Synthesis of gold nanoparticles bearing the Thomsen–Friedenreich disaccharide: a new multivalent presentation of an important tumor antigen

Svarovsky, Sergei; Székely, Zoltán; Barchi, Joseph J.

doi:10.1016/j.tetasy.2004.12.003

Cited by 61 publications

(39 citation statements)

References 54 publications

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“…This approach for the preparation of glyconanoparticles was introduced by PenadØs and co-workers [17,21] to present glucose, lactose, maltose, and the Lewis x trisaccharide on AuNPs. A similar approach has been taken by the groups of Russell, [24] Lin, [25] Barchi, [26] and others. Reductive amination chemistry for glyco-AuNP preparation was introduced by Kamerling and co-workers for the thiol-functionalization of unprotected glycans.…”

Section: Introductionmentioning

confidence: 95%

Chemoselective Capture of Glycans for Analysis on Gold Nanoparticles: Carbohydrate Oxime Tautomers Provide Functional Recognition by Proteins

Thygesen¹,

Sauer²,

Jensen³

2009

Chemistry A European J

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Nanoparticles functionalized with glycans are emerging as powerful solid-phase chemical tools for the study of protein-carbohydrate interactions using nanoscale properties for detection of binding events. Methods or reagents that enable the assembly of glyconanoparticles from unprotected glycans in two consecutive chemoselective steps with meaningful display of the glycan are highly desirable. Here, we describe a novel bifunctional reagent that 1) couples to glycans by oxime formation in solution, 2) aids in purification through a lipophilic trityl tag, and 3) after deprotection then couples to gold nanoparticles through a thiol. NMR studies revealed that these oximes exist as both the open-chain and N-glycosyl oxy-amine tautomers. Glycan-linker conjugates were coupled through displacement of ligands from preformed, citrate-stabilized gold nanoparticles. Recognition of these glycans by proteins was studied with a lectin, concanavalin A (ConA), in an aggregation assay and with a processing enzyme and glucoamylase (GA). We demonstrate that the presence of the N-glycosyl oxy-amines clearly enables functional recognition in sharp contrast to the corresponding reduced oxy-amines. This concept is then realized in a novel reagent, which should facilitate nanoglycobiology by enabling the operationally simple capture of glycans and their biologically meaningful display.

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Section: Introductionmentioning

confidence: 95%

Chemoselective Capture of Glycans for Analysis on Gold Nanoparticles: Carbohydrate Oxime Tautomers Provide Functional Recognition by Proteins

Thygesen¹,

Sauer²,

Jensen³

2009

Chemistry A European J

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“…52 Glyco-nanoparticles, i.e., nanoparticles with carbohydrates immobilized on the exterior, are emerging as promising tools for glycobiological studies. [53][54][55][56][57][58][59] It is known that the density of carbohydrates on a surface is crucial for their biological functions. 60,61 As a model for our glyco-nanoparticle studies, we chose to immobilize glucosamine derivative 14 because of important biological properties of glucosamine derivatives.…”

Section: Synthesis Of Carbohydrate-modified Aptesmentioning

confidence: 99%

Functionalization of magnetic nanoparticles with organic molecules: Loading level determination and evaluation of linker length effect on immobilization

Balasubramanian

Huang

2007

Chirality

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A general method is introduced to immobilize organic molecules on magnetic nanoparticles through silanization reactions and determine the maximum loading level by UV-vis spectroscopy. Loading levels of 1.5 x 10(-3) mol per gram of nanoparticle were obtained with structurally diverse compounds such as rhodamine B and glucosamine. The length of the linker did not have a significant effect on loading as comparable maximum amounts of rhodamine B were immobilized on magnetic nanoparticles regardless of the linker length. Interestingly, rhodamine B derivatives lost conjugation during synthetic manipulations due to reversible spiroisobenzofuran formation. Full regeneration of conjugation was found to be slow with rhodamine B attached on magnetic nanoparticles. The results obtained from these studies will be useful for studying surface functionalization of MNPs in general.

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“…The most popular method involves the usage of thiol terminated carbohydrates as capping ligands during formation of Au-NPs [109][110][111][112][113][114]. This method is very convenient as carbohydrates can be readily functionalized with thiols usually at the reducing end.…”

Section: Gold-np Synthesismentioning

confidence: 99%

“…Immobilization of TACAs on a polyvalent NP template represents a new strategy to raise strong immune responses in vivo. To this end, Barchi and coworkers prepared water-soluble stable Au-NPs coated with the thiol derivatized TF antigen [111]. The TF-AuNP caused aggregation of a TF specific antibody as well as the agglutination of a TF specific lectin, i.e., peanut agglutinin, but not the mannose specific lectin Pisum sativum agglutinin.…”

Section: Carbohydrate-protein and Carbohydrate-antibody Interactionsmentioning

confidence: 99%

Glyco-Nanomaterials: Translating Insights from the “Sugar-Code” to Biomedical Applications

El‐Boubbou¹,

Huang²

2011

CMC

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Over the past decade, diagnostics and therapeutics have changed gradually towards the use of more specific and targeted approaches. The most profound impact has been in the nanotechnology sectors, where an explosion in directing biomolecules to specific biomarkers has illustrated great potentials not only in detection but also in targeted therapy. Increased knowledge of the diseases at the molecular level catalyzed a shift towards identifying new biological indicators. In particular, carbohydrate-mediated molecular recognitions using nano-vehicles are likely to increasingly affect medicine opening a new area of biomedical applications. This article provides an overview of the recent progress made in recruiting the "sugar code" functionalized on various nano-platforms to decipher cellular information for both in vitro and in vivo applications. Today's glyco-technologies are enabling better detection with great therapeutic potentials. Tomorrow they are likely to bring a full understanding of the "cell-glyconanomaterial bio-conversation" where major biomedical problems will be overcome translating insights from the "glyco-nanoworld" into clinical practice.

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Synthesis of gold nanoparticles bearing the Thomsen–Friedenreich disaccharide: a new multivalent presentation of an important tumor antigen

Cited by 61 publications

References 54 publications

Chemoselective Capture of Glycans for Analysis on Gold Nanoparticles: Carbohydrate Oxime Tautomers Provide Functional Recognition by Proteins

Chemoselective Capture of Glycans for Analysis on Gold Nanoparticles: Carbohydrate Oxime Tautomers Provide Functional Recognition by Proteins

Functionalization of magnetic nanoparticles with organic molecules: Loading level determination and evaluation of linker length effect on immobilization

Glyco-Nanomaterials: Translating Insights from the “Sugar-Code” to Biomedical Applications

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Synthesis of gold nanoparticles bearing the Thomsen–Friedenreich disaccharide: a new multivalent presentation of an important tumor antigen

Cited by 61 publications

References 54 publications

Chemoselective Capture of Glycans for Analysis on Gold Nanoparticles: Carbohydrate Oxime Tautomers Provide Functional Recognition by Proteins

Chemoselective Capture of Glycans for Analysis on Gold Nanoparticles: Carbohydrate Oxime Tautomers Provide Functional Recognition by Proteins

Functionalization of magnetic nanoparticles with organic molecules: Loading level determination and evaluation of linker length effect on immobilization

Glyco-Nanomaterials: Translating Insights from the &#x201C;Sugar-Code&#x201D; to Biomedical Applications

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Glyco-Nanomaterials: Translating Insights from the “Sugar-Code” to Biomedical Applications