Hillaert, Serge Van Calenbergh, Paul Cos, Louis Maes, Hans Nelis, and Tom Coenye. 2011. “Structure-activity Relationship of Cinnamaldehyde Analogs as Inhibitors of AI-2 Based Quorum Sensing and Their Effect on Virulence of Vibrio Spp.” Plos One 6 (1).
APA
Brackman, G., Celen, S., Hillaert, U., Van Calenbergh, S., Cos, P., Maes, L., Nelis, H., et al. (2011). Structure-activity relationship of cinnamaldehyde analogs as inhibitors of AI-2 based quorum sensing and their effect on virulence of vibrio spp. PLOS ONE, 6(1).
Vancouver
1.
Brackman G, Celen S, Hillaert U, Van Calenbergh S, Cos P, Maes L, et al. Structure-activity relationship of cinnamaldehyde analogs as inhibitors of AI-2 based quorum sensing and their effect on virulence of vibrio spp. PLOS ONE. 2011;6(1).
MLA
Brackman, Gilles, Shari Celen, Ulrik Hillaert, et al. “Structure-activity Relationship of Cinnamaldehyde Analogs as Inhibitors of AI-2 Based Quorum Sensing and Their Effect on Virulence of Vibrio Spp.” PLOS ONE 6.1 (2011): n. pag. Print.