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1.
Nature ; 450(7171): 883-6, 2007 Dec 06.
Artigo em Inglês | MEDLINE | ID: mdl-18004304

RESUMO

Vibrio cholerae, the causative agent of the human disease cholera, uses cell-to-cell communication to control pathogenicity and biofilm formation. This process, known as quorum sensing, relies on the secretion and detection of signalling molecules called autoinducers. At low cell density V. cholerae activates the expression of virulence factors and forms biofilms. At high cell density the accumulation of two quorum-sensing autoinducers represses these traits. These two autoinducers, cholerae autoinducer-1 (CAI-1) and autoinducer-2 (AI-2), function synergistically to control gene regulation, although CAI-1 is the stronger of the two signals. V. cholerae AI-2 is the furanosyl borate diester (2S,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran borate. Here we describe the purification of CAI-1 and identify the molecule as (S)-3-hydroxytridecan-4-one, a new type of bacterial autoinducer. We provide a synthetic route to both the R and S isomers of CAI-1 as well as simple homologues, and we evaluate their relative activities. Synthetic (S)-3-hydroxytridecan-4-one functions as effectively as natural CAI-1 in repressing production of the canonical virulence factor TCP (toxin co-regulated pilus). These findings suggest that CAI-1 could be used as a therapy to prevent cholera infection and, furthermore, that strategies to manipulate bacterial quorum sensing hold promise in the clinical arena.


Assuntos
Cetonas/isolamento & purificação , Cetonas/farmacologia , Percepção de Quorum , Vibrio cholerae/metabolismo , Vibrio cholerae/patogenicidade , Fatores de Virulência/biossíntese , Biofilmes , Boratos , Contagem de Colônia Microbiana , Escherichia coli , Furanos , Cetonas/síntese química , Cetonas/química , Espectroscopia de Ressonância Magnética , Modelos Biológicos , Vibrio cholerae/citologia , Fatores de Virulência/genética
2.
ACS Chem Biol ; 2(5): 293-5, 2007 May 22.
Artigo em Inglês | MEDLINE | ID: mdl-17518429

RESUMO

Small-molecule agonists and antagonists of bacterial quorum sensing can enhance our understanding of this form of cell-cell communication. A recent effort has discovered effective modulators of the autoinducer-1 circuit for bacterial quorum sensing by the synthesis and evaluation of a small library of aryl-substituted acyl-homoserine lactone analogues. This series highlights the sensitivity to structure of the contrasting responses of agonism and antagonism of the natural signal and identifies an analogue that provokes the same response as the natural signal but at 10-fold lower concentration, a "superagonist".


Assuntos
4-Butirolactona/análogos & derivados , Antibacterianos , Bactérias Gram-Negativas , 4-Butirolactona/agonistas , 4-Butirolactona/antagonistas & inibidores , Aliivibrio fischeri/efeitos dos fármacos , Aliivibrio fischeri/genética , Aliivibrio fischeri/metabolismo , Antibacterianos/química , Antibacterianos/farmacologia , Regulação Bacteriana da Expressão Gênica/efeitos dos fármacos , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Negativas/genética , Bactérias Gram-Negativas/metabolismo , Ligantes
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