TY - JOUR
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.
UR - http://www.scopus.com/inward/record.url?scp=85152147778&partnerID=8YFLogxK
U2 - 10.1021/jacs.2c13694
DO - 10.1021/jacs.2c13694
M3 - Article
C2 - 37023253
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 -
