Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

Martínez, Álvaro; Mellet, Carmen Ortiz; Fernández, José Manuel Garcı́a

doi:10.1039/c2cs35424a

Cited by 231 publications

(143 citation statements)

References 180 publications

(319 reference statements)

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“…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. Furthermore, the trimeric thiosugar cluster backbone would be expected to be relatively flexible and, in addition, its peripheral thiomannosyl moieties held much further away from the ND surface than the mannosyl units featured in the 1 st -generation NDs.…”

Section: Introductionmentioning

confidence: 99%

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: 99%

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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“…It is also known that glucose-based surfaces/compounds can display different wetability properties. Cyclodextrins, for instance, are water-soluble compounds with a hydrophobic cavity 40 , as the orientation of the C-OH groups in glucose identifies regions of different water-loving properties 41 . A striking example is constituted by two allomorphs of cellulose, Iα and Iβ, the (100) surfaces of which are, respectively, hydrophilic and hydrophobic 41 .…”

Section: Understanding the Origin Of Biocidal Effect Of Slmentioning

confidence: 99%

Biocidal Properties of a Glycosylated Surface: Sophorolipids on Au(111)

Valotteau

Calers

Casale

et al. 2015

ACS Appl. Mater. Interfaces

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Classical antibacterial surfaces usually involve antiadhesive and/or biocidal strategies. Glycosylated surfaces are usually used to prevent biofilm formation via antiadhesive mechanisms. We report here the first example of a glycosylated surface with biocidal properties created by the covalent grafting of sophorolipids (a sophorose unit linked by a glycosidic bond to an oleic acid) through a self-assembled monolayer (SAM) of short aminothiols on gold (111) surfaces. The biocidal effect of such surfaces on Gram+ bacteria was assessed by a wide combination of techniques including microscopy observations, fluorescent staining and bacterial growth tests. About 50% of the bacteria are killed via alteration of the cell envelope. In addition, the role of the sophorose unit and aliphatic chain configuration are highlighted by the lack of activity of substrates modified respectively with sophorose-free oleic acid and sophorolipid-derivative having a saturated aliphatic chain. This system 2 demonstrates thus the direct implication of a carbohydrate in the destabilization and disruption of the bacterial cell envelope.3

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“…37 Moreover, the thiourea-forming reaction has been proven to be extremely useful in ''click-type'' multiconjugation schemes. 38,39 The pDNA complexing capabilities and transfection efficiencies of 2-4 have been evaluated in comparison with paCD 1, one of the most efficient cyclodextrin-based vector candidates reported to date. 33 For the preparation of the differently-substituted pGaCDs 2-4 a convergent synthetic scheme was designed in which the key step is the coupling reaction of the heptaisothiocyanate 17 33 with a complementary amine-armed glycoconjugate (Scheme 1).…”

Section: Design Criteria and Synthesismentioning

confidence: 99%

Cyclodextrin-scaffolded amphiphilic aminoglucoside clusters: self-assembling and gene delivery capabilities

et al. 2014

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Precise control over the architecture of gene carriers is instrumental to manipulate gene delivery efficiency.Combining cationic centers and carbohydrate motifs into monodisperse architectures has been proposed as a suitable strategy to impart nucleic acid condensation abilities while preserving biocompatibility. Herein, we have assessed the influence of the arrangement and orientation of cationic elements on the self-assembling and gene transfer capabilities of polycationic glycoamphiphilic cyclodextrins (pGaCDs). For such purposes, a series of cyclodextrin multiconjugates bearing aminoglucoside motifs at their primary rim and hexanoyl chains at the secondary positions were synthesized. In the presence of pDNA, pGaCDs self-assemble into nanoaggregates that promote cellular uptake and gene expression in COS-7 cells with efficiencies that are intimately associated with the arrangement of amino functionalities imposed by the aminoglucoside antennae onto the cyclodextrin-scaffolded cluster. Although transfection efficiencies were lower than those observed for polyethyleneimine (PEI)-based polyplexes and previously-reported polycationic amphiphilic cyclodextrins (paCDs), the results reported herein illustrate (i) the dramatic influence that subtle architectural modifications exert on the supramolecular organization of pGaCDs and (ii) the virtues of monodisperse systems for tailoring gene transfer capabilities.

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Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

Cited by 231 publications

References 180 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

Biocidal Properties of a Glycosylated Surface: Sophorolipids on Au(111)

Cyclodextrin-scaffolded amphiphilic aminoglucoside clusters: self-assembling and gene delivery capabilities

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