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

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Abstract

A boronic acid fluorophore (C1-APB)/boronic acid-modified γ-cyclodextrin (3-PB-γ-CyD) complex as a supramolecular sensor has been designed for selective glucose recognition in water. The fluorescent response behavior of the C1-APB/3-PB-γ-CyD complex under various pH conditions revealed that a C1-APB/3-PB-γ-CyD complex solution containing glucose showed a large increase in the fluorescence intensity under alkaline pH conditions. In contrast, only small increases in the fluorescence intensity were noted for fructose and without sugar solutions. The observed response selectivity for the C1-APB/3-PB-γ-CyD complex was on the order of glucose ≫ galactose, mannose > fructose. The evidence on a large value of the inclusion constant (KL-CyD = 6.5 x 103 M−1), a marked broadening of the 1H NMR spectra, and an enhancement of induced circular dichloism (ICD) intensity for the C1-APB/3-PB-γ-CyD complex by glucose binding supported the multi-point interaction of the C1-APB/3-PB-γ-CyD complex with glucose. These results demonstrated that the C1-APB/3-PB-γ-CyD complex functioned as an efficient supramolecular sensor for selective glucose recognition in water.

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Authors and Affiliations

  1. Department of Life and Material Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, 102-8554, Chiyoda, Tokyo, Japan

    Mio Kumai, Satoko Kozuka, Mariko Samizo, Takeshi Hashimoto & Takashi Hayashita

  2. Department of Pharmacy, Faculty of Pharmacy, Takasaki University of Health and Welfare, 30-1 Nakaorui, 370-0033, Takasaki, Gunma, Japan

    Iwao Suzuki

Authors
  1. Mio Kumai
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  2. Satoko Kozuka
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  3. Mariko Samizo
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  4. Takeshi Hashimoto
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  5. Iwao Suzuki
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  6. Takashi Hayashita
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Correspondence to Takashi Hayashita.

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Kumai, M., Kozuka, S., Samizo, M. et al. Glucose Recognition by a Supramolecular Complex of Boronic Acid Fluorophore with Boronic Acid-Modified Cyclodextrin in Water. ANAL. SCI. 28, 121–126 (2012). https://doi.org/10.2116/analsci.28.121

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  • DOI: https://doi.org/10.2116/analsci.28.121

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