Synthesis of Bisboronic Acids and Their Selective Recognition of Sialyl Lewis X Antigen

doi:10.1007/s40242-018-7328-6

高等学校化学研究 ›› 2018, Vol. 34 ›› Issue (3): 415-422.doi: 10.1007/s40242-018-7328-6

Synthesis of Bisboronic Acids and Their Selective Recognition of Sialyl Lewis X Antigen

WANG Yan'en^1,2, LI Xueyan¹, CHEN Hua¹, ZHU Mengyuan³, LI Xiaoliu¹

1. Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, P. R. China;
2. College of Science, Agricultural University of Hebei, Baoding 071001, P. R. China;
3. Department of Chemistry and Center for Diagnostics and Therapeutics, Georgia State University, Atlanta, GA 30303, USA

收稿日期:2017-10-17 修回日期:2018-03-30 出版日期:2018-06-01 发布日期:2018-04-16
通讯作者: CHEN Hua, LI Xiaoliu E-mail:lixl@hbu.cn;hua-todd@163.com
基金资助:
Supported by the National Natural Science Foundation of China(No.21372060), the Natural Science Fund for Distinguished Young Scholars of Hebei Province, China(No.B2015201005), the Natural Science Foundation of Hebei Province, China (No.B2018201234) and the Foundation of Hebei Education Department, China (No.QB2017015).

Synthesis of Bisboronic Acids and Their Selective Recognition of Sialyl Lewis X Antigen

WANG Yan'en^1,2, LI Xueyan¹, CHEN Hua¹, ZHU Mengyuan³, LI Xiaoliu¹

1. Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, P. R. China;
2. College of Science, Agricultural University of Hebei, Baoding 071001, P. R. China;
3. Department of Chemistry and Center for Diagnostics and Therapeutics, Georgia State University, Atlanta, GA 30303, USA

Received:2017-10-17 Revised:2018-03-30 Online:2018-06-01 Published:2018-04-16
Contact: CHEN Hua, LI Xiaoliu E-mail:lixl@hbu.cn;hua-todd@163.com
Supported by:
Supported by the National Natural Science Foundation of China(No.21372060), the Natural Science Fund for Distinguished Young Scholars of Hebei Province, China(No.B2015201005), the Natural Science Foundation of Hebei Province, China (No.B2018201234) and the Foundation of Hebei Education Department, China (No.QB2017015).

摘要/Abstract

摘要： The development of sensors that recognize Lewis oligosaccharides can help the diagnosis and early detection of cancer. Herein, we reported the design and synthesis of a series of anthracene-based bisboronic acids (9a-9e) with different N-substituents near the boronic acid unit. Among them, compound 9a could recognize sialyl Lewis X(sLe^x) with selectivity over other Lewis sugars, and could significantly stain sLe^x-expressing HEPG2 cells with selectivity over the range of 0.1-10 μmol/L. Compound 9a possibly has two properly positioned boronic acids caused by the steric hindrance by the near N-benzyl substituent group, which empower its sLe^x selectivity and higher binding affinity.

关键词: Lewis sugar, Bisboronic acid, Anthracene-based fluorescent probe, Biochemical recognition

Abstract: The development of sensors that recognize Lewis oligosaccharides can help the diagnosis and early detection of cancer. Herein, we reported the design and synthesis of a series of anthracene-based bisboronic acids (9a-9e) with different N-substituents near the boronic acid unit. Among them, compound 9a could recognize sialyl Lewis X(sLe^x) with selectivity over other Lewis sugars, and could significantly stain sLe^x-expressing HEPG2 cells with selectivity over the range of 0.1-10 μmol/L. Compound 9a possibly has two properly positioned boronic acids caused by the steric hindrance by the near N-benzyl substituent group, which empower its sLe^x selectivity and higher binding affinity.

Key words: Lewis sugar, Bisboronic acid, Anthracene-based fluorescent probe, Biochemical recognition

WANG Yan'en, LI Xueyan, CHEN Hua, ZHU Mengyuan, LI Xiaoliu. Synthesis of Bisboronic Acids and Their Selective Recognition of Sialyl Lewis X Antigen[J]. 高等学校化学研究, 2018, 34(3): 415-422.

WANG Yan'en, LI Xueyan, CHEN Hua, ZHU Mengyuan, LI Xiaoliu. Synthesis of Bisboronic Acids and Their Selective Recognition of Sialyl Lewis X Antigen[J]. Chemical Research in Chinese Universities, 2018, 34(3): 415-422.

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Synthesis of Bisboronic Acids and Their Selective Recognition of Sialyl Lewis X Antigen

Synthesis of Bisboronic Acids and Their Selective Recognition of Sialyl Lewis X Antigen

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