Selective glucose recognition by boronic acid azoprobe/γ-cyclodextrin complexes in water

Shimpuku, Chie; Ozawa, Rimiko; Sasaki, Akira; Sato, Fuyuki; Hashimoto, Takeshi; Yamauchi, Akiyo; Suzuki, I.; Hayashita, Takashi

doi:10.1039/b819938h

Cited by 72 publications

(45 citation statements)

References 34 publications

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“…The chromophores are known to exhibit a strong induced circular dichromism (ICD) by forming an inclusion complex with CyDs based on the chiral nature of the CyD cavities. [24][25][26] Thus, the ICD spectra were examined in 40% DMSO-60% water (v/v) to clarify the types of inclusion complexes (Fig. S1, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Effects of Cyclodextrins on Intramolecular Photoinduced Electron Transfer in a Boronic Acid Fluorophore

et al. 2014

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An inclusion complex consisting of a boronic acid fluorophore (C1-APB) and β-cyclodextrin (β-CyD) acts as a supramolecular sugar sensor whose response mechanism is based on photoinduced electron transfer (PET) from the excited pyrene to the boronic acid. We have investigated the PET process in C1-APB/CyD complexes by using time-resolved photoluminescence (TRPL) measurements at room temperature, and have succeeded in estimating the electron-transfer time to be about 1 ns. We have also studied the effects of CyDs on the PET process by comparing two kinds of CyDs (α-CyD, β-CyD) under different water-dimethyisulfoxide (DMSO) concentration conditions. We found that the CyDs interacting with the boronic acid moiety completely inhibits PET quenching and increases the monomer fluorescence intensity.Keywords Sugar recognition, time-resolved photoluminescence measurements, photoinduced electron transfer, cyclodextrin

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Section: Resultsmentioning

confidence: 99%

Effects of Cyclodextrins on Intramolecular Photoinduced Electron Transfer in a Boronic Acid Fluorophore

et al. 2014

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“…This probe was water soluble and changed its color from yellow to red to orange with increasing pH. From UV-vis spectra in the presence of DA or analogous compounds, based on 1 : 1 complex formation of the probe with a guest, the highest binding constant of (1.11 0.021) 10 2 M 1 was noted for DA. At pH 8, the solution color changed from red to orange upon the addition of DA.…”

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Design and Function of Novel Azoprobe Possessing Multipoint Binding Sites for Dopamine Recognition

2012

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“…9) The phenylboronic acid azoprobe/γ-CyD complex sensor was found to show high glucose selectivity in water by forming a 2:1 inclusion complex of phenylboronic azoprobes with γ-CyD. Herein, we designed phenylboronic acid azoprobe (PBA)-modified polyamidoamine (PAMAM) dendrimer as a saccharide recognition sensor.…”

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confidence: 99%

Preparation of Saccharide Exchange Membrane Modified by Phenylboronic Acid Azoprobe/Polyamidoamine (PAMAM) Dendrimer

Tsuchido¹,

Aimu²,

Toda³

et al. 2014

J.I.E.

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Phenylboronic acid azoprobe (B-Azo-Cb) for saccharide recognition was synthesized. B-AzoCb/polyamidoamine (PAMAM) complex was synthesized by the condensation reaction of terminal carboxylic group of B-Azo-Cb and surface amine of PAMAM dendrimer. Thin porous cellulose acetate membrane embedded with B-Azo-Cb/PAMAM dendrimer complex was prepared from cellulose acetate, formamide, acetone, and B-Azo-Cb/PAMAM dendrimer complex by casting on the glass plate at various temperatures. The saccharide transportability was evaluated by measuring the amount of saccharide in receiving solution. The amount of saccharide transport of porous cellulose acetate membrane embedded with B-Azo-Cb/PAMAM dendrimer complex was higher at low temperature-treated membrane, and low pH of receiving solution. In contrast, the saccharide transportabilities through non-treated cellulose acetate membrane were the same at any pH of receiving solution. Saccharide transportability was in the order of galactose > glucose > fructose (B-Azo-Cb/PAMAM G4 modified membrane), and glucose > galactose > fructose (B-Azo-Cb/PAMAM G5 modified membrane). These orders were the same of the saccharide response in solution. These results indicated that the saccharide transport of B-AzoCb/PAMAM-embedded membrane is successfully mediated by the phenylboronic acid.

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Selective glucose recognition by boronic acid azoprobe/γ-cyclodextrin complexes in water

Abstract: The phenylboronic acid azoprobe (BA-Azo)/gamma-cyclodextrin (gamma-CD) complex exhibits a selective response for D-glucose by forming a supramolecular 2:1 inclusion complex of the azoprobes with D-glucose inside the gamma-CD cavity.

Cited by 72 publications

References 34 publications

Effects of Cyclodextrins on Intramolecular Photoinduced Electron Transfer in a Boronic Acid Fluorophore

Effects of Cyclodextrins on Intramolecular Photoinduced Electron Transfer in a Boronic Acid Fluorophore

Design and Function of Novel Azoprobe Possessing Multipoint Binding Sites for Dopamine Recognition

Preparation of Saccharide Exchange Membrane Modified by Phenylboronic Acid Azoprobe/Polyamidoamine (PAMAM) Dendrimer

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