Design and Synthesis of Macrocyclic Peptomers as Mimics of a Quorum Sensing Signal from <i>Staphylococcus aureus</i>

Fowler, Sarah A.; Stacy, Danielle M.; Blackwell, Helen E.

doi:10.1021/ol800908h

Cited by 77 publications

(63 citation statements)

References 30 publications

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“…Furthermore, addition of trAIP-II to S. aureus cultures reduced production of ␦-toxin, a known virulence factor (130), indicating a reduction in virulence potential. Separately, 14 macrocyclic peptide-peptoid hybrid molecules lacking thioester linkages were designed as AIP-1 analogues, and one was found to alter S. aureus biofilm formation in vitro, a known AIP-modulated behavior, although the mechanism of action by the molecule was not investigated (223). The most persuasive evidence that AIP analogue inhibitors can be potential antivirulence compounds comes from experiments done in mice.…”

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

689

556

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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.

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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

689

556

View full text Add to dashboard Cite

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“…The RNA-III inhibiting peptide (RIP) 10 inhibits phosphorylation of TRAP leading to reduced biofi lm formation, and RIP has been investigated as an anti-biofi lm agent, successfully preventing infections in multiple animal models (Giacometti et al 2003 ). AIP analogues have also been investigated as antibiofi lm agents; the truncated peptide 11 is a potent AgrC QS antagonist (Chan et al 2004 ), while the peptidomimetic 12 promotes biofi lm formation in S. aureus (Fowler et al 2008 ), and the synthetic RIP derivative FS3 13 ( Fig. 6.2 ) enhances the effi cacy of tigecycline in a rat model of staphylococcal vascular graft infection (Simonetti et al 2013 ).…”

Section: Autoinducing Peptides (Aips)mentioning

confidence: 99%

Innovative Strategies for Combating Biofilm-Based Infections

Melander

2014

Advances in Experimental Medicine and Biology

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“…This fact could be attributed to changes in surface charges during growth due to modifications in the chemical composition of the cell wall in response to environmental conditions, or to an excretion of acid metabolites that neutralizes the negative charges of glutamic and aspartic acid residues (Shakerifard et al, 2009) decreasing the repulsion of surfactin and exposing the hydrophobic aminoacid moieties therefore increasing the hydrophobic interactions and favoring the adhesion. Fowler, Stacy, and Blackwell (2008) suggested that cyclic lipopeptides could increase the adherence of S. aureus since they are analogous to quorum sensing autoinducers that stimulate the adhesion of Staphylococci on surfaces. The reduction on adhesion of S. aureus after the pre-conditioning with rhamnolipid 1.0% can be related with the strong reduction of hydrophobicity of polystyrene combined with charge repulsion.…”

Section: Effect Of Biosurfactants On Bacterial Adhesionmentioning

confidence: 99%

Evaluation of rhamnolipid and surfactin to reduce the adhesion and remove biofilms of individual and mixed cultures of food pathogenic bacteria

Gomes¹,

Nitschke²

2012

Food Control

166

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a b s t r a c tBiofilms represent a great concern for food industry, since they can be a source of persistent contamination leading to food spoilage and to the transmission of diseases. To avoid the adhesion of bacteria and the formation of biofilms, an alternative is the pre-conditioning of surfaces using biosurfactants, microbial compounds that can modify the physicochemical properties of surfaces changing bacterial interactions and consequently adhesion. Different concentrations of the biosurfactants, surfactin from Bacillus subtilis and rhamnolipids from Pseudomonas aeruginosa, were evaluated to reduce the adhesion and to disrupt biofilms of food-borne pathogenic bacteria. Individual cultures and mixed cultures of Staphylococcus aureus, Listeria monocytogenes and Salmonella Enteritidis were studied using polystyrene as the model surface. The pre-conditioning with surfactin 0.25% reduced by 42.0% the adhesion of L. monocytogenes and S. Enteritidis, whereas the treatment using rhamnolipids 1.0% reduced by 57.8% adhesion of L. monocytogenes and by 67.8% adhesion of S. aureus to polystyrene.Biosurfactants were less effective to avoid adhesion of mixed cultures of the bacteria when compared with individual cultures. After 2 h contact with surfactin at 0.1% concentration, the pre-formed biofilms of S. aureus were reduced by 63.7%, L. monocytogenesby 95.9%, S. Enteritidis by 35.5% and the mixed culture biofilm by 58.5%. The rhamnolipids at 0.25% concentration removed 58.5% the biofilm of S. aureus, 26.5% of L. monocytogenes, 23.0% of S. Enteritidis and 24.0% the mixed culture after 2 h contact. In general, the increase in concentration of biosurfactants and in the time of contact decreased biofilm removal percentage. These results suggest that surfactin and rhamnolipids can be explored to control the attachment and to disrupt biofilms of individual and mixed cultures of the food-borne pathogens.

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Design and Synthesis of Macrocyclic Peptomers as Mimics of a Quorum Sensing Signal from Staphylococcus aureus

Cited by 77 publications

References 30 publications

Exploiting Quorum Sensing To Confuse Bacterial Pathogens

Exploiting Quorum Sensing To Confuse Bacterial Pathogens

Innovative Strategies for Combating Biofilm-Based Infections

Evaluation of rhamnolipid and surfactin to reduce the adhesion and remove biofilms of individual and mixed cultures of food pathogenic bacteria

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