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Original Research ARTICLE Provisionally accepted The full-text will be published soon. Notify me

Front. Chem. | doi: 10.3389/fchem.2019.00806

Selective Sugar Recognition by Anthracene-Type Boronic Acid Fluorophore/Cyclodextrin Supramolecular Complex under Physiological pH Condition

 Ko Sugita1,  Yuji Tsuchido1, 2, Chisato Kasahara1, Maria A. Casulli1, Shoji Fujiwara1, 3, Takeshi Hashimoto1 and  Takashi Hayashita1*
  • 1Department of Materials and Life Sciences, Sophia University, Japan
  • 2Department of Life Science and Medical Bioscience, Waseda University, Japan
  • 3Department of Current Legal Studies, Meiji Gakuin University, Japan

We synthesized novel PET (photoinduced electron transfer) type fluorescence glucose probe 1 ((4-(anthracen-2-yl-carbamoyl)-3-fluorophenyl)boronic acid), which has a phenylboronic acid (PBA) moiety as the recognition site and anthracene as the fluorescent part. Although the PBA derivatives dissociate and bind with sugar in the basic condition, our new fluorescent probe can recognize sugars in the physiological pH by introducing an electron-withdrawing fluorine group into the PBA moiety. As a result, the pKa value of this fluorescent probe was lowered and the probe was able to recognize sugars at the physiological pH of 7.4. The sensor was found to produce two types of fluorescent signals, monomer fluorescence and dimer fluorescence, by forming a supramolecular 2:1 complex of 1 with glucose inside a gamma-cyclodextrin (gamma-CyD) cavity. Selective ratiometric sensing of glucose by the 1/gamma-CyD complex was achieved in water at physiological pH.

Keywords: Cyclodextrin, Boronic acid, supramolecular chemistry, fluorescence, Sugar recognition

Received: 30 Sep 2019; Accepted: 08 Nov 2019.

Copyright: © 2019 Sugita, Tsuchido, Kasahara, Casulli, Fujiwara, Hashimoto and Hayashita. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

* Correspondence: Prof. Takashi Hayashita, Sophia University, Department of Materials and Life Sciences, Chiyoda, Tokyo, 102-8554, Tōkyō, Japan, ta-hayas@sophia.ac.jp