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

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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(sLex) with selectivity over other Lewis sugars, and could significantly stain sLex-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 sLex selectivity and higher binding affinity.

Keywords

Lewis sugar Bisboronic acid Anthracene-based fluorescent probe Biochemical recognition 

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Acknowledgements

We also thanks Professor WANG Binghe(Georgia State University, USA) for his help in revising the manuscript.

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Copyright information

© Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental ScienceHebei UniversityBaodingP. R. China
  2. 2.College of ScienceAgricultural University of HebeiBaodingP. R. China
  3. 3.Department of Chemistry and Center for Diagnostics and TherapeuticsGeorgia State UniversityAtlantaUSA

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