Skip to main content
SpringerLink
Log in

Novel cinobufagin oxime ether derivatives as potential Na+/K+-ATPase inhibitors: Synthesis, biological screening and molecular docking

  • Published:
Chemical Research in Chinese Universities Aims and scope

Abstract

Some cinobufagin oxime ether derivatives as potential Na+/K+-ATPase inhibitors were synthesized by following the side chain of istaroxime. These compounds inhibit Na+/K+-ATPase in a dose-dependent manner. Compound 3c with an oxyethylamine side chain that is the same as that of istaroxime showed the most potent inhibition, which was stronger than compound 3a with only hydroxyoxime moiety at C-3 and compound 3b with a methylated hydroxyoxime moiety. Molecular docking was used to explore the binding modes of the target compounds with Na+/K+-ATPase, which suggested that the longer ethyl amine group at C-3 oxime moiety of compound 3c could make stronger interaction with Na+/K+-ATPase via intermolecular charge-charge and H-bond interaction as compared with other derivatives.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Skou J. C., Angew. Chem. Int. Ed., 1998, 37, 2320

    Article  CAS  Google Scholar 

  2. Kaplan J. H., Annu. Rev. Biochem., 2002, 71, 511

    Article  CAS  Google Scholar 

  3. Laursen M., Gregersen J. L., Yatime L., Nissen P., Fedosova N. U., P. Natl. Acad. Sci. USA, 2015, 112, 1755

    Article  CAS  Google Scholar 

  4. Bavishi C., Khan A. R., Ather S., Int. J. Cardiol., 2015, 188, 99

    Article  Google Scholar 

  5. Li Z., Xie Z., Pfluügers Arch, 2009, 457, 635

    Article  CAS  Google Scholar 

  6. Prassas I., Diamandis E. P., Nat. Rev. Drug Discov., 2008, 7, 926

    Article  CAS  Google Scholar 

  7. Tian H. Y., Wang L., Zhang X. Q., Zhang D. M., Wang Y., Jiang R. W., Ye W. C., Steroids, 2010, 75, 884

    Article  CAS  Google Scholar 

  8. Tian H. Y., Wang L., Zhang X. Q., Wang Y., Zhang D. M., Jiang R. W., Liu Z., Liu J. S., Li Y. L., Ye W. C., Chem. Eur. J., 2010, 16, 10989

    Article  CAS  Google Scholar 

  9. Tian H. Y., Luo S. L., Liu J. S., Wang L., Wang Y., Zhang D. M., Zhang X. Q., Jiang R. W., Ye W. C., J. Nat. Prod., 2013, 76, 1842

    Article  CAS  Google Scholar 

  10. Li B. J., Tian H. Y., Zhang D. M., Lei Y. H., Wang L., Jiang R. W., Ye W. C., Fitoterapia, 2015, 105, 7

    Article  CAS  Google Scholar 

  11. Tian H. Y., Zhang P. W., Liu J. S., Zhang D. M., Zhang X. Q., Jiang R. W., Ye W. C., Chin. Chem. Lett., 2014, 25, 1104

    Article  CAS  Google Scholar 

  12. Cheng W., Tan Y. F., Tian H. Y., Gong X. W., Chen K. L., Jiang R. W., Nat. Prod. Res., 2014, 28, 901

    Article  CAS  Google Scholar 

  13. Zhang R. R., Tian H. Y., Tan Y. F., Chung T. Y., Sun X. H., Xia X., Ye W. C., Middleton D. A., Fedosova N., Esmann M., Tzen J. T. C., Jiang R. W., Org. Biomol. Chem., 2014, 12, 8919

    Article  CAS  Google Scholar 

  14. Tian H. Y., Yuan X. F., Jin L., Li J., Luo C., Ye W. C., Jiang R. W., Chem. Biol. Interact., 2014, 207, 16

    Article  CAS  Google Scholar 

  15. Zhang P. W., Tang H. J., Tian H. Y., Zhang R. R., Jiang R. W., Chin. J. Struct. Chem., 2014, 33, 1123

    CAS  Google Scholar 

  16. Gobbini M., Armaroli S., Banfi L., Benicchio A., Carzana G., Fe-drizzi G., Ferrari P., Giacalone G., Giubileo M., Marazzi G., Miche-letti R., Moro B., Pozzi M., Scotti P. E., Torri M., Cerri A., J. Med. Chem., 2008, 51, 4601

    Article  CAS  Google Scholar 

  17. Aditya S., Rattan A., J. Pharmacol. Pharmacother., 2012, 3, 353

    Article  CAS  Google Scholar 

  18. Meng Q., Yau L. F., Lu J. G., Wu Z. Z., Zhang B. X., Wang J. R., Jiang Z. H., J. Ethnopharmacol., 2016, 187, 74

    Article  CAS  Google Scholar 

  19. Hirai Y., Morishita S., Ito C., Sakanashi M., Nihon Yakurigaku Zasshi, 1992, 100, 127

    Article  CAS  Google Scholar 

  20. Wang Z. J., Sun L., Heinbockel T., PLoS One, 2014, 9, e113272

    Article  Google Scholar 

  21. Zhang G., Wang C., Sun M., Li J., Wang B., Jin C., Hua P., Song G., Zhang Y., Nguyen L. L., Cui R., Liu R., Wang L., Zhang X., Onco-target, 2016, 7, 28935

    Google Scholar 

  22. Li P., Song Q., Liu T., Wu Z., Chu X., Zhang X., Zhang Y., Gao Y., Zhang J., Chu L., Scientific World Journal, 2014, 2014, 496705

    Google Scholar 

  23. Hao S., Bao Y. M., An L. J., Cheng W., Zhao R. G., Bi J., Wang H. S., Sun C. S., Liu J. W., Jiang B., Toxicol. in Vitro, 2011, 25, 1644

    Article  CAS  Google Scholar 

  24. Zhang Z., Li Z., Tian J., Jiang W., Wang Y., Zhang X., Li Z., You Q. D., Shapiro J. I., Si S., Xie Z., Mol. Pharmacol., 2010, 77, 961

    Article  CAS  Google Scholar 

  25. Xie Z., Wang Y., Liu G., Zolotarjova N., Periyasamy S. M., Askari A., Arch. Biochem. Biophys., 1996, 330, 153

    Article  CAS  Google Scholar 

  26. Brooks B. R., Bruccoleri R. E., Olafson B. D., States D. J., Swami-nathan S., Karplus M., J. Comp. Chem., 1983, 4, 187

    Article  CAS  Google Scholar 

  27. Dixon S. L., Jr. Merz K. M., J. Med. Chem., 2001, 44, 3795

    Article  CAS  Google Scholar 

  28. He X. J., Tang J. S., Qiao A. M., Wang G. H., Jiang M. M., Liu R. H., Yao X. S., Steroids, 2006, 71, 392

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Pharmacy, Jinan University, Guangzhou, 510632, P. R. China

    Guangping Liang, Jinhua Guo, Rongrong Zhang, Wei Xü & Renwang Jiang

  2. Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, 510632, P. R. China

    Guangping Liang, Jinhua Guo, Rongrong Zhang, Wei Xü & Renwang Jiang

  3. Graduate Institute of Biotechnology, ‘National Chung-Hsing University’, Taichung, 40227, China

    Tseyu Chung & Jason T. C. Tzen

Authors
  1. Guangping Liang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tseyu Chung
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jinhua Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Rongrong Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Wei Xü
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jason T. C. Tzen
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Renwang Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Jason T. C. Tzen or Renwang Jiang.

Additional information

Supported by the National Natural Science Foundation of China(No.81573315), the Guangdong Natural Science Fund, China(No.2015A030313313) and the Guangzhou Industry-University Collaborative Innovation Major Projects, China(No. 201508030016).

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liang, G., Chung, T., Guo, J. et al. Novel cinobufagin oxime ether derivatives as potential Na+/K+-ATPase inhibitors: Synthesis, biological screening and molecular docking. Chem. Res. Chin. Univ. 33, 378–383 (2017). https://doi.org/10.1007/s40242-017-6487-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40242-017-6487-1

Keywords

Search

Navigation