Sugar microarray via click chemistry: molecular recognition with lectins and amyloid β (1–42)

Matsumoto, Erino; Yamauchi, Takahiro; Fukuda, Tomohiro; Miura, Yoshiko

doi:10.1088/1468-6996/10/3/034605

Cited by 16 publications

(11 citation statements)

References 30 publications

(42 reference statements)

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“…On capturing the peptides Aβ(1-40) and Aβ(1-42), a characteristic oxidation peak was observed at 0.6 V (vs. Ag/AgCl) through differential pulse voltammetry, which was further confirmed by AFM images showing increase in roughness on the surface after capturing of peptides by the sialic acid. In another study, using circular dichroism spectroscopy and fluorescence microscopy, SAM of sialic acid and 6-sulfo-GlcNAc was found to have tendency to change the conformations of Aβ(1-42) into β-sheet while also aggregating Aβ into fibrils having a larger diameter compare to that created by SAM of β-Glc [25]. In the same work, binding affinities of different common monosaccharide SAMs to their corresponding lectins were also studied and were found to be the range of 10 -7 -10 -8 M.…”

Section: Indirect Methodsmentioning

confidence: 99%

Self-Assembled Monolayers of Carbohydrate Derivatives on Gold Surfaces

Bhattarai¹,

Neupane²,

Mikhaylov³

et al. 2017

Carbohydrate

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Self-assembled monolayers (SAMs) presenting carbohydrates (glycans) have been widely prepared on gold surfaces to mimic the carbohydrate surfaces that are involved in molecular recognition phenomena in living cells. The binding affinity of carbohydrate immbolized on SAM surfaces to various carbohydrate-binding proteins (such as lectins) can be studied by optical, electrochemical, piezoelectrical and thermal sensing techniques. The lectins present on the surface of pathogens (e.g., bacteria or viruses) can be used as targets for capturing onto carbohydrates immobilized on SAM surfaces. The immobilized carbohydrates can also be used for detecting different types of disease biomarkers present in bodily fluids. Synergistic properties of carbohydrate SAMs and gold nanoparticles can be used for vaccine preparation and drug delivery. By studying different types of glycans, their properties, and the behavior toward recognition of specific pathogens and biomarkers, we can develop not only new therapeutics but also enhance the diagnostic strategies of various diseases. In this chapter, we discuss carbohydrate-terminated SAMs and their common preparation strategies. Next, we focus on roles of different components of SAMs, characterization techniques, and applications.

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Section: Indirect Methodsmentioning

confidence: 99%

Self-Assembled Monolayers of Carbohydrate Derivatives on Gold Surfaces

Bhattarai¹,

Neupane²,

Mikhaylov³

et al. 2017

Carbohydrate

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“…31,32 This reagent has a terminal alkyne group, and is shown in Fig. S2 in the Supporting Information.…”

Section: Surface Chemistrymentioning

confidence: 99%

“…For click chemistry, a freshly prepared solution containing 2 mM CuSO4, 40 mM sodium ascorbate, 5% glycerol in ultrapure water was used, 32 which reacts with 6-azidohexyl-lactose. For coupling of the 6-aminohexyl-lactose to the DAPEG-NHS surface, a disodium hydrogenphosphate buffer (0.5 M, pH 8.5) was used.…”

Section: Microspotting Of Lactose Moieties and Flow-cell Assemblingmentioning

confidence: 99%

A Glyco-chip for the Detection of Ricin by an Automated Chemiluminescence Read-out System

et al. 2013

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The plant toxin ricin is a lectin that binds to D-galactose or lactose moieties by multivalent interactions. In the present work, this avidity was used to develop a novel sandwich glyco-immunoassay using a carbohydrate microarray. For realization, 6-azidohexyl-lactose was immobilized on an alkyne silane surface by Cu(I) catalyzed click chemistry. This procedure is fast, and prevents any nonspecific binding on the microarray surface. Ricin binds via its B-chain to the lactose moieties, and is detected by the biotinylated anti-ricin A-chain. By adding a horseradish peroxidase-labeled streptavidin, a chemiluminescence signal can be generated. This method is described as a sandwich-type glyco-immunoassay. The signal on the glyco-chip can be regenerated for at least 10 measurements. The limit of detection was estimated to be 80 ng mL -1 . The assay was carried out on the automated microarray readout platform MCR 3. In this way, it took 20 min for one measurement, including regeneration of the chip surface.

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“…Acetylene-terminated disulfide and azide-terminated a-Man were synthesized according to the literature. 16,17 Characterization 1 H (300MHz) and 13 C (75 MHz) nuclear magnetic resonance spectra were recorded in CDCl 3 and D 2 O using a Varian Gemini 300 spectrometer (Varian, Palo Alto, CA, USA) equipped with a Sun workstation. Gel permeation chromatography was carried out with a JASCO 800 high-performance liquid chromatographer (JASCO, Tokyo, Japan) with Shodex SB803 HQ columns (Showa Denko K. K., Tokyo, Japan) and phosphate-buffered saline as the eluent.…”

Section: Experimental Procedures Materialsmentioning

confidence: 99%

Biological specific recognition of glycopolymer- modified interfaces by RAFT living radical polymerization

Toyoshima

Oura

Fukuda

et al. 2009

Polym J

Self Cite

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Glycopolymers with a-galactose (a-Gal) and a-mannose (a-Man) were synthesized by means of living radical polymerization with a reversible addition-fragment chain transfer reagent, and the thin-layer formation of glycopolymers was investigated in terms of protein recognition abilities. Thiol-terminated glycopolymers formed a thin layer of about 2.5 nm in thickness on a gold substrate, and the glycopolymer thin layer showed specific interaction with sugar recognition proteins (lectins and Shiga toxins (Stxs)). The interactions were highly specific, and the signal-to-noise ratio of protein recognition was greater than 16. Glycopolymer-substituted gold nanoparticles (GNPs) also showed biorecognition abilities and protein-specific aggregation. The protein recognition abilities of the GNPs were also analyzed. The glycopolymer-substituted GNPs were utilized for signal amplification of surface plasmon resonance (SPR) to detect protein-saccharide recognition. The glycopolymer with a-Gal showed a strong interaction with Stxs according to SPR measurements, suggesting a possible application of a-Gal-substituted GNPs in Stx-1 biosensing.

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Sugar microarray via click chemistry: molecular recognition with lectins and amyloid β (1–42)

Cited by 16 publications

References 30 publications

Self-Assembled Monolayers of Carbohydrate Derivatives on Gold Surfaces

Self-Assembled Monolayers of Carbohydrate Derivatives on Gold Surfaces

A Glyco-chip for the Detection of Ricin by an Automated Chemiluminescence Read-out System

Biological specific recognition of glycopolymer- modified interfaces by RAFT living radical polymerization

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