Fluorescent chemosensors of carbohydrates. A means of chemically communicating the binding of polyols in water based on chelation-enhanced quenching

Yoon, Juyoung; Czarnik, Anthony W.

doi:10.1021/ja00040a067

Cited by 471 publications

(258 citation statements)

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“…4 Czarnik et al synthesized a boronic acid-introduced anthracence derivative, and applied to the fluorometric sensing of saccharides. 5 Shinkai et al designed and synthesized several compounds containing a boronic acid moiety, and used them as a fluorescent sensor based on a photoinduced electron-transfer effect. 6 Shinkai et al also designed a boronic acid derivative, which contains two boronic acid moieties at suitable positions, and achieved monosaccharide sensing in circular-dichroism measurements.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Interactions between Monosaccharides and a Stationary Phase Modified with Alkylboronic Acid by Means of a Liquid-Chromatographic Method

2002

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Section: Introductionmentioning

confidence: 99%

Evaluation of Interactions between Monosaccharides and a Stationary Phase Modified with Alkylboronic Acid by Means of a Liquid-Chromatographic Method

2002

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“…Although chemosensors based on boronic acid are not as selective as enzyme-based sensors, they have attracted much attention because of their greater stabilities. 4,5 Phenylboronic acid can readily form stable cyclic esters with the diol moiety of sugars in water, 6 and various types of boronic acid chemosensors with response mechanisms based on internal charge transfer (ICT), [7][8][9][10] photoinduced electron transfer (PET), [11][12][13] and fluorescent resonance energy transfer (FRET) 14 have been developed. The versatile designs of chemosensors based on supramolecular chemistry are another approach to construct novel sugar sensors.…”

Section: Introductionmentioning

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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“…Although chemosensors based on boronic acid are not as selective, they have attracted much attention because of their greater stability. 2,3 Phenylboronic acid can readily form stable cyclic esters with the diol moiety of sugars in water, 4 and various types of the boronic acid chemosensors with response mechanism based on internal charge transfer (ICT), [5][6][7][8] photoinduced electron transfer (PET), [9][10][11] and fluorescent resonance energy transfer (FRET) 12 have been developed. The versatile designs of chemosensors based on supramolecular chemistry are another approach to construct novel sugar sensors.…”

Section: Introductionmentioning

confidence: 99%

Effect of Cyclodextrins on Saccharide Sensing Function of a Fluorescent Phenylboronic Acid in Water

et al. 2008

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Sugars are essential biological molecules that play fundamental roles in metabolism and the maintenance of cell structure. They are also related to cell differentiation and immunity.1 Because of their important properties, researchers need simple methods that can quickly recognize sugars in aqueous solution. Enzymebased sensors are highly selective, but of limited use for continuous monitoring and in vivo analysis because of their poor stability and because they consume their substrate in the recognition process. Although chemosensors based on boronic acid are not as selective, they have attracted much attention because of their greater stability. 2,3 Phenylboronic acid can readily form stable cyclic esters with the diol moiety of sugars in water, 4 and various types of the boronic acid chemosensors with response mechanism based on internal charge transfer (ICT), 5-8 photoinduced electron transfer (PET), 9-11 and fluorescent resonance energy transfer (FRET) 12 have been developed. The versatile designs of chemosensors based on supramolecular chemistry are another approach to construct novel sugar sensors. [13][14][15] We reported that the complex consisting of the boronic acid fluorophore (C4-CPB) and β-cyclodextrin (β-CD) acts as a supramolecular saccharide sensor (Fig. 1). 16 The β-CD solubilizes the water-insoluble C4-CPB by forming an inclusion complex. The fluorescence response of this complex is based on the PET mechanism. The inherent fluorescence of C4-CPB is quenched by the internal PET from pyrene to the trigonal form of phenylboronic acid, but saccharide binding converts the boronic acid to the tetrahedral boronate, thereby inhibiting PET quenching and increasing the fluorescence intensity. In a previous study, the spacer effect of the boronic acid probe was examined in detail by using the fluorophores C1-CPB, C4-CPB, and C1-APB (Fig. 1). We found that the C1-APB/β-CD complex was a desirable fluorescent chemosensor for saccharide recognition because of its high affinity to saccharides as well as its relatively high fluorescence recovery upon saccharide binding. Since C1-APB is more soluble than C1-CPB and C4-CPB, because of possessing an amide group, it can be dissolved in water without adding β-CD at the level for the fluorescent measurement. This makes a precise comparison of the CD effect feasible. In the present work, therefore, we focused on C1-APB/CD complexes, and investigated how the sensing function of C1-APB for saccharide recognition in water was affected by differences in An inclusion complex consisting of a fluorescent phenylboronic acid (C1-APB) and β-cyclodextrin (β-CD) acts as a supramolecular saccharide sensor whose response mechanism is based on photoinduced electron transfer (PET). This study evaluated four kinds of cyclodextrins (α-CD, β-CD, γ-CD, and NH2-β-CD) by comparing their pH profiles, and confirmed that β-CD was the best host for C1-APB because the C1-APB/β-CD complex exhibited high affinity for saccharides as well as high fluorescent recovery upon saccharide binding. An ...

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Fluorescent chemosensors of carbohydrates. A means of chemically communicating the binding of polyols in water based on chelation-enhanced quenching

Cited by 471 publications

References 0 publications

Evaluation of Interactions between Monosaccharides and a Stationary Phase Modified with Alkylboronic Acid by Means of a Liquid-Chromatographic Method

Evaluation of Interactions between Monosaccharides and a Stationary Phase Modified with Alkylboronic Acid by Means of a Liquid-Chromatographic Method

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

Effect of Cyclodextrins on Saccharide Sensing Function of a Fluorescent Phenylboronic Acid in Water

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