Ratiometric sensing of β-galactosidase based on excited-state intramolecular proton transfer (ESIPT) and solid-state luminescence enhancement

He Tian; Wei Lin; Xi-Le Hu; Jing-Bo Wang; Min-Yu Zhang; Yi Zang; Xin-Yan Wu; Jia Li; Tony D. James; Xiao-Peng He

doi:10.1039/D3QO00605K

Ratiometric sensing of β-galactosidase based on excited-state intramolecular proton transfer (ESIPT) and solid-state luminescence enhancement†

He Tian, Jr.,

^a Wei Lin,

^a Xi-Le Hu,

^a Jing-Bo Wang,

^a Min-Yu Zhang,

^a Yi Zang,

^bfg Xin-Yan Wu,

^a Jia Li,

*^bf Tony D. James

*^de and Xiao-Peng He

*^ac

Author affiliations

* Corresponding authors

^a Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Rd, Shanghai 200237, China
E-mail: xphe@ecust.edu.cn

^b National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
E-mail: jli@simm.ac.cn

^c National Center for Liver Cancer, The International Cooperation Laboratory on Signal Transduction, Eastern Hepatobiliary Surgery Hospital, Shanghai 200438, China

^d Department of Chemistry, University of Bath, Bath, UK
E-mail: t.d.james@bath.ac.uk

^e School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

^f School of Pharmaceutical Science and Technology, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, China

^g Lingang Laboratory, Shanghai 201203, China

Abstract

Glycosidases play important roles in modulating the structural and functional integrity of glycoproteins and glycolipids, and thus are promising biomarkers for disease diagnosis. While current approaches for glycosidase detection mainly rely on an enhancement of the UV-vis absorbance or fluorescence emission of glycosyl indicators, here we develop a ratiometric fluorescent probe for the sensitive and selective detection of glycosidase activity based on the combined mechanisms of excited-state intramolecular proton transfer (ESIPT) and solid-state luminescence enhancement (SSLE). The probe behaves like a typical SSLE when glycosylated, and exhibits a ∼140 nm red-shift in fluorescence owing to activation of ESIPT after deglycosylation. Such a large Stokes shift may facilitate the unbiased analysis of glycosidase activities when used in diagnostic and drug-screening assays.

This article is part of the themed collection: In memory of John S. Fossey – CAtalysis and SEnsing (CASE)

Organic Chemistry Frontiers

Ratiometric sensing of β-galactosidase based on excited-state intramolecular proton transfer (ESIPT) and solid-state luminescence enhancement†

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Ratiometric sensing of β-galactosidase based on excited-state intramolecular proton transfer (ESIPT) and solid-state luminescence enhancement

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