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, Guan Jun Wang, Chen Guo, Pei Pei Wang, Jun Yi Wang, Xi Le Hu, Yi Zang, Tony D. James, Jia Li, Xiao Peng He

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

1 Citation (SciVal)

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.

Original language	English
Pages (from-to)	8240-8243
Number of pages	4
Journal	Chemical Communications
Volume	60
Issue number	63
Early online date	15 Jul 2024
DOIs	https://doi.org/10.1039/d4cc02845g
Publication status	Published - 14 Aug 2024

Data Availability Statement

All data supporting this research are included in the main article and/or ESI.

Acknowledgements

The Research Center of Analysis and Test of East China University of Science and Technology was gratefully acknowledged for assistance in analytical experiments.

Funding

The authors thank the Natural National Science Foundation of China (NSFC) (No. 92253306, 82130099 and 22108077), the Shanghai Municipal Science and Technology Major Project (No. 2018SHZDZX03), the International Cooperation Program of Shanghai Science and Technology (No. 23490711600), the Fundamental Research Funds for the Central Universities (222201717003), the Programme of Introducing Talents of Discipline to Universities (B16017), the Open Funding Project of the State Key Laboratory of Bioreactor Engineering, State Key Laboratory of Drug Research (SKLDR-2023-KF-10) and Ministry of Education Key Laboratory on Signalling Regulation and Targeting Therapy of Liver Cancer (Naval Medical University) (Grant. 2023-MEKLLC-MS/ZD-00*) for financial support. TDJ wishes to thank the University of Bath and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University (2020ZD01) for support.

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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

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.",

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AU - Wu, Yuan Hao

AU - Wang, Guan Jun

AU - Guo, Chen

AU - Wang, Pei Pei

AU - Wang, Jun Yi

AU - Hu, Xi Le

AU - Zang, Yi

AU - James, Tony D.

AU - Li, Jia

AU - He, Xiao Peng

PY - 2024/8/14

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AB - 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.

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

Abstract

Data Availability Statement

Acknowledgements

Funding

ASJC Scopus subject areas

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