Inhibition of Adhesion of Type 1 Fimbriated Escherichia coli to Highly Mannosylated Ligands

Nagahori, Noriko; Lee, Reiko T.; Nishimura, Shin‐Ichiro; Pagé, Daniel; Roy, René; Lee, Yuan C.

doi:10.1002/1439-7633(20020902)3:9<836::aid-cbic836>3.0.co;2-2

Cited by 154 publications

(107 citation statements)

References 23 publications

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“…Indeed various O-glycoside-derived trimeric clusters have been shown to be strong ligands for FimH compared with their corresponding monovalent analogues. 20,28 Moreover, it has been demonstrated that trimeric mannoside and thiomannoside clusters, related to those proposed, often give relatively large multivalent effects towards mannose-specific lectins. [56][57][58][59][60] The sugar-linker of our 2 nd -generation ND-sugar conjugates is quite different from the one featured in the 1 st -generation NDs, (synthesized through the "clicking" of propargyl glycosides to ND-grafted azido functions) and would thus very probably make different secondary interactions with the sugar-binding pocket in FimH.…”

Section: Introductionmentioning

confidence: 80%

Inhibition of type 1 fimbriae-mediated Escherichia coli adhesion and biofilm formation by trimeric cluster thiomannosides conjugated to diamond nanoparticles

et al. 2015

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Inhibition of type 1 fi mbriae-mediated Escherichia coli adhesion and biofi lm formation by trimeric cluster thiomannosides conjugated to diamond nanoparticles Trimeric thiosugar clusters, conveniently obtained through a thiol-ene "click" strategy, have been effi ciently conjugated to alkynyl-functionalized nanodiamonds (NDs) using a Cu(I)-catalysed "click" reaction. These tri-thiomannoside clusterconjugated NDs (ND-Man 3 ) are shown to be potent inhibitors of type 1 fi mbriae-mediated E. coli adhesion to yeast and T24 bladder cells and moreover to inhibit E. coli-mediated biofi lm formation. This latter feature has only rarely been reported in the past for analogues featuring such simple multivalent glycosidic motifs and would constitute a useful additional characteristic of any anti-adhesive drug lead. anti-adhesive nanoparticles displaying activity against biofilms. In this work, trimeric thiomannoside clusters conjugated to nanodiamond particles (ND) were targeted for investigation. NDs have attracted attention as a biocompatible nanomaterial and we were curious to see whether the high mannose glycotope density obtained upon grouping monosaccharide units in triads might lead to the corresponding NDconjugates behaving as effective inhibitors of E. coli type 1 fimbriae-mediated adhesion as well as of biofilm formation. The required trimeric thiosugar clusters were obtained through a convenient thiol-ene "click" strategy and were subsequently conjugated to alkynyl-functionalized NDs using a Cu(I)-catalysed "click" reaction. We demonstrated that the tri-thiomannoside cluster-conjugated NDs (ND-Man 3 ) show potent inhibition of type 1 fimbriae-mediated E. coli adhesion to yeast and T24 bladder cells as well as of biofilm formation. The biofilm disrupting effects demonstrated here have only rarely been reported in the past for analogues featuring such simple glycosidic motifs. Moreover, the finding that the tri-thiomannoside cluster (Man 3 N 3 ) is itself a relatively efficient inhibitor, even when not conjugated to any ND edifice, suggests that alternative mono-or multivalent sugar-derived analogues might also be usefully explored for E. coli-mediated biofilm disrupting properties.

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Section: Introductionmentioning

confidence: 80%

Inhibition of type 1 fimbriae-mediated Escherichia coli adhesion and biofilm formation by trimeric cluster thiomannosides conjugated to diamond nanoparticles

et al. 2015

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“…After adhesion, bacteria may form fully developed biofilms that are resistant to treatment because of decreased efficacy of available antibiotics. One widely explored alternative to conventional antibiotics is thus the development of antiadhesive agents based on soluble competitors for the ligands that bacteria bind to during the initial stages of reversible adhesion in our bodies (2,7,13,22). It is typically thought that bodily fluid flow will reduce bacterial adhesion (5,30,35), presuming that specific receptor-ligand-mediated adhesion always occurs through slip bonds whose adhesive strength is exponentially reduced by force (1).…”

mentioning

confidence: 99%

Elevated Shear Stress Protects Escherichia coli Cells Adhering to Surfaces via Catch Bonds from Detachment by Soluble Inhibitors

Nilsson

Thomas²,

Sokurenko

et al. 2006

Appl Environ Microbiol

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Soluble inhibitors find widespread applications as therapeutic drugs to reduce the ability of eukaryotic cells, bacteria, or viruses to adhere to surfaces and host tissues. Mechanical forces resulting from fluid flow are often present under in vivo conditions, and it is commonly presumed that fluid flow will further add to the inhibitive effect seen under static conditions. In striking contrast, we discover that when surface adhesion is mediated by catch bonds, whose bond life increases with increased applied force, shear stress may dramatically increase the ability of bacteria to withstand detachment by soluble competitive inhibitors. This shear stress-induced protection against inhibitor-mediated detachment is shown here for the fimbrial FimH-mannose-mediated surface adhesion of Escherichia coli. Shear stress-enhanced reduction of bacterial detachment has major physiological and therapeutic implications and needs to be considered when developing and screening drugs.

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“…Figure 14 illustrates typical cases wherein L-lysine (Nagahori et al, 2002) was used as scaffold (33, 37, 38), together with "Majoral-type" cyclotriphosphazene (34) (Touaibia, Roy, 2008), and aromatic scaffolds that included hexaphenylbenzene (35) (Chabre et al, 2011) and hexamethylthiobenzene (36) .…”

Section: Glycodendrimers As Bacterial Anti-adhesinsmentioning

confidence: 99%

Glycodendrimers: versatile tools for nanotechnology

Roy

Shiao

Rittenhouse-Olson

2013

Braz. J. Pharm. Sci.

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Combining nanotechnology with glycobiology has triggered an exponential growth of research activities in the design of novel functional bionanomaterials (glyconanotechnology). More specifically, recent synthetic advances towards the tailored and versatile design of glycosylated nanoparticles namely glyconanoparticles, considered as synthetic mimetics of natural glycoconjugates, paved the way toward diverse biomedical applications. The accessibility of a wide variety of these structured nanosystems, in terms of shapes, sizes, and organized around stable nanoparticles have readily contributed to their development and applications in nanomedicine. In this context, glycosylated gold-nanoparticles (GNPs), glycosylated quantum dots (QDs), fullerenes, single-wall natotubes (SWNTs), and self-assembled glycononanoparticles using amphiphilic glycopolymers or glycodendrimers have received considerable attention to afford powerful imaging, therapeutic, and biodiagnostic devices. This review will provide an overview of the most recent syntheses and applications of glycodendrimers in glycoscience that have permitted to deepen our understanding of multivalent carbohydrate-protein interactions. Together with synthetic breast cancer vaccines, inhibitors of bacterial adhesions to host tissues including sensitive detection devices, these novel bionanomaterials are finding extensive relevance.

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Inhibition of Adhesion of Type 1 Fimbriated Escherichia coli to Highly Mannosylated Ligands

Cited by 154 publications

References 23 publications

Inhibition of type 1 fimbriae-mediated Escherichia coli adhesion and biofilm formation by trimeric cluster thiomannosides conjugated to diamond nanoparticles

Inhibition of type 1 fimbriae-mediated Escherichia coli adhesion and biofilm formation by trimeric cluster thiomannosides conjugated to diamond nanoparticles

Elevated Shear Stress Protects Escherichia coli Cells Adhering to Surfaces via Catch Bonds from Detachment by Soluble Inhibitors

Glycodendrimers: versatile tools for nanotechnology

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