Skip to main content
SpringerLink
Log in

trans-Platinum Complexes with Diclofenac, Aspirin, and 2,6-Di-tert-Butylphenol Fragment: Synthesis and Biological Activity

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

Abstract

A series of σ-aryl platinum complexes with the sterically hindered phenol group of the general formula RPt[PPh3]2X (R = 3,5-di-tert-butyl-4-hydroxyphenyl; X = Cl (I), diclofenac (II), aspirin (III), and OOCR (IV)) is synthesized and characterized by 1H, 13C, and 31P NMR spectroscopy, IR spectroscopy, and elemental analysis. The molecular structure of compound I is determined by X-ray diffraction (XRD) (CIF file CCDC no. 2243100). The electron and hydrogen atom transfers are studied by spectrophotometry in the CUPRAC and DPPH tests. Complexes I, II, and IV are active reducing agents of Cu(II). The antioxidant activity is studied as the ability of the compounds to inhibit lipoxygenase (LOX-1B). Compound I is found to be an inhibitor of LOX-1B. The antiproliferative properties of the complexes are studied in vitro on the HCT-116, MCF-7, and A-549 cancer cells and WI-38 normal cells. The synthesized compounds have a lower antiproliferative activity than that of 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.

Similar content being viewed by others

REFERENCES

  1. Guddneppanavar, R., Saluta, G., Kucera, G.L., and Bierbach, U., J. Med. Chem., 2014, vol. 49, no. 11, p. 3204.

    Article  Google Scholar 

  2. Kelland, L.R., Barnard, F.G.C., Mellish, K.J., and Jones, M., Cancer Res., 1994, vol. 8, p. 5618.

    Google Scholar 

  3. Cheng, Q., Wang, H., Min, Y., and Wang, J., Chem. Commun., 2014, vol. 50, p. 7427.

    Article  CAS  Google Scholar 

  4. Hager, S., Ackermann, C.J., Joerger, M., et al., Annals Oncology, 2016, vol. 27, p. 975.

    Article  CAS  Google Scholar 

  5. Intini, F.P., Zajac, J., Novohradsky, V., et al., Inorg. Chem., 2017, vol. 56, no. 3, p. 1483.

    Article  CAS  PubMed  Google Scholar 

  6. Ayoub, S.S., Botting, R.M., Joshi, A.N., et al., Mol. Cell. Biochem., 2009, vol. 327, nos. 1–2, p. 101.

    Article  CAS  PubMed  Google Scholar 

  7. D’Autreaux, B. and Toleda, M.B., Nat. Rev. Mol. Cell Biol., 2007, vol. 8, no. 10, p. 813.

    Article  PubMed  Google Scholar 

  8. Sies, H., Berndt, C., and Jones, D.P., Annu. Rev. Biochem., 2017, vol. 86, p. 715.

    Article  CAS  PubMed  Google Scholar 

  9. Antonenko, T.A., Shpakovsky, D.B., Vorobyov, M.A., et al., Appl. Organomet. Chem., 2018, vol. 32, р. e4381.

  10. Antonenko, T.A., Gracheva, Yu.A., Shpakovsky, D.B., et al., Int. J. Mol. Sci., 2023, vol. 24, p. 2024.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Brauer, G., Handbook of Preparative Inorganic Chemistry, New York: Academic, 1983, vol. 5, р. 1814.

    Google Scholar 

  12. Milaev, A.G., Panov, V.B., and Okhlobystin, O.Yu., Zh. Obshch. Khim., 1981, vol. 51, no. 12, p. 2715.

    CAS  Google Scholar 

  13. Malatesta, L. and Cariello, C., J. Chem. Soc., 1958, no. 6, p. 2323.

  14. Milaeva, E.R., Rubezhov, A.Z., Prokoph’ev, A.I., and Okhlobystin, O.Yu., J. Organomet. Chem., 1980, vol. 188, no. 3, p. 43.

    Article  Google Scholar 

  15. Krause, L., Herbst-Irmer, R., Sheldrick, G.M., and Stalke, D., J. Appl. Crystallogr., 2015, vol. 48, p. 3.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Sheldrick, G.M., Acta Crystallogr., Sect. A: Found. Adv., 2015, vol. 71, p. 3.

    Article  Google Scholar 

  17. Sheldrick, G.M., Acta Crystallogr., Sect. C: Struct. Chem., 2015, vol. 71, p. 3.

    Article  Google Scholar 

  18. Apak, R., Guglu, K., Ozyurek, M., and Karademir, S., J. Agric. Food Chem., 2004, vol. 52, p. 7970.

    Article  CAS  PubMed  Google Scholar 

  19. Brand-Williams, W., Cuvelier, M.E., and Berset, C., Food Sci. Technol., 1995, vol. 28, p. 25.

    CAS  Google Scholar 

  20. Ozturk, I., Filimonova, S., and Hadjikakou, S.K., Inorg. Chem., 2010, no. 7, p. 488.

  21. Niks, M. and Otto, M., J. Immunol. Methods, 1990, vol. 130, no. 1, p. 149.

    Article  CAS  PubMed  Google Scholar 

  22. Ustafa, M.O., Agric. Food Chem., 2004, vol. 52, p. 7970.

    Article  Google Scholar 

Download references

Funding

This work was supported by the Russian Science Foundation, project no. 22-63-00016.

Author information

Authors and Affiliations

  1. Moscow State University, Moscow, Russia

    T. A. Antonenko, D. B. Shpakovskii, Yu. A. Gracheva, K. A. Lysenko & E. R. Milaeva

Authors
  1. T. A. Antonenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. B. Shpakovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. A. Gracheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. K. A. Lysenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. E. R. Milaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to T. A. Antonenko.

Ethics declarations

The authors of this work declare that they have no conflicts of interest.

Additional information

Translated by E. Yablonskaya

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Antonenko, T.A., Shpakovskii, D.B., Gracheva, Y.A. et al. trans-Platinum Complexes with Diclofenac, Aspirin, and 2,6-Di-tert-Butylphenol Fragment: Synthesis and Biological Activity. Russ J Coord Chem 49, 652–659 (2023). https://doi.org/10.1134/S1070328423600511

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070328423600511

Keywords:

Search

Navigation