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

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Chemical Research in Chinese Universities Aims and scope

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.

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References

  1. Sun X., Zhai W., Fossey J. S., James T. D., Chem. Commun. 2016, 52, 3456

    Article  CAS  Google Scholar 

  2. Dai C. F., Sagwal A., Cheng Y. F., Peng H. J., Chen W. X., Wang B. H., Pure Appl. Chem. 2012, 84, 2479

    Article  CAS  Google Scholar 

  3. Yang W., Gao S., Gao X., Karnati V. R., Ni W., Wang B., Hooks W. B., Carson J., Weston B. Bioorg. Med. Chem. Lett., 2002, 12, 2175

    Article  CAS  PubMed  Google Scholar 

  4. Dai C., Cazares L. H., Wang L., Chu Y., Wang S. L., Troyer D. A., Semmes O. J., Drake R. R., Wang B., Chem. Commun. 2011, 47, 10338

    Article  CAS  Google Scholar 

  5. Chu Y., Wang D. Z., Wang K., Liu Z. R., Weston B., Wang B. H., Bioorg. Med. Chem. Lett. 2013, 23, 6307

    Article  CAS  PubMed  Google Scholar 

  6. Sun X. L., Zhu B., Ji D. K., Chen Q. B., He X. P., Chen G. R., James T. D., ACS Appl. Mater. Interfaces, 2014, 6, 10078

    Article  CAS  PubMed  Google Scholar 

  7. Guo S., Chen J., Cai B. Y., Chen W. W., Li Y. F., Sun X. L., Chen G. R., He X. P., James T. D., Mater. Chem. Front. 2017, 1, 61

    Article  CAS  Google Scholar 

  8. Yang W., Fan H., Gao S., Gao X., Ni W., Karnati V., Hooks W. B., Carson J., Weston B., Wang B., Chem. Biol. 2004, 11, 439

    Article  CAS  PubMed  Google Scholar 

  9. Xu X. D., Cheng H., Chen W. H., Cheng S. X., Zhuo R. X., Zhang X. Z., Sci. Rep. 2013, 3, 2679

    Article  PubMed  PubMed Central  Google Scholar 

  10. Craig S., Bioorg. Chem. 2012, 40, 137

    Article  CAS  PubMed  Google Scholar 

  11. Gao X., Zhu M., Fan H., Yang W., Karnati V. V. R., Gao S., Carson J., Weston B., Wang B., Bioorg. Med. Chem. Lett. 2015, 25, 2501

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Wang Y., Rong R., Chen H., Zhu M., Wang B., Li X., Bioorg. Med. Chem. Lett. 2017, 27, 1983

    Article  CAS  PubMed  Google Scholar 

  13. Lin Y. I., Lang S. A., Seifert C. M., Child R. G., Morton G. O., Fabio P. F., J. Org. Chem., 1979, 44, 4701

    Article  CAS  Google Scholar 

  14. Cambridgesoft, ChemDraw Professional 2016, 2016

    Google Scholar 

  15. Bowers K. J., Chow D. E., Xu H., Dror R. O., Eastwood M. P., Gregersen B. A., Klepeis J. L., Kolossvary I., Moraes M. A., Sacer-doti F. D., SC 2006 Conference, Proceedings of the ACM/IEEE, IEEE, New York, 2006, 43

    Google Scholar 

  16. Shaw D. E., Research, Desmond Molecular Dynamics System, New York, 2016

    Google Scholar 

  17. Schrödinger, Maestro-Desmond Interoperability Tools, New York, 2016

    Google Scholar 

  18. Larkin J. D., Frimat K. A., Fyles T. M., Flower S. E., James T. D., New J. Chem., 2010, 34, 2922

    Article  CAS  Google Scholar 

  19. James T. D., Sandanayake K. R. A. S., Shinkai S., Angew. Chem. Int. Ed. Engl. 1994, 33, 2207

    Article  Google Scholar 

  20. James T. D., Sandanayake K. R. A. S., Iguchi R., Shinkai S. J. Am. Chem. Soc., 1995, 117, 8982

    Article  CAS  Google Scholar 

  21. Que E. L., Domaille D. W., Chang C. J., Chem. Rev. 2008, 108, 1517

    Article  CAS  PubMed  Google Scholar 

  22. Vendrell M., Zhai D., Er J. C., Chang Y. T., Chem. Rev. 2012, 112, 4391

    Article  CAS  PubMed  Google Scholar 

  23. Su J., Yu M., Lin Z., Zhao H., Liu H., Chem. Res. Chinese Universi-ties 2017, 33(6), 908

    Article  CAS  Google Scholar 

  24. Chang M. H., Chang C. N., Tetrahedron Lett. 2014, 55, 4437

    Article  CAS  Google Scholar 

  25. Tang G., Zhang Y., Zhang Y., Zhou P., Lin Z., Wang Y., Chem. J. Chinese Universities, 2017, 38(11), 2061

    CAS  Google Scholar 

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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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Authors and Affiliations

  1. Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, 071002, P. R. China

    Yan’en Wang, Xueyan Li, Hua Chen & Xiaoliu Li

  2. College of Science, Agricultural University of Hebei, Baoding, 071001, P. R. China

    Yan’en Wang

  3. Department of Chemistry and Center for Diagnostics and Therapeutics, Georgia State University, Atlanta, GA, 30303, USA

    Mengyuan Zhu

Authors
  1. Yan’en Wang
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  2. Xueyan Li
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  3. Hua Chen
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  4. Mengyuan Zhu
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  5. Xiaoliu Li
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Corresponding authors

Correspondence to Hua Chen or Xiaoliu Li.

Additional information

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).

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Wang, Y., Li, X., Chen, H. et al. Synthesis of Bisboronic Acids and Their Selective Recognition of Sialyl Lewis X Antigen. Chem. Res. Chin. Univ. 34, 415–422 (2018). https://doi.org/10.1007/s40242-018-7328-6

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  • DOI: https://doi.org/10.1007/s40242-018-7328-6

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