A BODIPY-tagged trivalent glycocluster for receptor-targeting fluorescence imaging of live cells

Chen Guo; Fang-Yu Si; Chen-Han Wang; Ning Wang; Xi Le Hu; Tony James; Jia Li; Chengyun Wang; Xiao-Peng He

doi:10.1039/D4SC08472A

A BODIPY-tagged trivalent glycocluster for receptor-targeting fluorescence imaging of live cells

Chen Guo, Fang-Yu Si, Chen-Han Wang, Ning Wang, Xi Le Hu, Tony James, Jia Li, Chengyun Wang, Xiao-Peng He

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

Abstract

Multivalent glycoclusters have been extensively used as a targeting agent for drug delivery. However, tools capable of investigating their dynamic interactions with a target receptor remain elusive. Here, we synthesized fluorescently-tagged galactoclusters for the fluorescence imaging of cells that overly express the asialoglycoprotein receptor (ASGPr). A trivalent galactoside was synthesized, to which a boron dipyrromethene (BODIPY) dye was conjugated. The resulting fluorescent glycocluster was used for the targeted fluorescence imaging of liver cancer cells with a high ASGPr expression level. The trivalent probe was also demonstrated to be applicable for super-resolution imaging of ASGPr-mediated ligand endocytosis and the dynamic intracellular translocation to the lysosomes. As such, this study provides a suitable chemical tool for the study of receptor dynamics using fluorescently tagged glycoclusters.

Original language	English
Journal	Chemical Science
Early online date	27 May 2025
DOIs	https://doi.org/10.1039/D4SC08472A
Publication status	E-pub ahead of print - 27 May 2025

Data Availability Statement

All data generated during this study have been included as part of the ESI.†1H and 13C-NMR spectra for unreported compounds can be found in the 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 22477030), Science and Technology Commission of Shanghai Municipality (grant No. 24DX1400200), 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 National Natural Science Foundation of Shanghai Science and Technology (No. 24ZR1415400), the Shanghai Oriental Talents youth Program (No. QNKJ2024010), the Shanghai Xuhui District Hospital Local Cooperation Project (23XHYD-20), the Open Funding Project of the State Key Laboratory of Fine Chemicals, Dalian University of Technology (KF 2402), State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, P. R. China, Ministry of Education Key Laboratory on signaling Regulation and Targeting Therapy of Liver Cancer (Naval Medical University) (Grant. 2023-MEKLLC-MS/ZD-00*) and Shandong Laboratory Program (SYS202205) for financial support. T. D. J. 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. The Research Center of Analysis and Test of East China University of Science and Technology was gratefully acknowledged for assistance in analytical experiments.

Funders	Funder number
State Key Laboratory of Catalysis
Ministry of Education Key Laboratory on signaling Regulation and Targeting Therapy of Liver Cancer
University of Bath
State Key Laboratory of Fine Chemicals
Shandong Laboratory Program	SYS202205
Henan Normal University	2020ZD01
Dalian University of Technology	KF 2402
Shanghai Xuhui District Hospital	23XHYD-20
Fundamental Research Funds for the Central Universities	222201717003
Project 211	B16017
Science and Technology Commission of Shanghai Municipality	24DX1400200
Biosensing and Chemometrics, Hunan University	410082
Shanghai Science and Technology Development Foundation	24ZR1415400
National Natural Science Foundation of China	82130099, 22477030, 92253306
Shanghai Oriental Talents youth Program	QNKJ2024010
International Science and Technology Cooperation Programme	23490711600
Naval Medical University	2023-MEKLLC-MS/ZD-00*

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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Cite this

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title = "A BODIPY-tagged trivalent glycocluster for receptor-targeting fluorescence imaging of live cells",

abstract = "Multivalent glycoclusters have been extensively used as a targeting agent for drug delivery. However, tools capable of investigating their dynamic interactions with a target receptor remain elusive. Here, we synthesized fluorescently-tagged galactoclusters for the fluorescence imaging of cells that overly express the asialoglycoprotein receptor (ASGPr). A trivalent galactoside was synthesized, to which a boron dipyrromethene (BODIPY) dye was conjugated. The resulting fluorescent glycocluster was used for the targeted fluorescence imaging of liver cancer cells with a high ASGPr expression level. The trivalent probe was also demonstrated to be applicable for super-resolution imaging of ASGPr-mediated ligand endocytosis and the dynamic intracellular translocation to the lysosomes. As such, this study provides a suitable chemical tool for the study of receptor dynamics using fluorescently tagged glycoclusters.",

author = "Chen Guo and Fang-Yu Si and Chen-Han Wang and Ning Wang and Hu, {Xi Le} and Tony James and Jia Li and Chengyun Wang and Xiao-Peng He",

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AU - Guo, Chen

AU - Si, Fang-Yu

AU - Wang, Chen-Han

AU - Wang, Ning

AU - Hu, Xi Le

AU - James, Tony

AU - Li, Jia

AU - Wang, Chengyun

AU - He, Xiao-Peng

PY - 2025/5/27

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N2 - Multivalent glycoclusters have been extensively used as a targeting agent for drug delivery. However, tools capable of investigating their dynamic interactions with a target receptor remain elusive. Here, we synthesized fluorescently-tagged galactoclusters for the fluorescence imaging of cells that overly express the asialoglycoprotein receptor (ASGPr). A trivalent galactoside was synthesized, to which a boron dipyrromethene (BODIPY) dye was conjugated. The resulting fluorescent glycocluster was used for the targeted fluorescence imaging of liver cancer cells with a high ASGPr expression level. The trivalent probe was also demonstrated to be applicable for super-resolution imaging of ASGPr-mediated ligand endocytosis and the dynamic intracellular translocation to the lysosomes. As such, this study provides a suitable chemical tool for the study of receptor dynamics using fluorescently tagged glycoclusters.

AB - Multivalent glycoclusters have been extensively used as a targeting agent for drug delivery. However, tools capable of investigating their dynamic interactions with a target receptor remain elusive. Here, we synthesized fluorescently-tagged galactoclusters for the fluorescence imaging of cells that overly express the asialoglycoprotein receptor (ASGPr). A trivalent galactoside was synthesized, to which a boron dipyrromethene (BODIPY) dye was conjugated. The resulting fluorescent glycocluster was used for the targeted fluorescence imaging of liver cancer cells with a high ASGPr expression level. The trivalent probe was also demonstrated to be applicable for super-resolution imaging of ASGPr-mediated ligand endocytosis and the dynamic intracellular translocation to the lysosomes. As such, this study provides a suitable chemical tool for the study of receptor dynamics using fluorescently tagged glycoclusters.

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A BODIPY-tagged trivalent glycocluster for receptor-targeting fluorescence imaging of live cells

Abstract

Data Availability Statement

Acknowledgements

Funding

UN SDGs

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