Pyrogallol and its analogs can antagonize bacterial quorum sensing in Vibrio harveyi

Ni, Nanting; Choudhary, Gaurav S.; Li, Minyong; Wang, Binghe

doi:10.1016/j.bmcl.2008.01.081

Cited by 92 publications

(54 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…With the concept of molecular mimicry in hand and the goal of identifying novel antagonists of AI-2 signaling, Wang and colleagues published a series of papers in which they screened a large number of compounds that they believed would have the potential to complex with the V. harveyi receptor LuxP (131,204,205). They chose to focus on compounds with molecular structures significantly different from those of the previously examined nonaromatic cyclic polyols which generally exhibited agonist activity (206)(207)(208).…”

Section: Inhibition Of Signal Detection Synthetic Signal Analogues Anmentioning

confidence: 99%

“…They chose to focus on compounds with molecular structures significantly different from those of the previously examined nonaromatic cyclic polyols which generally exhibited agonist activity (206)(207)(208). The first two screens involved diol-containing compounds, which have the ability to complex with boric acid, and native boronic acid compounds (131,205), all chosen due to their similarities to the 2,3-borate diester form of AI-2 recognized by LuxP (Fig. 2) (35, 36).…”

Section: Inhibition Of Signal Detection Synthetic Signal Analogues Anmentioning

confidence: 99%

See 1 more Smart Citation

Exploiting Quorum Sensing To Confuse Bacterial Pathogens

LaSarre

Federle

2013

Microbiol Mol Biol Rev

677

556

View full text Add to dashboard Cite

SUMMARY Cell-cell communication, or quorum sensing, is a widespread phenomenon in bacteria that is used to coordinate gene expression among local populations. Its use by bacterial pathogens to regulate genes that promote invasion, defense, and spread has been particularly well documented. With the ongoing emergence of antibiotic-resistant pathogens, there is a current need for development of alternative therapeutic strategies. An antivirulence approach by which quorum sensing is impeded has caught on as a viable means to manipulate bacterial processes, especially pathogenic traits that are harmful to human and animal health and agricultural productivity. The identification and development of chemical compounds and enzymes that facilitate quorum-sensing inhibition (QSI) by targeting signaling molecules, signal biogenesis, or signal detection are reviewed here. Overall, the evidence suggests that QSI therapy may be efficacious against some, but not necessarily all, bacterial pathogens, and several failures and ongoing concerns that may steer future studies in productive directions are discussed. Nevertheless, various QSI successes have rightfully perpetuated excitement surrounding new potential therapies, and this review highlights promising QSI leads in disrupting pathogenesis in both plants and animals.

show abstract

Section: Inhibition Of Signal Detection Synthetic Signal Analogues Anmentioning

confidence: 99%

Section: Inhibition Of Signal Detection Synthetic Signal Analogues Anmentioning

confidence: 99%

Exploiting Quorum Sensing To Confuse Bacterial Pathogens

LaSarre

Federle

2013

Microbiol Mol Biol Rev

677

556

View full text Add to dashboard Cite

show abstract

“…Although several compounds inhibit the AI-2 QS system, there are few reports of QS inhibitors targeting LuxPQ. Phenylboronic acids, pyrogallol derivatives and 2-(2-thienylsulfonyl)ethanethioamide, previously reported to block the AI-2 QS system at the level of LuxPQ (Li et al, 2008;Ni et al, 2008a, b), were at best as active as LMC-21. None of these compounds has been previously evaluated for its effect on AI-2-related virulence.…”

Section: Discussionmentioning

confidence: 91%

AI-2 quorum-sensing inhibitors affect the starvation response and reduce virulence in several Vibrio species, most likely by interfering with LuxPQ

et al. 2009

View full text Add to dashboard Cite

The increase of disease outbreaks caused by Vibrio species in aquatic organisms as well as in humans, together with the emergence of antibiotic resistance in Vibrio species, has led to a growing interest in alternative disease control measures. Quorum sensing (QS) is a mechanism for regulating microbial gene expression in a cell density-dependent way. While there is good evidence for the involvement of auto-inducer 2 (AI-2)-based interspecies QS in the control of virulence in multiple Vibrio species, only few inhibitors of this system are known. From the screening of a small panel of nucleoside analogues for their ability to disturb AI-2-based QS, an adenosine derivative with a p-methoxyphenylpropionamide moiety at C-39 emerged as a promising hit. Its mechanism of inhibition was elucidated by measuring the effect on bioluminescence in a series of Vibrio harveyi AI-2 QS mutants. Our results indicate that this compound, as well as a truncated analogue lacking the adenine base, block AI-2-based QS without interfering with bacterial growth. The active compounds affected neither the bioluminescence system as such nor the production of AI-2, but most likely interfered with the signal transduction pathway at the level of LuxPQ in V. harveyi. The most active nucleoside analogue (designated LMC-21) was found to reduce the Vibrio species starvation response, to affect biofilm formation in Vibrio anguillarum, Vibrio vulnificus and Vibrio cholerae, to reduce pigment and protease production in V. anguillarum, and to protect gnotobiotic Artemia from V. harveyi-induced mortality. INTRODUCTIONVibrio species are ubiquitous in marine environments worldwide (Igbinosa & Okoh, 2008). As opportunistic pathogens they can cause mild to severe infections in humans and marine animals. Vibriosis is one of the most prevalent fish diseases, mainly caused by Vibrio anguillarum, Vibrio alginolyticus, Vibrio parahaemolyticus, Vibrio harveyi and Vibrio campbellii (Garcia et al., 1997;Austin & Zhang, 2006). Other Vibrio species are pathogenic for humans. Vibrio vulnificus is associated with gastrointestinal infections primarily following the consumption of raw and undercooked seafood, but it can also cause wound or soft-tissue infections (Bross et al., 2007). In addition, systemic V. vulnificus infections are notorious for their high mortality rate (Chiang & Chuang, 2003). Vibrio cholerae is responsible for pandemic and epidemic outbreaks of cholera (Griffith et al., 2006). V. cholerae serotype O1 causes the majority of the outbreaks worldwide, while the O139 serotype has only been detected in South-East and East Asia (Sack et al., 2004;Griffith et al., 2006). Cellcell communication (quorum sensing; QS) in Vibrio species plays an important role in virulence. QS in Vibrio species involves three types of signal molecules. NAcylhomoserine lactones (AHLs) are used in the LuxM/N QS system, cholera auto-inducer 1 (CAI-1) in the CqsA/S system and auto-inducer 2 (AI-2) in the LuxS/PQ QS system (Bassler et al., 1993(Bassler et al., , 1997Higgins et al., ...

show abstract

“…Persson et al (2005) identified several active compounds from garlic extracts that exhibited LuxR antagonist activity in Vibrio fischeri and P. aeruginosa PAO1, cyclic thioacetal and cyclic disulphide being the most effective compounds. Another compound present in garlic extracts is pyrogallol, which showed antagonism activity against AI-2 mediated QS in V. harveyi in a micromolar range without any cytotoxic effect (Ni, Choudhary, Li, & Wang, 2008). Ajoene, a sulphur-rich molecule from garlic, has been proven as a QSI against AHL: acyl homoserine lactone; EPS: exopolysaccharide; PQS: 2-heptyl-3-hydroxy-4(1H)-quinolone; QS: quorum sensing.…”

Section: Food Phytochemicalsmentioning

confidence: 99%