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

  • Pedro H. O. Santiago
  • Mahmi Fujimori
  • Marcio A. S. Chagas
  • Eduardo L. França
  • Adenilda C. Honorio-França
  • Claudia C. GattoEmail author
Original Research


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.


Copper(I) complexes Semicarbazone Crystal structure Hirshfeld surface Cytotoxicity 



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.

Author contributions

The manuscript was written with contributions from all authors. All authors have approved the final version of the manuscript.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflicts of interest.

Supplementary material

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ESM 1 (CIF 964 kb)
11224_2019_1379_MOESM2_ESM.cif (1.1 mb)
ESM 2 (CIF 1110 kb)


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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Laboratory of Inorganic Synthesis and CrystallographyUniversity of Brasilia (IQ-UnB)BrasiliaBrazil
  2. 2.Institute of Biological and Health ScienceFederal University of Mato GrossoBarra do GarçasBrazil

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