scholarly journals Comparative Analyses ofN-Acylated Homoserine Lactones Reveal Unique Structural Features that Dictate Their Ability to Activate or Inhibit Quorum Sensing

ChemBioChem ◽  
2008 ◽  
Vol 9 (3) ◽  
pp. 389-400 ◽  
Author(s):  
Grant D. Geske ◽  
Jennifer C. O'Neill ◽  
David M. Miller ◽  
Rachel J. Wezeman ◽  
Margrith E. Mattmann ◽  
...  
Keyword(s):  
Quorum Sensing ◽  
Structural Features ◽  
Homoserine Lactones ◽  
Comparative Analyses ◽  
Acylated Homoserine Lactones

Petunidin as a competitive inhibitor of acylated homoserine lactones in Klebsiella pneumoniae

RSC Advances ◽  
2016 ◽  
Vol 6 (4) ◽  
pp. 2592-2601 ◽  
Author(s):  
Venkadesaperumal Gopu ◽  
Chetan Kumar Meena ◽  
Ayaluru Murali ◽  
Prathapkumar Halady Shetty
Keyword(s):  
Quorum Sensing ◽  
Klebsiella Pneumoniae ◽  
Bacterial Species ◽  
Competitive Inhibitor ◽  
Phenotypic Characteristics ◽  
Homoserine Lactones ◽  
Acylated Homoserine Lactones

Most of the bacterial species communicate with each other through a mechanism called Quorum Sensing (QS) to regulate their phenotypic characteristics.

Rational design and synthesis of new quorum-sensing inhibitors derived from acylated homoserine lactones and natural products from garlic

2005 ◽  
Vol 3 (2) ◽  
pp. 253-262 ◽  
Author(s):  
Tobias Persson ◽  
Thomas H. Hansen ◽  
Thomas B. Rasmussen ◽  
Mette E. Skindersø ◽  
Michael Givskov ◽  
...  
Keyword(s):  
Natural Products ◽  
Quorum Sensing ◽  
Rational Design ◽  
Homoserine Lactones ◽  
Design And Synthesis ◽  
Quorum Sensing Inhibitors ◽  
Acylated Homoserine Lactones

scholarly journals Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators

2014 ◽  
Vol 10 ◽  
pp. 2539-2549 ◽  
Author(s):  
Michail Syrpas ◽  
Ewout Ruysbergh ◽  
Christian V Stevens ◽  
Norbert De Kimpe ◽  
Sven Mangelinckx
Keyword(s):  
Quorum Sensing ◽  
Acyl Chain ◽  
Biological Evaluation ◽  
Chemical Probes ◽  
Homoserine Lactones ◽  
Structure Activity ◽  
Acylated Homoserine Lactones ◽  
Synthesis And Biological Evaluation ◽  
Reduced Activity ◽  
Carbonyl Function

Novel N-α-haloacylated homoserine lactones, in which a halogen atom was introduced at the α-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 α-chloro, α-bromo and α-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 α-iodo lactones being the less active ones and the α-chloro AHLs the most potent QS agonists. Most of the α-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.

scholarly journals Possible Quorum Sensing in Marine Snow Bacteria: Production of Acylated Homoserine Lactones by Roseobacter Strains Isolated from Marine Snow

2002 ◽  
Vol 68 (8) ◽  
pp. 4111-4116 ◽  
Author(s):  
Lone Gram ◽  
Hans-Peter Grossart ◽  
Andrea Schlingloff ◽  
Thomas Kiørboe
Keyword(s):  
Quorum Sensing ◽  
Antibiotic Production ◽  
Phenotypic Traits ◽  
Marine Snow ◽  
Marine Microorganisms ◽  
Reporter System ◽  
Communication Signals ◽  
Homoserine Lactones ◽  
Gene Sequence Analysis ◽  
Acylated Homoserine Lactones

ABSTRACT We report here, for the first time, that bacteria associated with marine snow produce communication signals involved in quorum sensing in gram-negative bacteria. Four of 43 marine microorganisms isolated from marine snow were found to produce acylated homoserine lactones (AHLs) in well diffusion and thin-layer chromatographic assays based on the Agrobacterium tumefaciens reporter system. Three of the AHL-producing strains were identified by 16S ribosomal DNA gene sequence analysis as Roseobacter spp., and this is the first report of AHL production by these α-Proteobacteria. It is likely that AHLs in Roseobacter species and other marine snow bacteria govern phenotypic traits (biofilm formation, exoenzyme production, and antibiotic production) which are required mainly when the population reaches high densities, e.g., in the marine snow community.

scholarly journals Biofilms on Indwelling Urethral Catheters Produce Quorum-Sensing Signal Molecules In Situ and In Vitro

1998 ◽  
Vol 64 (9) ◽  
pp. 3486-3490 ◽  
Author(s):  
David J. Stickler ◽  
Nicola S. Morris ◽  
Robert J. C. McLean ◽  
Clay Fuqua
Keyword(s):  
Quorum Sensing ◽  
Signal Molecules ◽  
Gram Negative Bacteria ◽  
Feeding Assay ◽  
Gram Negative ◽  
Homoserine Lactones ◽  
Acylated Homoserine Lactones

ABSTRACT Acylated homoserine lactones (AHLs) are chemical signals that mediate population density-dependent (quorum-sensing) gene expression in numerous gram-negative bacteria. In this study, gram-negative bacilli isolated from catheters were screened for AHL production by a cross-feeding assay utilizing an AHL-responsive Agrobacterium tumefaciens reporter strain. Positive reactions were obtained from 14 isolates of Pseudomonas aeruginosa; negative or weakly positive reactions were recorded for isolates of five other species. P. aeruginosa biofilms were then produced on catheters in a physical model of the bladder. Sections of colonized all-silicone catheters gave positive reactions for the quorum-sensing signal molecules as did sections that had been cleaned of biofilm and autoclaved. Control sections of unused catheters were negative in the tests. Sections from four of nine catheters that had been freshly removed from patients gave positive reactions for AHLs. Cleaned autoclaved sections of three of these catheters also gave strongly positive reactions for AHLs. These results demonstrate that AHLs are produced by biofilms as they develop on the catheters both in vitro in the model and in vivo in the patient’s bladder. They represent the first demonstration of AHL production by biofilms in a clinical setting.

scholarly journals Quorum sensing signal molecules (acylated homoserine lactones) in Gram-negative fish pathogenic bacteria

2005 ◽  
Vol 65 ◽  
pp. 43-52 ◽  
Author(s):  
JB Bruhn ◽  
I Dalsgaard ◽  
KF Nielsen ◽  
C Buchholtz ◽  
JL Larsen ◽  
...  
Keyword(s):  
Quorum Sensing ◽  
Pathogenic Bacteria ◽  
Signal Molecules ◽  
Gram Negative ◽  
Homoserine Lactones ◽  
Acylated Homoserine Lactones

scholarly journals Caenorhabditis elegans Senses Bacterial Autoinducers

2006 ◽  
Vol 72 (7) ◽  
pp. 5135-5137 ◽  
Author(s):  
Elmus Beale ◽  
Guigen Li ◽  
Man-Wah Tan ◽  
Kendra P. Rumbaugh
Keyword(s):  
Pseudomonas Aeruginosa ◽  
Caenorhabditis Elegans ◽  
Quorum Sensing ◽  
Virulence Factors ◽  
Homoserine Lactones ◽  
C Elegans ◽  
Acylated Homoserine Lactones

ABSTRACT Pseudomonas aeruginosa uses virulence factors controlled by quorum sensing (QS) to kill Caenorhabditis elegans. Here we show that C. elegans is attracted to the acylated homoserine lactones (AHSLs) that mediate QS in P. aeruginosa. Our data also indicate that C. elegans can distinguish AHSLs and may use them to mediate aversive or attractive learning.

scholarly journals Non-native acylated homoserine lactones reveal that LuxIR quorum sensing promotes symbiont stability

2013 ◽  
Vol 16 (8) ◽  
pp. 2623-2634 ◽  
Author(s):  
Sarah V. Studer ◽  
Julia A. Schwartzman ◽  
Jessica S. Ho ◽  
Grant D. Geske ◽  
Helen E. Blackwell ◽  
...  
Keyword(s):  
Quorum Sensing ◽  
Homoserine Lactones ◽  
Acylated Homoserine Lactones

scholarly journals A Marine Mesorhizobium sp. Produces Structurally Novel Long-Chain N-Acyl-l-Homoserine Lactones

2007 ◽  
Vol 73 (11) ◽  
pp. 3587-3594 ◽  
Author(s):  
Anja Krick ◽  
Stefan Kehraus ◽  
Leo Eberl ◽  
Kathrin Riedel ◽  
Heidrun Anke ◽  
...  
Keyword(s):  
Quorum Sensing ◽  
Solid Phase ◽  
Homoserine Lactone ◽  
Signal Molecules ◽  
Cytotoxic Activities ◽  
Rrna Gene ◽  
Liquid Chromatography Mass Spectrometry ◽  
Homoserine Lactones ◽  
Chain Lengths ◽  
Acylated Homoserine Lactones

ABSTRACT Our study focused on a Mesorhizobium sp. that is phylogenetically affiliated by 16S rRNA gene sequence to other marine and saline bacteria of this genus. Liquid chromatography-mass spectrometry investigations of the extract obtained from solid-phase extraction of cultures of this bacterium indicated the presence of several N-acyl homoserine lactones (AHLs), with chain lengths of C10 to C16. Chromatographic separation of the active bacterial extract yielded extraordinarily large amounts of two unprecedented acylated homoserine lactones, 5-cis-3-oxo-C12-homoserine lactone (5-cis-3-oxo-C12-HSL) (compound 1) and 5-cis-C12-HSL (compound 2). Quorum-sensing activity of compounds 1 and 2 was shown in two different biosensor systems [Escherichia coli MT102(pSB403) and Pseudomonas putida F117(pKR-C12)]. Furthermore, it was shown that both compounds can restore protease and pyoverdin production of an AHL-deficient Pseudomonas aeruginosa PAO1 lasI rhlI double mutant, suggesting that these signal molecules maybe used for intergenus signaling. In conclusion, these data indicate that the quorum-sensing activity of compounds 1 and 2 is modulated by the chain length and functional groups of the acyl moiety. Additionally, compound 1 showed antibacterial and cytotoxic activities.

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