Skip to main content
SpringerLink
Log in

Synthesis, Structure, and Antiproliferative Activities of Complexes of Some Transition Metals with 5,7-Dichloro-8-Hydroxyquinoline-2-Carboxaldehyde-4-Phenyl-3-Thiosemicarbazone

  • Published:
Pharmaceutical Chemistry Journal Aims and scope

A new quinoline–thiosemicarbazone derivative, 5,7-dichloro-8-hydroxyquinoline-2-carboxaldehyde-4-phenyl-3-thiosemicarbazone (QPS) and seven complexes of QPS with d-transition metals (Mn, Fe, Co, Ni, Cu, Zn, Cd) were successfully synthesized. Spectrometry methods such as IR, ESI-MS, and 1H NMR were utilized to determine the structure of complexes that almost all complexes form the metal:ligand ratio of 1:1, except for FeQPS, which forms a 1:2 ratio. The center metals bond to QPS through O, Nquinoline and Nthiosemicarbazone. Four tested complexes (MnQPS, CoQPS, NiQPS, CuQPS) show medium inhibition to KB and Hep-G2 cancer cell lines. ZnQPS has the high activity against KB and Hep-G2 (IC50 = 13.51 and 10.28 μg/mL) and a high impact against the LU cancer cell line (IC50 = 2.0 μg/mL). CdQPS complexes showed excellent activity on both KB and Hep-G2 with IC50 very low, IC50 = 3.12 and 3.06 μg/mL, which is much lower than cisplatin.

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.

Similar content being viewed by others

References

  1. V. Cepeda, M. A. Fuertes, J. Castilla, et al., Anti-Canc. Agents Med. Chem., 7(1), 3 – 18 (2007).

    CAS  Google Scholar 

  2. R. Oun, Y. E. Moussa and N. J. Wheate, Dalton Trans., 47, 6645 – 6653 (2018).

    Article  CAS  PubMed  Google Scholar 

  3. T. C. Johnstone, K. Suntharalingam, S. J. Lippard., Chem. Rev., 116(5), 3436 – 3486 (2016).

  4. C. Molinaro, A. Martoriati, L. Pelinski, and K. Cailliau, Cancers, 12(10), 2863 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. L. T. H. Hai, N. T. N. Vinh, L. T. Tuyen, et al., J. Coord. Chem., 72(10), 1637 – 1651 (2019).

    Article  CAS  Google Scholar 

  6. N. T. Chi, T. T. C. Mai, P. V. Thong, et al., Acta Cryst., Sec. C, 73(11), 1030 – 1037 (2017).

  7. H. R. Zhang, Y. C. Liu, Z. F. Chen, et al., Russ. J. Coord. Chem., 44(5), 322 – 333, (2018).

    Article  CAS  Google Scholar 

  8. Q. Y. Yang, Q. Q. Cao, Q. P. Qin, et al., Int. J. Mol. Sci., 19(7), 1874 (2018).

    Article  PubMed  PubMed Central  Google Scholar 

  9. T. Meng, Q. P. Qin, H. H. Zou, et al., ACS Med. Chem. Lett., 10, 1603 – 1608 (2019).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. K. Avinash, K. Vinaya, N. Krishna, et al., Bio-org. Chem., 112, 104962 (2021).

    Google Scholar 

  11. C. Santini, M. Pellei, V. Gandin, et al., Chem. Rev., 114(1), 815 – 862 (2014).

    Article  CAS  PubMed  Google Scholar 

  12. D. Rogolino, A. Cavazzoni, A. Gatti, et al., Eur. J. Med. Chem., 128, 140 – 153 (2017).

    Article  CAS  PubMed  Google Scholar 

  13. F. Bisceglie, A. Musiari, S. Pinelli, R. Alinovi, et al., J. Inorg. Biochem., 152, 10 – 19 (2015).

    Article  CAS  PubMed  Google Scholar 

  14. E. Ramachandran, V. Gandin, R. Bertani, et al., Molecules, 25, 1868 (2020).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. S. H. Chan, C. H. Chui, S. W. Chan, ACS Med. Chem. Lett., 4(2), 170 – 174 (2013).

    CAS  Google Scholar 

  16. M. Tim, M., J. Imm. Meth., 65, 55 – 63 (1983).

  17. D. A. Scudiero, R. H. Shoemaker, K. D. Paull, et al., Canc. Res., 48, 4827 – 4833 (1988).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Chemistry, Hanoi National University of Education, Vietnam, 123000, Hanoi, Cau Giay, Xuan Thuy st., 136

    Pham Thi Hai Linh, Mai Phuong Chi, Le Phuong Thao & Le Thi Hong Hai

  2. Faculty of Natural Science and Technology, Tay Nguyen University, Vietnam, 630000, Dak Lak, Buon Ma Thuot, Le Duan st., 567

    Ninh Thi Minh Giang

Authors
  1. Pham Thi Hai Linh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mai Phuong Chi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Le Phuong Thao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ninh Thi Minh Giang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Le Thi Hong Hai
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Le Thi Hong Hai.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Linh, P.T.H., Chi, M.P., Thao, L.P. et al. Synthesis, Structure, and Antiproliferative Activities of Complexes of Some Transition Metals with 5,7-Dichloro-8-Hydroxyquinoline-2-Carboxaldehyde-4-Phenyl-3-Thiosemicarbazone. Pharm Chem J 57, 1593–1598 (2024). https://doi.org/10.1007/s11094-024-03053-w

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-024-03053-w

Keywords

Search

Navigation