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Sugar-dependent solubility and fluorescence property of copolymers consisting of phenylboronic acid and 2-hydroxyethyl methacrylate moieties

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Abstract

Copolymers consisting of N-3-acrylamidophenylboronic acid (APBA) and 2-hydroxyethyl methacrylate moieties (HEMA) were synthesized and their solubility and fluorescence properties were evaluated in the presence of sugar. The APBA–HEMA copolymer composed of 25 mol% of APBA moiety was found to be poorly soluble in water at pH 7.4. However, the water solubility of APBA–HEMA was improved in the presence of fructose in solution. The solubility of APBA–HEMA was influenced by fructose in a concentration-dependent manner, due to the formation of boronate ester of APBA moiety with fructose added. In addition, APBA–HEMA was modified with fluorescein isothiocyanate (FITC) for the fluorometric detection of sugars. The fluorescence intensity of FITC-modified APBA–HEMA was dependent on the type and concentration of sugars in solution. The fluorescence intensity of FITC-modified APBA–HEMA was highly enhanced by the addition of fructose, while the fluorescent response was negligibly small when other sugars were added. Thus, usefulness of FITC-modified APBA–HEMA for the selective determination of fructose was demonstrated.

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Acknowledgment

This study was supported, in part, by a Grant-in-Aid for Young Scientists (B) (21790031) from Japan Society for Promotion of Sciences (JSPS).

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Authors and Affiliations

  1. Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, Sendai, 980-8578, Japan

    Katsuhiko Sato, Tatsuya Nakajima, Yu Yasukawa & Jun-ichi Anzai

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  1. Katsuhiko Sato
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  2. Tatsuya Nakajima
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  3. Yu Yasukawa
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  4. Jun-ichi Anzai
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Correspondence to Jun-ichi Anzai.

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Sato, K., Nakajima, T., Yasukawa, Y. et al. Sugar-dependent solubility and fluorescence property of copolymers consisting of phenylboronic acid and 2-hydroxyethyl methacrylate moieties. Polym. Bull. 65, 807–814 (2010). https://doi.org/10.1007/s00289-010-0278-x

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