Glucose Recognition by a Supramolecular Complex of Boronic Acid Fluorophore with Boronic Acid-Modified Cyclodextrin in Water

Kumai, Mio; Kozuka, Satoko; Samizo, Mariko; Hashimoto, Takeshi; Suzuki, I.; Hayashita, Takashi

doi:10.2116/analsci.28.121

Cited by 43 publications

(34 citation statements)

References 18 publications

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“…However, upon addition of metal ions, the receptor chelates the metal ions to form stable complexes, thereby deactivating the quenching by PET due to stabilization of the receptor's HOMO so that it lies below the energy level of the fluorophore's HOMO, and increasing the fluorescence intensity of the coumarin moiety. 15,16 Such transition metals as Fe 2+ , Ni 2+ , Cr 2+ , Cu 2+ , and Co 2+ are paramagnetic ions with an unfilled d shell, and are known to induce fluorescence quenching. Though Fe 2+ and Ni 2+ can take both high-spin and low-spin states, it is known that the fluorescence was quenched by the paramagnetic metal ions with a high-spin state.…”

Section: Metal Ion Selectivity Of Dpa-hc In An Aqueous Solventmentioning

confidence: 99%

Solvent Effect on the Fluorescence Response of Hydroxycoumarin Bearing a Dipicolylamine Binding Site to Metal Ions

et al. 2014

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The fluorescence behavior of a probe dpa-HC, which has a coumarin derivative that acts as a fluorophore and a dipicolylamine (DPA) unit that functions as a metal ion-recognition site, was investigated with various metal ions in aqueous and several non-aqueous solvents. In aqueous solution, the fluorescence of dpa-HC was enhanced by Zn 2+ and Cd 2+ , but was quenched by other metal ions. On the other hand, in an acetonitrile solution, only Mg 2+ enhanced the fluorescence, and the addition of a small amount of water quenched this fluorescence. This dramatic selectivity change is explained by stabilization of a metal-dpa-HC complex due to acetonitrile coordination and ON-OFF switching of the intramolecular photoinduced electron transfer (PET) from the nitrogen lone pair of DPA to the coumarin derivative. Scheme 1 Synthesis of 8-(2,2′-dipicolylaminomethyl)-7-hydroxycoumarin (dpa-HC). Keywords

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Section: Metal Ion Selectivity Of Dpa-hc In An Aqueous Solventmentioning

confidence: 99%

Solvent Effect on the Fluorescence Response of Hydroxycoumarin Bearing a Dipicolylamine Binding Site to Metal Ions

et al. 2014

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“…1, soyasaponin Bb has one carboxyl group and two cis-diol groups, which react with borate anion to form a negatively charged ester. [14][15][16] In the borax solution, the borate anion would be formed according to the following reaction: B4O7 2-+ 7H2O = 2B(OH)4 -+ 2B(OH)3.…”

Section: Ce Of Standard Materials Of Soyasaponins Bb and Bamentioning

confidence: 99%

Simple and Rapid Separation of Soyasaponin Bb from a Soy Extract

et al. 2015

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Soyasaponins Ba and Bb were obtained from Funakoshi Co., Ltd., and were used as standard materials. A crude soyasaponin was purchased from Fuji Oil Co., Ltd., and used as the starting material. Other chemicals were of reagent grade, and were used 2015 © The Japan Society for Analytical Chemistry † To whom correspondence should be addressed. A simple method to separate soyasaponin Bb from a soy extract is presented. This method is based on the difference in the solubility of soyasaponin Bb and Ba and other components into 3:7 and 1:1 (v/v) acetone-water mixed solvents. The crude soyasaponin consisting of soyasaponins Aa, Ab, Ba, and Bb at the 10 wt% level and other components was examined as the soy extract. A 10 mg quantity of the crude soyasaponin was mixed with 1 mL of the 3:7 acetone-water containing 0.1 mol/L HCl, and the supernatant was removed to obtain a precipitate, which was found to contain mainly soyasaponins Bb and Ba. The precipitate was mixed with 0.4 mL of the 1:1 acetone-water containing 0.1 mol/L HCl; the supernatant was transferred, and was mixed with 0.6 mL of water to obtain a precipitate, which was found to contain mainly soyasaponin Bb. The yield was ca. 30%, which may be much higher than that by the conventional preparative chromatographic approach. The separation method is rapid and easy to carry out, and is useful for the preparation of a soyasaponin Bb sample.

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“…20,21 Water was doubly distilled and deionized by a Milli-Q water system (WG222, Yamato Scientific Co., Ltd., Tokyo, Japan and Autopure WR-600G, Merck Millipore, MA) before use. DMSO was purchased from Dojindo Molecular Technologies, Inc. ).…”

Section: Reagents and Chemicalsmentioning

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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Glucose Recognition by a Supramolecular Complex of Boronic Acid Fluorophore with Boronic Acid-Modified Cyclodextrin in Water

Cited by 43 publications

References 18 publications

Solvent Effect on the Fluorescence Response of Hydroxycoumarin Bearing a Dipicolylamine Binding Site to Metal Ions

Solvent Effect on the Fluorescence Response of Hydroxycoumarin Bearing a Dipicolylamine Binding Site to Metal Ions

Simple and Rapid Separation of Soyasaponin Bb from a Soy Extract

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

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