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Copper (II) complexes with N, S donor pyrazole-based ligands as anticancer agents

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Abstract

A group of bidentate nitrogen and sulfur donor pyrazole derivative ligands abbreviated as Na[RNCS(Pz)], Na[RNCS(PzMe2)], Na[RNCS(PzMe3)], Na[RNCS(PzPhMe)], Na[RNCS(PzPh2)], where (R = Et, Ph), and their Cu (II) complexes were synthesized and characterized by spectroscopic and physicochemical methods. The crystal structure of [Cu(PhNCSPzMe3)2] was determined by X-ray crystallography analysis and the results described a distorted square planar coordination geometry for this complex. Also, the cyclic voltammetry investigations indicated that the synthesized copper complex is an electrochemically active species. Moreover, the cytotoxic activity of all of the twenty synthesized compounds was evaluated using MTT assay against the MCF-7 (human breast carcinoma) cell lines, in vitro. Cu (II) complexes indicate significant cytotoxicity against the MCF-7 cell lines as compared with the free ligands. The docking studies showed that the copper complexes have better interactions with EGFR and CDK2 proteins, compared to the free ligands, and most of the studied compounds have a higher value of binding energy relative to the studied controls. The results of QSAR analysis suggest that dipole moment is in direct correlation with the obtained IC50 values, and it strongly impact the anticancer effects generated by the compounds. Our findings suggest that the developed copper complexes can be good candidates for further evaluations as chemotherapeutic agents in the treatment of cancer.

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Acknowledgements

We would like to thank University of Azarbaijan Shahid Madani for supporting this work. Single crystal X-ray diffraction experiments were performed at the University of Akron. The optimization of the structure of the compounds were performed in the Molecular Simulation laboratory of Azarbaijan Shahid Madani University. We thank them for their helpful collaboration.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Basic Science, Azarbaijan Shahid Madani University, P. O. Box 53714-161, Tabriz, Iran

    Monireh Ghorbanpour, Behzad Soltani, Jaber Jahanbin Sardroodi & Rahim Mohammad-Rezaei

  2. Department of Clinical Biochemistry and Laboratory Medicine, Faculty of Medicine, Tabriz University of Medical Sciences, Tabriz, Iran

    Ali Mota

  3. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran

    Elnaz Mehdizadeh Aghdam & Ommoleila Molavi

  4. Molecular Medicine Research Center, Biomedicine Institute, Tabriz University of Medical Sciences, Tabriz, Iran

    Elnaz Mehdizadeh Aghdam

  5. Pharmaceutical Analysis Research Center, Tabriz University of Medical Sciences, Tabriz, Iran

    Ali Shayanfar

  6. Department of Biology, Faculty of Basic Sciences, Azarbaijan Shahid Madani University, Tabriz, Iran

    Mostafa Ebadi-Nahari

  7. Department of Chemistry, University of Akron, Akron, OH, 44325, USA

    Christopher J. Ziegler

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  1. Monireh Ghorbanpour
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Appendix: supplementary data

CCDC 2059101 contain the supplementary crystallographic data for 18. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

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Ghorbanpour, M., Soltani, B., Mota, A. et al. Copper (II) complexes with N, S donor pyrazole-based ligands as anticancer agents. Biometals 35, 1095–1111 (2022). https://doi.org/10.1007/s10534-022-00426-0

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