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Synthesis, characterization and antitumor activity of palladium(II) complexes of imidazolidine-2-thione

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Abstract

Complexes of the type cis-[PdX2(imzt)(PPh3)] {imzt = imidazolidine-2-thione; PPh3 = triphenylphosphine; X = Cl (1), Br (2), I (3), SCN (4)} have been synthesized and characterized by elemental analyses, molar conductance, IR and 1H NMR spectroscopies. The complex 1·MeOH was obtained from the reaction of [PdCl2(CH3CN)2], imidazolidine-2-thione and triphenylphosphine in CHCl3/CH3OH. Complexes 2·MeOH, 3 and 4 were prepared by metathesis of the chlorido ligands in 1 with bromide, iodide and thiocyanate, respectively. Elemental analyses showed good agreement with the expected mononuclear compositions, while the molar conductivities of the complexes in DMF were consistent with their nonelectrolytic nature. NMR spectra confirmed coordination of the imidazolidine-2-thione and triphenylphosphine ligands. Single-crystal X-ray diffraction determination of 1·CH3OH showed that the coordination geometry around PdII is nearly square planar, with the chlorido ligands in a cis configuration. All four complexes have been tested in vitro by XTT assay for their cytotoxicity against human glioblastoma cell line (U87MG). The binding of 1 with guanosine was studied by 1H NMR spectroscopy, revealing that the coordination takes place via N7.

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Acknowledgements

This work was sponsored by Grants from FAPESP (proc. 2009/54011-8, 2012/15486-3 and 2016/17711-5), FAPEMIG, CNPq (proc. 475322/2009-6 and 422105/2016-3) and CAPES.

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Authors and Affiliations

  1. Departamento de Química Geral e Inorgânica, Instituto de Química de Araraquara, UNESP – Univ Estadual Paulista, P.O. Box 355, Araraquara, São Paulo, 14801–970, Brazil

    Thales R. de Moura, Sahra L. Cavalcanti, Antonio E. Mauro & Adelino V. G. Netto

  2. Departamento de Biologia, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, USP Av. Bandeirantes 3900, Ribeirão Prêto, São Paulo, 14040-901, Brazil

    Paulo R. D. V. de Godoy & Elza T. Sakamoto-Hojo

  3. Departamento de Química, Universidade Federal de São Carlos, São Carlos, São Paulo, CEP 13.565-905, Brazil

    Fillipe V. Rocha

  4. Instituto de Química, UNIFAL - MG - Univ Federal de Alfenas, Alfenas, Minas Gerais, 37130-000, Brazil

    Eduardo T. de Almeida

  5. Instituto de Química de São Carlos, Universidade de São Paulo, Avenida Trabalhador São-carlense, 400, São Carlos, São Paulo, CEP 13566-590, Brazil

    Victor M. Deflon

Authors
  1. Thales R. de Moura
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  2. Sahra L. Cavalcanti
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  3. Paulo R. D. V. de Godoy
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  4. Elza T. Sakamoto-Hojo
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  5. Fillipe V. Rocha
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  6. Eduardo T. de Almeida
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  7. Victor M. Deflon
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  8. Antonio E. Mauro
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  9. Adelino V. G. Netto
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Corresponding authors

Correspondence to Thales R. de Moura or Adelino V. G. Netto.

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de Moura, T.R., Cavalcanti, S.L., de Godoy, P.R.D.V. et al. Synthesis, characterization and antitumor activity of palladium(II) complexes of imidazolidine-2-thione. Transit Met Chem 42, 565–574 (2017). https://doi.org/10.1007/s11243-017-0161-9

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  • DOI: https://doi.org/10.1007/s11243-017-0161-9

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