Skip to main content
SpringerLink
Log in

Synthesis and Antiproliferative Activity of Some New Coumarin Derivatives Derived from 8-Hydroxycoumarin

  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

A new series of coumarin-derived molecules have been synthesized and evaluated for their anticancer activity against human hepatocellular liver carcinoma cell line (HepG2). Compound (IX) showed the least IC50 values in MTT colorimetric assay and significantly inhibited topoisomerase IIβ. DNA flow cytometry assay of compound (IX) revealed cell cycle arrest at G2/M phase and activation of apoptosis as verified by changes in cell cycle kinetics. Further mechanism of apoptosis showed that, compound (IX) induced cell apoptosis probably through the intrinsic mitochondrial pathway of apoptosis. This mechanistic pathway was confirmed by a significant increase in the level of p53, Bax and decrease in the level of Bcl-2 compared to control.

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

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.

Similar content being viewed by others

REFERENCES

  1. Siegel, R.L., Jemal, A., Wender, R.C., Gansler, T., Ma, J., and Brawley, O.W., CA Cancer J. Clin., 2018, vol. 68, pp. 329–339. https://doi.org/10.3322/caac.21460

    Article  PubMed  Google Scholar 

  2. Zhou, F., Shang, W., Yu, X., and Tian, J., Med. Res. Rev., 2018, vol. 38, pp. 741–767. https://doi.org/10.1002/med.21455

    Article  CAS  PubMed  Google Scholar 

  3. Pommier, Y., Leo, E., Zhang, H., Marchand, C., Chem. Biol., 2010, vol. 17, pp. 421–433. https://doi.org/10.1016/j.chembiol.2010.04.012

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Abdelhaleem, E.F., Abdelhameid, M.K., Kassab, A.E., and Kandeel, M.M., Eur. J. Med. Chem., 2018, vol. 143, pp. 1807–1825. https://doi.org/10.1016/j.ejmech.2017.10.075

    Article  CAS  PubMed  Google Scholar 

  5. Nitiss, J.L., Nat. Rev. Cancer, 2009, vol. 9, pp. 338–350. https://doi.org/10.1038/nrc2607

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Wang, N., Zhu, M., Tsao, S.-W., Man, K., Zhang, Z., and Feng, Y., Mol. Cancer, 2013, vol. 12, pp. 119. https://doi.org/10.1186/1476-4598-12-119

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Sudan, S. and Rupasinghe, H.V., Anticancer Res., 2014, vol. 34, pp. 1691–1699. http://ar.iiarjournals.org/content/34/4/1691.abstract.

    CAS  PubMed  Google Scholar 

  8. Elmore, S., Toxicol. Pathol., 2007, vol. 35, pp. 495–516. https://doi.org/10.1080/01926230701320337

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Rashad, M.S., Georgey, H.H., George, R.F., and Abdel-Gawad, N.M., Future Med. Chem., 2018, vol. 10, pp. 1649–1664. https://doi.org/10.4155/fmc-2018-0068

    Article  CAS  PubMed  Google Scholar 

  10. Kim, R., Emi, M., and Tanabe, K., Cancer Biol. Ther., 2005, vol. 4, pp. 924–933. https://doi.org/10.4161/cbt.4.9.2101

    Article  CAS  PubMed  Google Scholar 

  11. Abdelhameid, M.K., Zaki, I., Mohammed, M.R., and Mohamed, K.O., Bioorg. Chem., 2020, vol. 101, pp. 103995–104007. https://doi.org/10.1016/j.bioorg.2020.103995

    Article  CAS  PubMed  Google Scholar 

  12. Zaki, I., Abdelhameid, M.K., El-Deen, I.M., Abdel Wahab, A.H.A., Ashmawy, A.M., and Mohamed, K.O., Eur. J. Med. Chem., 2018, vol. 156, pp. 563–579. https://doi.org/10.1016/j.ejmech.2018.07.003

    Article  CAS  PubMed  Google Scholar 

  13. Liu, Y.-P., Yan, G., Xie, Y.-T., Lin, T.-C., Zhang, W., Li, J., Wu, Y.-J., Zhou, J.-Y., and Fu, Y.-H., Bioorg. Chem., 2020, vol. 97, pp. 103699–103713. https://doi.org/10.1016/j.bioorg.2020.103699

    Article  CAS  PubMed  Google Scholar 

  14. Swain, B., Angeli, A., Singh, P., Supuran, C.T., and Arifuddin, M., Bioorg. Med. Chem., 2020, vol. 28, pp. 115586–115597. https://doi.org/10.1016/j.bmc.2020.115586

    Article  CAS  PubMed  Google Scholar 

  15. Ahmed, E.Y., Abdel Latif, N.A., El-Mansy, M.F., Elserwy, W.S., and Abdelhafez, O.M., Bioorg. Med. Chem., 2020, vol. 28, pp. 115328–115338. https://doi.org/10.1016/j.bmc.2020.115328

    Article  CAS  PubMed  Google Scholar 

  16. Zhang, L. and Xu, Z., Eur. J. Med. Chem., 2019, vol. 181, pp. 111587. https://doi.org/10.1016/j.ejmech.2019.111587

    Article  CAS  PubMed  Google Scholar 

  17. Manolov, I., Maichle-Moessmer, C., and Danchev, N., Eur. J. Med. Chem., 2006, vol. 41, pp. 882–890. https://doi.org/10.1016/j.ejmech.2006.03.007

    Article  CAS  PubMed  Google Scholar 

  18. Wang, J., Lu, M.L., Dai, H.L., Zhang, S.P., Wang, H.X., and Wei, N., Braz. J. Med. Biol. Res., 2015, vol. 48, pp. 245–253. https://doi.org/10.1590/1414-431x20144074

    Article  CAS  PubMed  Google Scholar 

  19. Prasad, K.N., Xie, H., Hao, J., Yang, B., Qiu, S., Wei, X., Chen, F., and Jiang, Y., Food Chem., 2010, vol. 118, pp. 62–66. https://doi.org/10.1016/j.foodchem.2009.04.073

    Article  CAS  Google Scholar 

  20. Hejchman, E., Taciak, P., Kowalski, S., Maciejewska, D., Czajkowska, A., Borowska, J., Śladowski, D., and Młynarczuk-Biały, I., Pharmacol. Rep., 2015, vol. 67, pp. 236–244. https://doi.org/10.1016/j.pharep.2014.09.008

    Article  CAS  PubMed  Google Scholar 

  21. Nasr, T., Bondock, S., and Youns, M., Eur. J. Med. Chem., 2014, vol. 76, pp. 539–548. https://doi.org/10.1016/j.ejmech.2014.02.026

    Article  CAS  PubMed  Google Scholar 

  22. Zhao, P., Chen, L., Li, L.-H., Wei, Z.-F., Tong, B., Jia, Y.-G., Kong, L.-Y., Xia, Y.-F., and Dai, Y., BMC Cancer, 2014, vol. 14, pp. 987–1005. https://doi.org/10.1186/1471-2407-14-987

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. El-Deen, I., Elgareib, M.S., Mahdy, A.R., and Al-Saleem, M.S., Mens Agitat, 2018, vol. 13, pp. 1–5.

    Google Scholar 

  24. Moustafa, A.M.Y. and Bakare, S.B., Res. Chem. Intermed., 2019, vol. 45, pp. 3895–3912. https://doi.org/10.1007/s11164-019-03827-y

    Article  CAS  Google Scholar 

  25. Rahman, A.U., Medrano, M.A., and Mittal, O., Recl. Trav. Chim. Pays-Bas, 1960, vol. 79, pp. 188–192.

    Article  CAS  Google Scholar 

  26. Menezes, J.C. and Diederich, M., Future Med. Chem., 2019, vol. 11, pp. 1057–1082. https://doi.org/10.4155/fmc-2018-0375

    Article  CAS  PubMed  Google Scholar 

  27. Mohamed, K.O., Zaki, I., El-Deen, I.M., and Abdelhameid, M.K., Bioorg. Chem., 2019, vol. 84, pp. 399–409. https://doi.org/10.1016/j.bioorg.2018.12.007

    Article  CAS  PubMed  Google Scholar 

  28. Wei, H., Ruthenburg, A.J., Bechis, S.K., and Verdine, G.L., J. Biolog. Chem., 2005, vol. 280, pp. 37041–37047. https://doi.org/10.1074/jbc.M506520200

    Article  CAS  Google Scholar 

Download references

Funding

This work was funded by the authors.

Author information

Authors and Affiliations

  1. Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Port Said University, Port Said, Egypt

    Islam Zaki

  2. Chemistry Department, Faculty of Science, Port Said University, Port Said, Egypt

    El-Sherbiny H. El-Sayed & Eman M. Radwan

Authors
  1. Islam Zaki
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. El-Sherbiny H. El-Sayed
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Eman M. Radwan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Islam Zaki.

Ethics declarations

COMPLIANCE WITH ETHICAL STANDARDS

This article does not contain any studies involving animals or human participants performed by any of the authors.

Conflict of Interests

The authors report no conflicts of interest.

Supplementary Information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zaki, I., El-Sayed, ES.H. & Radwan, E.M. Synthesis and Antiproliferative Activity of Some New Coumarin Derivatives Derived from 8-Hydroxycoumarin. Russ J Bioorg Chem 47, 514–523 (2021). https://doi.org/10.1134/S106816202102028X

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S106816202102028X

Keywords:

Search

Navigation