Copper(II) complexes with pyridoxal dithiocarbazate and thiosemicarbazone ligands: crystal structure, spectroscopic analysis and cytotoxic activity

  • Claudia C. GattoEmail author
  • Marcio A. S. Chagas
  • Iariane J. Lima
  • Francyelli Mello Andrade
  • Hugo D. Silva
  • Gabrielly R. Abrantes
  • Elisângela P. S. Lacerda


The present study reports the synthesis and crystal structures of Cu(II) complexes with pyridoxal S-allyldithiocarbazate (H2L1) and pyridoxal thiosemicarbazones (H2L2 = pyridoxal-N4-phenyl-3-thiosemicarbazone and H2L3 = pyridoxal-N4-semicarbazone). The single-crystal X-ray study reveals that in all cases, the Schiff base coordinated tridentately through the ONS-donor atoms, resulting in distorted square planar coordination geometries with the copper atoms. The Cu(II) complexes with pyridoxal dithiocarbazate, [Cu(HL1)Cl]·H2O and [Cu(HL1)Br]·H2O, as well as three complexes with pyridoxal thiosemicarbazone, [Cu(HL2)Cl]·dmf, [Cu(HL2)Br]·H2O·dmf and [Cu(H2L3)Br]Br·H2O, were also characterized by spectroscopic and physical–chemical analyses. The cytotoxicity of the complexes toward two kinds of cancerous cells (Ehrlich and S-180 cells) was evaluated by an MTT assay. The complex [Cu(H2L3)Br]Br·H2O was selected to study both the cellular and molecular mechanisms underlying its promising cytotoxicity. The Hoechst 33342/PI dual-staining assay showed the typical apoptotic morphology of cancer cells, and the RT-qPCR analysis revealed that the expressions of Bax, Casp3, Casp8, Casp9 and TP53 were markedly increased in both the Ehrlich and S-180 cells exposed to 10 μM for 3 h. According to our results, this complex induces cell death through apoptosis, showing potential as a future drug against cancer.

Graphical abstract

Five stable copper(II) complexes with pyridoxal have been synthesized and their crystal structure has been studied. Spectroscopy experiments and cytotoxic assays against S-180 and Ehrlich cancer cell lines were performed and showed promising results as novel antitumor drugs.



We gratefully acknowledge the financial support of FAPDF, CAPES, CNPq and FINEP/CTINFRA.


Funding was provided by Fundação de Apoio à Pesquisa do Distrito Federal Funda de Apoio? Pesquisa do Distrito Federal (Grant No. 0193.001545/2017).

Supplementary material

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Supplementary material 1 (DOCX 1274 kb)


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Copyright information

© Springer Nature Switzerland AG 2019

Authors and Affiliations

  • Claudia C. Gatto
    • 1
    Email author
  • Marcio A. S. Chagas
    • 1
  • Iariane J. Lima
    • 1
  • Francyelli Mello Andrade
    • 2
  • Hugo D. Silva
    • 2
    • 3
  • Gabrielly R. Abrantes
    • 2
  • Elisângela P. S. Lacerda
    • 2
  1. 1.Laboratory of Inorganic Synthesis and CrystallographyUniversity of Brasilia (IQ-UnB)BrasíliaBrazil
  2. 2.Laboratory of Molecular Genetics and CytogeneticsFederal University of GoiásGoiâniaBrazil
  3. 3.University Centre of Goiás (Centro Universitário de Goiás - Uni- ANHANGÜERA)GoiâniaBrazil

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