Reversible Recognition-Based Boronic Acid Probes for Glucose Detection in Live Cells and Zebrafish

Kai Wang; Ruixiao Zhang; Xiujie Zhao; Yan Ma; Lijuan Ren; Youxiao Ren; Gaofei Chen; Dingming Ye; Jinfang Wu; Xinyuan Hu; Yuanqiang Guo; Rimo Xi; Meng Meng; Qingqiang Yao; Ping Li; Qixin Chen; Tony D. James

doi:10.1021/jacs.2c13694

Reversible Recognition-Based Boronic Acid Probes for Glucose Detection in Live Cells and Zebrafish

Kai Wang, Ruixiao Zhang, Xiujie Zhao, Yan Ma, Lijuan Ren, Youxiao Ren, Gaofei Chen, Dingming Ye, Jinfang Wu, Xinyuan Hu, Yuanqiang Guo, Rimo Xi, Meng Meng, Qingqiang Yao, Ping Li, Qixin Chen, Tony D. James

Department of Chemistry

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

32 Citations (SciVal)

Abstract

Glucose, a critical source of energy, directly determines the homeostasis of the human body. However, due to the lack of robust imaging probes, the mechanism underlying the changes of glucose homeostasis in the human body remains unclear. Herein, diboronic acid probes with good biocompatibility and high sensitivity were synthesized based on an ortho-aminomethylphenylboronic acid probe, phenyl(di)boronic acid (PDBA). Significantly, by introducing the water-solubilizing group −CN directly opposite the boronic acid group and −COOCH₃ or −COOH groups to the β site of the anthracene in PDBA, we obtained the water-soluble probe Mc-CDBA with sensitive response (F/F₀ = 47.8, detection limit (LOD) = 1.37 μM) and Ca-CDBA with the highest affinity for glucose (K_a = 4.5 × 10³ M^-1). On this basis, Mc-CDBA was used to identify glucose heterogeneity between normal and tumor cells. Finally, Mc-CDBA and Ca-CDBA were used for imaging glucose in zebrafish. Our research provides a new strategy for designing efficient boronic acid glucose probes and powerful new tools for the evaluation of glucose-related diseases.

Original language	English
Pages (from-to)	8408-8416
Journal	Journal of the American Chemical Society
Volume	145
Issue number	15
Early online date	6 Apr 2023
DOIs	https://doi.org/10.1021/jacs.2c13694
Publication status	Published - 16 Apr 2023

Bibliographical note

Funding Information:
This work was supported by the Natural Science Foundation of Tianjin, China (No. 21JCZDJC00200), Academic Promotion Program of Shandong First Medical University (2019LJ003), National Natural Science Foundation of China (Nos. 22107059 and 22007060), Shandong Province Key R&D Program (Major Technological Innovation Project) (2021CXGC010501), Natural Science Foundation of Shandong Province (ZR2021QH057, ZR2022QH304, and ZR2020QB166), Innovation Team of Shandong Higher School Youth Innovation Technology Program (2021KJ035), Taishan Scholars Young Experts Program (TSQN202211221), Shandong Excellent Youth Fund (ZR2022YQ66). T.D.J. wishes to thank the Royal Society for a Wolfson Research Merit Award and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University for support (2020ZD01).

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

UN SDGs

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

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10.1021/jacs.2c13694Licence: CC BY

Cite this

@article{228cd356fec04d419507986fd35e42b2,

title = "Reversible Recognition-Based Boronic Acid Probes for Glucose Detection in Live Cells and Zebrafish",

abstract = "Glucose, a critical source of energy, directly determines the homeostasis of the human body. However, due to the lack of robust imaging probes, the mechanism underlying the changes of glucose homeostasis in the human body remains unclear. Herein, diboronic acid probes with good biocompatibility and high sensitivity were synthesized based on an ortho-aminomethylphenylboronic acid probe, phenyl(di)boronic acid (PDBA). Significantly, by introducing the water-solubilizing group −CN directly opposite the boronic acid group and −COOCH3 or −COOH groups to the β site of the anthracene in PDBA, we obtained the water-soluble probe Mc-CDBA with sensitive response (F/F0 = 47.8, detection limit (LOD) = 1.37 μM) and Ca-CDBA with the highest affinity for glucose (Ka = 4.5 × 103 M-1). On this basis, Mc-CDBA was used to identify glucose heterogeneity between normal and tumor cells. Finally, Mc-CDBA and Ca-CDBA were used for imaging glucose in zebrafish. Our research provides a new strategy for designing efficient boronic acid glucose probes and powerful new tools for the evaluation of glucose-related diseases.",

author = "Kai Wang and Ruixiao Zhang and Xiujie Zhao and Yan Ma and Lijuan Ren and Youxiao Ren and Gaofei Chen and Dingming Ye and Jinfang Wu and Xinyuan Hu and Yuanqiang Guo and Rimo Xi and Meng Meng and Qingqiang Yao and Ping Li and Qixin Chen and James, {Tony D.}",

note = "Funding Information: This work was supported by the Natural Science Foundation of Tianjin, China (No. 21JCZDJC00200), Academic Promotion Program of Shandong First Medical University (2019LJ003), National Natural Science Foundation of China (Nos. 22107059 and 22007060), Shandong Province Key R&D Program (Major Technological Innovation Project) (2021CXGC010501), Natural Science Foundation of Shandong Province (ZR2021QH057, ZR2022QH304, and ZR2020QB166), Innovation Team of Shandong Higher School Youth Innovation Technology Program (2021KJ035), Taishan Scholars Young Experts Program (TSQN202211221), Shandong Excellent Youth Fund (ZR2022YQ66). T.D.J. wishes to thank the Royal Society for a Wolfson Research Merit Award and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University for support (2020ZD01). ",

year = "2023",

month = apr,

day = "16",

doi = "10.1021/jacs.2c13694",

language = "English",

volume = "145",

pages = "8408--8416",

journal = "Journal of the American Chemical Society",

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T1 - Reversible Recognition-Based Boronic Acid Probes for Glucose Detection in Live Cells and Zebrafish

AU - Wang, Kai

AU - Zhang, Ruixiao

AU - Zhao, Xiujie

AU - Ma, Yan

AU - Ren, Lijuan

AU - Ren, Youxiao

AU - Chen, Gaofei

AU - Ye, Dingming

AU - Wu, Jinfang

AU - Hu, Xinyuan

AU - Guo, Yuanqiang

AU - Xi, Rimo

AU - Meng, Meng

AU - Yao, Qingqiang

AU - Li, Ping

AU - Chen, Qixin

AU - James, Tony D.

N1 - Funding Information: This work was supported by the Natural Science Foundation of Tianjin, China (No. 21JCZDJC00200), Academic Promotion Program of Shandong First Medical University (2019LJ003), National Natural Science Foundation of China (Nos. 22107059 and 22007060), Shandong Province Key R&D Program (Major Technological Innovation Project) (2021CXGC010501), Natural Science Foundation of Shandong Province (ZR2021QH057, ZR2022QH304, and ZR2020QB166), Innovation Team of Shandong Higher School Youth Innovation Technology Program (2021KJ035), Taishan Scholars Young Experts Program (TSQN202211221), Shandong Excellent Youth Fund (ZR2022YQ66). T.D.J. wishes to thank the Royal Society for a Wolfson Research Merit Award and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University for support (2020ZD01).

PY - 2023/4/16

Y1 - 2023/4/16

N2 - Glucose, a critical source of energy, directly determines the homeostasis of the human body. However, due to the lack of robust imaging probes, the mechanism underlying the changes of glucose homeostasis in the human body remains unclear. Herein, diboronic acid probes with good biocompatibility and high sensitivity were synthesized based on an ortho-aminomethylphenylboronic acid probe, phenyl(di)boronic acid (PDBA). Significantly, by introducing the water-solubilizing group −CN directly opposite the boronic acid group and −COOCH3 or −COOH groups to the β site of the anthracene in PDBA, we obtained the water-soluble probe Mc-CDBA with sensitive response (F/F0 = 47.8, detection limit (LOD) = 1.37 μM) and Ca-CDBA with the highest affinity for glucose (Ka = 4.5 × 103 M-1). On this basis, Mc-CDBA was used to identify glucose heterogeneity between normal and tumor cells. Finally, Mc-CDBA and Ca-CDBA were used for imaging glucose in zebrafish. Our research provides a new strategy for designing efficient boronic acid glucose probes and powerful new tools for the evaluation of glucose-related diseases.

AB - Glucose, a critical source of energy, directly determines the homeostasis of the human body. However, due to the lack of robust imaging probes, the mechanism underlying the changes of glucose homeostasis in the human body remains unclear. Herein, diboronic acid probes with good biocompatibility and high sensitivity were synthesized based on an ortho-aminomethylphenylboronic acid probe, phenyl(di)boronic acid (PDBA). Significantly, by introducing the water-solubilizing group −CN directly opposite the boronic acid group and −COOCH3 or −COOH groups to the β site of the anthracene in PDBA, we obtained the water-soluble probe Mc-CDBA with sensitive response (F/F0 = 47.8, detection limit (LOD) = 1.37 μM) and Ca-CDBA with the highest affinity for glucose (Ka = 4.5 × 103 M-1). On this basis, Mc-CDBA was used to identify glucose heterogeneity between normal and tumor cells. Finally, Mc-CDBA and Ca-CDBA were used for imaging glucose in zebrafish. Our research provides a new strategy for designing efficient boronic acid glucose probes and powerful new tools for the evaluation of glucose-related diseases.

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DO - 10.1021/jacs.2c13694

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AN - SCOPUS:85152147778

SN - 0002-7863

VL - 145

SP - 8408

EP - 8416

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 15

ER -

Reversible Recognition-Based Boronic Acid Probes for Glucose Detection in Live Cells and Zebrafish

Abstract

Bibliographical note

ASJC Scopus subject areas

UN SDGs

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