Multivalent glycosylated nanoparticles for studying carbohydrate–protein interactions

Adak, Asok; Lin, Hong-Jyune; Lin, Chun‐Cheng

doi:10.1039/c4ob00827h

Cited by 54 publications

(39 citation statements)

References 89 publications

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“…A variety of glyconanomaterials have been developed, such as carbohydrate-coated gold nanoparticles, carbon nanomaterials, quantum dots, silica nanoparticles, etc., and have found utilities in for example biosensing, imaging and therapeutics. [2][3][4][5][6][7][8][9][10] The binding affinity of the glyconanomaterials with their receptors is the most important feature that dictates the performance of the glyconanomaterials in these applications. In order to calculate the affinity constant, the carbohydrate density on the nanomaterials must be determined.…”

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confidence: 99%

Quantitative Fluorine NMR To Determine Carbohydrate Density on Glyconanomaterials Synthesized from Perfluorophenyl Azide-Functionalized Silica Nanoparticles by Click Reaction

et al. 2015

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A quantitative fluorine NMR ((19)F qNMR) method was developed to determine the carbohydrate density on glyconanomaterials. Mannose (Man)- and galactose (Gal)-conjugated silica nanoparticles (SNPs) were synthesized from perfluorophenyl azide (PFPA)-functionalized SNPs and propargylated Man or Gal by copper-catalyzed azide-alkyne cycloaddition (click reaction). After treating PFPA-SNPs or Man-SNPs with hydrofluoric acid followed by lyophilization, the remaining residues were directly subjected to (19)F NMR analysis. The density of PFPA on PFPA-SNP was determined to be 7.7 ± 0.2 × 10(-16) nmol/nm(2) and Man on Man-SNP to be 6.4 ± 0.2 × 10(-16) nmol/nm(2) giving a yield of ∼83% for the click coupling reaction. The apparent dissociation constant (Kd) of Man-SNPs with fluorescein isothiocyanate (FITC)-concanavalin A (Con A) was determined using a fluorescence competition assay to be 0.289 ± 0.003 μM, which represents more than 3 orders of magnitude affinity increase compared to free Man with Con A.

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Quantitative Fluorine NMR To Determine Carbohydrate Density on Glyconanomaterials Synthesized from Perfluorophenyl Azide-Functionalized Silica Nanoparticles by Click Reaction

et al. 2015

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“…[18][19][20] Glyconanoparticles can be specifically tailored to allow for the bioanalytical detection of various biological targets. [21][22][23] Detection of such targets can be achieved by varying several properties of the carbohydratefunctionalised nanoparticles viz. : 1) the material used to create the nanocore and the methodology applied to assemble the carbohydrate on the nanoparticle surface; 2) the carbohydrate ligand itself; 3) the length of the anchor chain tethering the carbohydrate to the nanoparticle surface; and 4) the density of carbohydrate molecules on the nanoparticle surface.…”

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confidence: 99%

Glyconanoparticles for colorimetric bioassays

Marín

Schofield

Field

et al. 2015

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Carbohydrate molecules are involved in many of the cellular processes that are important for life. By combining the specific analyte targeting of carbohydrates with the multivalent structure and change of solution colour as a consequence of plasmonic interactions with the aggregation of metal nanoparticles, glyconanoparticles have been used extensively for the development of bioanalytical assays. The noble metals used to create the nanocore, the methodologies used to assemble the carbohydrates on the nanoparticle surface, the carbohydrate chosen for each specific target, the length of the tether that separates the carbohydrate from the nanocore and the density of carbohydrates on the surface all impact on the structural formation of metal based glyconanoparticles. This tutorial review highlights these key components, which directly impact on the selectivity and sensitivity of the developed bioassay, for the colorimetric detection of lectins, toxins and viruses.3

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“…To analyze the carbohydrate-protein interactions quantitatively, various glyconanoparticle systems bearing different carbohydrate epitopes have been described for the investigation of specific binding interactions through several methods. [18] These methods include surface plasmon resonance (SPR), [19] quartz crystal microbalance (QCM) techniques, [20] isothermal titration calorimetry (ITC), [21] magnetic resonance imaging (MRI), [22] fluorescence measurements, [23] and dynamic light scattering (DLS). [24] We previously reported that glyco-AuNPs can be used for labeling specific proteins on the cell surface through carbohydrate-receptor interactions.…”

Section: Introductionmentioning

confidence: 99%

Fabrication of Highly Stable Glyco‐Gold Nanoparticles and Development of a Glyco‐Gold Nanoparticle‐Based Oriented Immobilized Antibody Microarray for Lectin (GOAL) Assay

Huang

Adak

et al. 2015

Chemistry A European J

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The design of high-affinity lectin ligands is critical for enhancing the inherently weak binding affinities of monomeric carbohydrates to their binding proteins. Glyco-gold nanoparticles (glyco-AuNPs) are promising multivalent glycan displays that can confer significantly improved functional affinity of glyco-AuNPs to proteins. Here, AuNPs are functionalized with several different carbohydrates to profile lectin affinities. We demonstrate that AuNPs functionalized with mixed thiolated ligands comprising glycan (70 mol %) and an amphiphilic linker (30 mol %) provide long-term stability in solutions containing high concentrations of salts and proteins, with no evidence of nonspecific protein adsorption. These highly stable glyco-AuNPs enable the detection of model plant lectins such as Concanavalin A, wheat germ agglutinin, and Ricinus communis Agglutinin 120, at subnanomolar and low picomolar levels through UV/Vis spectrophotometry and dynamic light scattering, respectively. Moreover, we develop in situ glyco-AuNPs-based agglutination on an oriented immobilized antibody microarray, which permits highly sensitive lectin sensing with the naked eye. In addition, this microarray is capable of detecting lectins presented individually, in other environmental settings, or in a mixture of samples. These results indicate that glyconanoparticles represent a versatile and highly sensitive method for detecting and probing the binding of glycan to proteins, with significant implications for the construction of a variety of platforms for the development of glyconanoparticle-based biosensors.

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Multivalent glycosylated nanoparticles for studying carbohydrate–protein interactions

Cited by 54 publications

References 89 publications

Quantitative Fluorine NMR To Determine Carbohydrate Density on Glyconanomaterials Synthesized from Perfluorophenyl Azide-Functionalized Silica Nanoparticles by Click Reaction

Quantitative Fluorine NMR To Determine Carbohydrate Density on Glyconanomaterials Synthesized from Perfluorophenyl Azide-Functionalized Silica Nanoparticles by Click Reaction

Glyconanoparticles for colorimetric bioassays

Fabrication of Highly Stable Glyco‐Gold Nanoparticles and Development of a Glyco‐Gold Nanoparticle‐Based Oriented Immobilized Antibody Microarray for Lectin (GOAL) Assay

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