Clusters of ligands on dendrimer surfaces

Schlick, Kristian H.; Morgan, Joel R.; Weiel, Julianna J; Kelsey, Melissa S.; Cloninger, Mary J.

doi:10.1016/j.bmcl.2011.03.100

Cited by 19 publications

(15 citation statements)

References 48 publications

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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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“…The carboxylic acid group in 2 was activated by conversion to the corresponding N -hydroxysuccinimide (NHS) ester and the product was treated with boron trifluoride diethyl etherate to produce BODIPY/KFL 3 in 30% yield for the three steps. The synthesis of the PGD with a bifunctional core began with Fmoc-Lys(Boc)-OH which was reacted with amine 4 41 under standard peptide coupling conditions. The product trialkyne 5 , obtained in 92% yield was coupled with azide-cored PGD 6 42 using copper-catalyzed 1,3-dipolar cycloaddition 43 .…”

Section: Resultsmentioning

confidence: 99%

A dendritic single-molecule fluorescent probe that is monovalent, photostable and minimally blinking

et al. 2013

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Single-molecule fluorescence techniques have emerged as a powerful approach to understand complex biological systems. However, a challenge researchers still face is the limited photostability of nearly all organic fluorophores, including the cyanine and Alexa dyes. We report a new, monovalent probe that emits in the far-red region of the visible spectrum with properties desirable for single-molecule optical imaging. This probe is based on a ring-fused boron-dipyrromethene (BODIPY) core that is conjugated to a polyglycerol dendrimer (PGD). The dendrimer makes the hydrophobic fluorophore water-soluble. This probe exhibits excellent brightness, with an emission maximum of 705 nm. We observed strikingly long and stable emission from individual PGD-BODIPY probes even in the absence of anti-fading agents such as Trolox, a combined oxidizing-reducing agent often used in single-molecule studies for improving the photostability of common imaging probes. These interesting properties greatly simplify use of the fluorophore.

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“…Other large decorations that were enabled by click chemistry include peptides [32,130,131,132,133,134], carbohydrates [104,135,136,137,138,139,140,141,142,143,144], DNA [140,145,146], sRNA [147] and chelated gadolinium [131,134]. In that area, Cloninger et al ., proposed a new way to envision surface functionalization of a dendrimer using CuAAC [148]. Departing from the conventional idea of uniformly capping end groups, they proposed to actively seek a clustering of a given decorating moieties.…”

Section: Structural Advancesmentioning

confidence: 99%

Recent Advances in Click Chemistry Applied to Dendrimer Synthesis

2015

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Dendrimers are monodisperse polymers grown in a fractal manner from a central point. They are poised to become the cornerstone of nanoscale devices in several fields, ranging from biomedicine to light-harvesting. Technical difficulties in obtaining these molecules has slowed their transfer from academia to industry. In 2001, the arrival of the "click chemistry" concept gave the field a major boost. The flagship reaction, a modified Hüisgen cycloaddition, allowed researchers greater freedom in designing and building dendrimers. In the last five years, advances in click chemistry saw a wider use of other click reactions and a notable increase in the complexity of the reported structures. This review covers key developments in the click chemistry field applied to dendrimer synthesis from 2010 to 2015. Even though this is an expert review, basic notions and references have been included to help newcomers to the field.

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Clusters of ligands on dendrimer surfaces

Cited by 19 publications

References 48 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

A dendritic single-molecule fluorescent probe that is monovalent, photostable and minimally blinking

Recent Advances in Click Chemistry Applied to Dendrimer Synthesis

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