Selective adsorption of carbohydrates and glycoproteins via molecularly imprinted hydrogels: application to visible detection by a boronic acid monomer

Kubo, Takuya; Furuta, Hayato; Naito, Toyohiro; Sano, Tomoharu; Otsuka, Koji

doi:10.1039/c7cc02310c

Cited by 18 publications

(19 citation statements)

References 44 publications

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“…All azoBs were synthesized by diazo-coupling reactions between the corresponding amine precursor compounds and phenylboronic acid derivatives (see the Experimental Section and Scheme S1 in the Supporting Information). The synthesized products were confirmed by 1 H and 13 C NMR (Figures S1 and S2, respectively), ESI-MS, and elemental analysis. Some of the azoBs were characterized using high-resolution mass spectroscopy instead of elemental analysis.…”

Section: ■ Results and Discussionmentioning

confidence: 91%

“…Electrospray ionization mass spectra (ESI-MS) were recorded by using a JEOL Accu-TOF JMS T100-CS. 1 H, 13 C, and 11 B NMR spectra were measured at 25 °C with a Bruker Avance 400 spectrometer. Elemental analyses for C, H, and N atoms were performed on a Perkin Elmer series II CHNS/ O Analyzer 2400.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…In particular, Egawa et al reported oazophenylboronic acids (azoBs) with excellent features for the colorimetric detection of sugars, one of which shows a color change from red (λ max = 521 nm) to yellow (λ max = 398 nm) in response to D-fructose. 9,10 Some azoB-based applications have already been established, such as dyemodified polymers, 11,12 imprinted hydrogels, 13 alization of Au superparticles. 14 In these reports, the drastic color change upon reaction with D-fructose was attributed to the direct N−B dative bond between the β-N atom of the azo group (Chart 1) and the boron center of boronic acid.…”

Section: ■ Introductionmentioning

confidence: 99%

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o-Azophenylboronic Acid-Based Colorimetric Sensors for d-Fructose: o-Azophenylboronic Acids with Inserted Protic Solvent Are the Key Species for a Large Color Change

et al. 2020

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Many boronic acid-based chemosensors for saccharides have been developed; however, their detection mechanisms have seldom been studied. In this study, we synthesized 10 o-azophenylboronic acid derivatives (azoBs) and conducted a fundamental study on the reactivity and the sensing mechanism of azoBs, which undergoes a large color change, e.g., from red to yellow, upon a reaction with saccharides. Their pH-independent formation constants were determined by spectrophotometric titration and then converted to the conditional formation constant K′ at pH 7.4. A linear free energy relationship was established between log K′ and the pK a of azoB. 11B NMR measurements indicate that in aprotic solvents, azoB forms a trigonal planar structure, while in protic solvents, it forms a quasi-tetrahedral structure (azoB-ROH) with a protic solvent molecule (ROH) inserted between the boronic acid moiety and the azo group. In addition, UV–vis spectroscopic studies showed that the color change during the reaction between azoB and d-fructose in ROH was caused by the release of the ROH from azoB-ROH by d-fructose. Based on the findings in this study, we proposed a guideline for designing an azoB-based chemosensor that exhibits high reactivity toward saccharides and a sufficient color change to allow for the visual detection of saccharides.

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Section: ■ Results and Discussionmentioning

confidence: 91%

Section: ■ Conclusionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

o-Azophenylboronic Acid-Based Colorimetric Sensors for d-Fructose: o-Azophenylboronic Acids with Inserted Protic Solvent Are the Key Species for a Large Color Change

et al. 2020

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“…Their results also showed that the composition and ratio of imprinted polymers affected the quality of glycoprotein imprinting, and that HRP‐imprinted silica nanomaterials could recognize HRP from spiked human serum. Kubo et al developed the PEG‐based molecularly imprinted hydrogels (MIHs) with VPBA as functional monomer and HRP, fetuin and ribonuclease B (RNase B) as templates . Moreover, they originally prepared a functional monomer that was inclusive of an azo group and aromatic boronic acid (denoted as VAAB) for fabricating fructose‐MIHs.…”

Section: Nanomaterials In Glycoproteomicsmentioning

confidence: 99%

Nanomaterials in Proteomics

Sun

Shen

et al. 2019

Adv Funct Materials

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For a deep understanding of the human proteome, the first crucial step is always the effective separation of targeted proteins/peptides from complex samples. In mass spectrometry‐based proteomics, nanomaterials have emerged as a highly effective means to separate targeted proteins/peptides and increase their relative abundance, which is beneficial to conduct mass spectrometric analysis. In particular, nanomaterials with different specific functionalities have received great attention in ordinary proteomics, phosphoproteomics, and glycoproteomics, for which the easily recognizable characteristics of these proteomes take the primary responsibility, such as the hydrophobicity, phosphate groups, cis–diol structure, and hydrophilicity. This review mainly focuses on the recent design and preparation of nanomaterials with specific recognition ability, as well as their application in the aforementioned three types of proteomics.

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“…[10][11][12][13] Zhai et al reported electrochemical imprinted sensors for the determination of ascorbic acid. Nanofiber membranes of cellulose acetate/ multi-walled carbon nanotubes/polyvinylpyrrolidone were prepared by an electrospinning technique.…”

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confidence: 99%

Molecularly Imprinted Materials in Analytical Chemistry

Kubo

2017

ANAL. SCI.

Self Cite

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A highly organized molecularly imprinted polymer (MIP) (Fig. 1) provides amazing selective molecular-recognition ability, which is an imitation of natural enzymes and antibodies. Many researchers have challenged themselves to make artificial molecular recognition materials for the selective separation and/or detection of targeting compounds in environmental or biological samples. Since Mosbach and co-wokers launched the present concept of MIP, we have created a variety of intelligent materials. 1-3Mainly, MIP-based materials are utilized for selective adsorption in solid-phase extraction (SPE). 4,5 Li et al. reported MIP with mesoporous siliceous materials modified by betainebased deep eutectic solvents. Six materials were employed as SPE adsorbents for the rapid purification of levofloxacin. 6 Thus, MIP showed highly-selective recovery (95.2%) for levofloxacin from green bean extract, and could remove interference effectively.As another trend in MIPs, core-shell-type nanoparticles have been widely used with several modification techniques.7 Zhang et al. described surface MIP for the selective recognition of pneumocandin B0 (PNB0). Methacrylic acid MAA was first grafted onto silica-gel particles in the manner of "grafting from" by using 3-methacryloxypropyl trimethoxysilane as an intermedium, and then PNB0 molecules were imprinted on the surface of the obtained particles in the presence of ethylene glycol diglycidyl ether as a cross-linker. 8 The hybrid particle showed relatively quick adsorption kinetics and decent recognition affinity toward the template over its structurally related compounds. Feng et al. indicated novel magnetic imprinted composites through a facile method using a sulfadimethoxines template. 9The inorganic magnetic nanoparticles were linked with the organic MIP through an irreversibly covalent bond. By adopting the magnetic MIP composites as extraction material, an off-line magnetic SPE/ HPLC method was established.Another significant application of MIPs is sensor technology by electrochemical and fluorescence detections. [10][11][12][13] Zhai et al. reported electrochemical imprinted sensors for the determination of ascorbic acid. Nanofiber membranes of cellulose acetate/ multi-walled carbon nanotubes/polyvinylpyrrolidone were prepared by an electrospinning technique.14 Hu et al. reported an ion imprinted polymer by using Pb(II) as a template, and applied it to prepare a lead ion-selective voltammetric sensor for Pb(II) adsorption and trace detection.15 Then, the MIP exhibited a favorable selectivity for Pb(II), compared with other heavy metal ions of Hg(II), Cd(II), Cu(II), and a negligible adsorption to other cations. Zhou et al. prepared a quantum dot-based MIP, and successfully utilized it as a fluorescent probe for highly selective and sensitive detection of carbofuran in water samples. 17 First, BHb MIPs were successfully synthesized with magnetic Fe3O4@Au nanoparticles as a carrier by surface modification of mercapto propionic acid for introducing carboxyl groups, combined with dopam...

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Selective adsorption of carbohydrates and glycoproteins via molecularly imprinted hydrogels: application to visible detection by a boronic acid monomer

Cited by 18 publications

References 44 publications

o-Azophenylboronic Acid-Based Colorimetric Sensors for d-Fructose: o-Azophenylboronic Acids with Inserted Protic Solvent Are the Key Species for a Large Color Change

o-Azophenylboronic Acid-Based Colorimetric Sensors for d-Fructose: o-Azophenylboronic Acids with Inserted Protic Solvent Are the Key Species for a Large Color Change

Nanomaterials in Proteomics

Molecularly Imprinted Materials in Analytical Chemistry

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