A simple supramolecular complex of boronic acid-appended β-cyclodextrin and a fluorescent boronic acid-based probe with excellent selectivity for d-glucose in water

Ko Sugita; Yota Suzuki; Yuji Tsuchido; Shoji Fujiwara; Takeshi Hashimoto; Takashi Hayashita

doi:10.1039/d2ra03567g

A simple supramolecular complex of boronic acid-appended β-cyclodextrin and a fluorescent boronic acid-based probe with excellent selectivity for d-glucose in water

Ko Sugita, Yota Suzuki, Yuji Tsuchido, Shoji Fujiwara, Takeshi Hashimoto^*, Takashi Hayashita

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

Various diboronic acid-based chemosensors for d-glucose have been developed for use in diabetes diagnostic systems. However, most of these chemosensors have limitations, such as poor water solubility, difficulties in synthesis, and inability to selectively detect d-glucose from among other saccharides. We report a simple chemosensor based on a supramolecular complex of fluorophenylboronic acid-appended β-cyclodextrin (FPB-βCyD) and an anthracene-based probe having a boronic acid moiety (1). Hydrophobic 1 is encapsulated in the cyclodextrin cavity of FPB-βCyD, making the supramolecular complex (1/FPB-βCyD) applicable in a water-rich solvent mixture (98% water). Interestingly, 1/FPB-βCyD showed a strong turn-on response to d-glucose with a 9.6-fold enhancement in fluorescence intensity, and no response to other saccharides. This study uncovers an innovative approach based on the supramolecular assembly of simple components for the development of a water-soluble d-glucose chemosensor with excellent selectivity.

Original language	English
Pages (from-to)	20259-20263
Number of pages	5
Journal	RSC Advances
Volume	12
Issue number	31
DOIs	https://doi.org/10.1039/d2ra03567g
Publication status	Published - 2022 Jul 14

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

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title = "A simple supramolecular complex of boronic acid-appended β-cyclodextrin and a fluorescent boronic acid-based probe with excellent selectivity for d-glucose in water",

abstract = "Various diboronic acid-based chemosensors for d-glucose have been developed for use in diabetes diagnostic systems. However, most of these chemosensors have limitations, such as poor water solubility, difficulties in synthesis, and inability to selectively detect d-glucose from among other saccharides. We report a simple chemosensor based on a supramolecular complex of fluorophenylboronic acid-appended β-cyclodextrin (FPB-βCyD) and an anthracene-based probe having a boronic acid moiety (1). Hydrophobic 1 is encapsulated in the cyclodextrin cavity of FPB-βCyD, making the supramolecular complex (1/FPB-βCyD) applicable in a water-rich solvent mixture (98% water). Interestingly, 1/FPB-βCyD showed a strong turn-on response to d-glucose with a 9.6-fold enhancement in fluorescence intensity, and no response to other saccharides. This study uncovers an innovative approach based on the supramolecular assembly of simple components for the development of a water-soluble d-glucose chemosensor with excellent selectivity.",

author = "Ko Sugita and Yota Suzuki and Yuji Tsuchido and Shoji Fujiwara and Takeshi Hashimoto and Takashi Hayashita",

note = "Funding Information: This research was financially supported by Japan Society for the Promotion of Science (JSPS) Grants-in-Aid for Scientific Research Grant Numbers 20H02772 (T. Hay.), 18K05180 (T. Has.), 21K03452 (T. Has.), and 18K14255 (Y. T.), and a JSPS Research Fellowship for Young Scientists PD Grant Number 21J00709 (Y. S.). Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",

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AU - Sugita, Ko

AU - Suzuki, Yota

AU - Tsuchido, Yuji

AU - Fujiwara, Shoji

AU - Hashimoto, Takeshi

AU - Hayashita, Takashi

N1 - Funding Information: This research was financially supported by Japan Society for the Promotion of Science (JSPS) Grants-in-Aid for Scientific Research Grant Numbers 20H02772 (T. Hay.), 18K05180 (T. Has.), 21K03452 (T. Has.), and 18K14255 (Y. T.), and a JSPS Research Fellowship for Young Scientists PD Grant Number 21J00709 (Y. S.). Publisher Copyright: © 2022 The Royal Society of Chemistry.

PY - 2022/7/14

Y1 - 2022/7/14

N2 - Various diboronic acid-based chemosensors for d-glucose have been developed for use in diabetes diagnostic systems. However, most of these chemosensors have limitations, such as poor water solubility, difficulties in synthesis, and inability to selectively detect d-glucose from among other saccharides. We report a simple chemosensor based on a supramolecular complex of fluorophenylboronic acid-appended β-cyclodextrin (FPB-βCyD) and an anthracene-based probe having a boronic acid moiety (1). Hydrophobic 1 is encapsulated in the cyclodextrin cavity of FPB-βCyD, making the supramolecular complex (1/FPB-βCyD) applicable in a water-rich solvent mixture (98% water). Interestingly, 1/FPB-βCyD showed a strong turn-on response to d-glucose with a 9.6-fold enhancement in fluorescence intensity, and no response to other saccharides. This study uncovers an innovative approach based on the supramolecular assembly of simple components for the development of a water-soluble d-glucose chemosensor with excellent selectivity.

AB - Various diboronic acid-based chemosensors for d-glucose have been developed for use in diabetes diagnostic systems. However, most of these chemosensors have limitations, such as poor water solubility, difficulties in synthesis, and inability to selectively detect d-glucose from among other saccharides. We report a simple chemosensor based on a supramolecular complex of fluorophenylboronic acid-appended β-cyclodextrin (FPB-βCyD) and an anthracene-based probe having a boronic acid moiety (1). Hydrophobic 1 is encapsulated in the cyclodextrin cavity of FPB-βCyD, making the supramolecular complex (1/FPB-βCyD) applicable in a water-rich solvent mixture (98% water). Interestingly, 1/FPB-βCyD showed a strong turn-on response to d-glucose with a 9.6-fold enhancement in fluorescence intensity, and no response to other saccharides. This study uncovers an innovative approach based on the supramolecular assembly of simple components for the development of a water-soluble d-glucose chemosensor with excellent selectivity.

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A simple supramolecular complex of boronic acid-appended β-cyclodextrin and a fluorescent boronic acid-based probe with excellent selectivity for d-glucose in water

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