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Two Cu(I) complexes based on semicarbazone ligand: synthesis, crystal structure, Hirshfeld surface and anticancer activity evaluation against human cell lines

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Abstract

Two novel Cu(I) complexes with the 2-acetylpyridine-N(4)-phenyl semicarbazone (HL) ligand, [CuCl (HL)(PPh3)]∙CH3CN (1) and [CuBr (HL)(PPh3)] (2), were investigated by single-crystal X-ray analysis, Hirshfeld surface, and physicochemical and spectroscopic methods. In both cases, the Schiff base was coordinated by the bidentate ligand via the pyridine nitrogen and the iminic nitrogen atoms. A molecule of triphenylphosphine and a halide ion (Cl− or Br−) completed the coordination sphere of the metal centers. The geometry around the copper atoms was distorted tetrahedral geometry. The secondary coordination sphere of Cu(I) is pentacoordinated and has weak interactions Cu···O of 2.906(1) Å and 2.783(1) Å. The 3D Hirshfeld surface and the 2D fingerprint plots of the complexes were analyzed quantitatively to verify the presence of intermolecular interactions. By their crystal structure of (2), it is possible to observe π···π stacking interactions between the pyridyl and phenyl rings from HL and also between phenyl rings and the triphenylphosphine ligands forming a 1D network. The biological activity of the Cu(I) salts, the free semicarbazone, and its Cu(I) complexes was evaluated against human cancer cell lines MCF-7 and nontumor cell lines PBMC.

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Acknowledgments

All funding agencies are acknowledged for partial financial support.

Funding sources

The authors wish to thank FAPDF (process number 0193.001545/2017). This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior—Brasil (CAPES)—Finance Code 001, FINEP/CTINFRA, CNPq and DPP-UnB.

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Authors and Affiliations

  1. Laboratory of Inorganic Synthesis and Crystallography, University of Brasilia (IQ-UnB), Campus Universitário Darcy Ribeiro, Brasilia, DF, CEP 70904-970, Brazil

    Pedro H. O. Santiago, Marcio A. S. Chagas & Claudia C. Gatto

  2. Institute of Biological and Health Science, Federal University of Mato Grosso, Barra do Garças, CEP 78600-000, Brazil

    Mahmi Fujimori, Eduardo L. França & Adenilda C. Honorio-França

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  1. Pedro H. O. Santiago
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  2. Mahmi Fujimori
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  3. Marcio A. S. Chagas
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The manuscript was written with contributions from all authors. All authors have approved the final version of the manuscript.

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Correspondence to Claudia C. Gatto.

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Crystallographic data for the structures in this work have been deposited to the Cambridge Crystallographic Data Centre, CCDC 1893403-1893404. Copies of the available material can be obtained free of charge by application to the Director, CCDC, 12 Union Road, Cambridge CH2 1EZ, UK (Fax: +441,223 336,033; E-mail: deposit@ccdc.cam.ac.uk or http://www.ccdc.cam.ac.uk). Crystallographic data are in CIF files.

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Santiago, P.H.O., Fujimori, M., Chagas, M.A.S. et al. Two Cu(I) complexes based on semicarbazone ligand: synthesis, crystal structure, Hirshfeld surface and anticancer activity evaluation against human cell lines. Struct Chem 31, 171–180 (2020). https://doi.org/10.1007/s11224-019-01379-w

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