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

We synthesized novel PET (photoinduced electron transfer)-type fluorescence glucose probe [(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 a...

Full description

Saved in:
Bibliographic Details
Published in:Frontiers in chemistry 2019-11, Vol.7, p.806-806
Main Authors: Sugita, Ko, Tsuchido, Yuji, Kasahara, Chisato, Casulli, Maria Antonietta, Fujiwara, Shoji, Hashimoto, Takeshi, Hayashita, Takashi
Format: Article
Language:English
Subjects:
boronic acid
Chemistry
cyclodextrin
fluorescence
sugar recognition
supramolecular chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We synthesized novel PET (photoinduced electron transfer)-type fluorescence glucose probe [(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 p 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 with glucose inside a γ-cyclodextrin (γ-CyD) cavity. Selective ratiometric sensing of glucose by the /γ-CyD complex was achieved in water at physiological pH.
ISSN:2296-2646
2296-2646
DOI:10.3389/fchem.2019.00806