Isoindoline-based fluorogenic probes bearing a self-immolative linker for the sensitive and selective detection of O-GlcNAcase activity

Yuan-Hao Wu; Guan-Jun Wang; Chen Guo; Pei-Pei Wang; Jun-Yi Wang; Xi-Le Hu; Yi Zang; Tony D. James; Jia Li; Xiao-Peng He

doi:10.1039/D4CC02845G

Isoindoline-based fluorogenic probes bearing a self-immolative linker for the sensitive and selective detection of O-GlcNAcase activity†

Yuan-Hao Wu,‡^a Guan-Jun Wang,‡^a Chen Guo,‡^a Pei-Pei Wang,

^ce Jun-Yi Wang,^l Xi-Le Hu,

*^a Yi Zang,

*^dfg Tony D. James,

*^jk Jia Li

*^cefghi and Xiao-Peng He

*^ab

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* 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, xlhu@ecust.edu.cn

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

^c 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

^d Lingang Laboratory, Shanghai 201203, China
E-mail: yzang@lglab.ac.cn

^e School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing 210023, China

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

^g State Key Laboratory of Chemical Biology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China

^h University of Chinese Academy of Sciences, Beijing, China

ⁱ Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Guangdong 528400, China

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

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

^l Shanghai Starriver Bilingual School, No. 2588 Jindu Road, Minhang District, Shanghai, China

Abstract

O-GlcNAcase (OGA) is implicated in several important biological and disease-relevant processes. Here, we synthesized fluorogenic probes for OGA by grafting GlcNAc directly or using a self-immolative linker to the hydroxyl position of 4-hydroxylisoindoline (BHID), a typical excited-state intramolecular proton transfer (ESIPT) probe. The probe was used for a fluorogenic assay to determine the half maximal inhibitory concentration of a known OGA inhibitor and differentiate between OGA and hexosaminidase when GlcNAc is replaced by GlcNPr, where a propionyl group is used instead of an acetyl group.

This article is part of the themed collection: ChemComm 60th Anniversary Collection

Chemical Communications

Isoindoline-based fluorogenic probes bearing a self-immolative linker for the sensitive and selective detection of O-GlcNAcase activity†

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Isoindoline-based fluorogenic probes bearing a self-immolative linker for the sensitive and selective detection of O-GlcNAcase activity

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