Cytotoxicity of platinum(IV) and palladium(II) complexes with meso-1,2-diphenyl-ethylenediamine-N,N'-di-3-propanoic acid. Crystal structure of [Pd(1,2-dpheddp)] complex

Authors

  • Marina Ž Mijajlović Faculty of Medical Sciences, University of Kragujevac
  • Miloš V Nikolić Faculty of Medical Sciences, University of Kragujevac
  • Verica V Jevtić Department of Chemistry, Faculty of Science, University of Kragujevac
  • Zoran R Ratković Department of Chemistry, Faculty of Science, University of Kragujevac
  • Jelena Milovanović Faculty of Medical Sciences, University of Kragujevac
  • Aleksandar Arsenijević Faculty of Medical Sciences, University of Kragujevac
  • Bojana Stojanović Faculty of Medical Sciences, University of Kragujevac
  • Slađana B Novaković VINČA Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, University of Belgrade
  • Goran A Bogdanović VINČA Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, University of Belgrade
  • Srećko R Trifunović Department of Chemistry, Faculty of Science, University of Kragujevac
  • Gordana P Radić Faculty of Medical Sciences, University of Kragujevac

DOI:

https://doi.org/10.20450/mjcce.2016.729

Keywords:

meso-1, 2-diphenyl-ethylenediamine-N, N'-di-3-propanoic acid, platinum(IV) complex, palladium(II) complex, crystal structure, cytotoxicity

Abstract

The syntheses of tetradentate ligand, meso-1,2-diphenyl-ethylenediamine-N,N'-di-3-propanoic acid (H2-1,2-dpheddp) and corresponding platinum(IV) and palladium(II) complexes are reported here. The spectroscopically predicted structure of the obtained palladium(II) complex was confirmed by X-ray analysis. Singe crystals suitable for X-ray measurements were obtained by slow crystallization from a DMSO-water mixture. Cytotoxic effects of platinum(IV), palladium(II) complexes and cisplatin on the 4T1 and B16F1 cell lines were determined using the MTT colorimetric technique. The complexes showed a dose dependence on cytotoxic effect toward both cell lines. Both complexes were less active than cisplatin, the exception was concentrations above 62.5 μM of platinum(IV) complex in the B16F1 cell line.

 

References

B. Rosenberg, L. VanCamp, J. E. Trosko, V. H. Mansour, Platinum compounds: a new class of potent antitumour agents, Nature, 222, 385–386 (1969).

B. Rosenberg, L. VanCamp, The successful re-gression of large solid sarcoma 180 tumors by platinum compounds, Cancer Res., 6, 1799–1802 (1970).

E. Wong, C. M. Giandomenico, Current status of platinum-based antitumor drugs, Chem Rev., 99, 2451–2466 (1999).

B. Lippert, Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug, VHCA/Wiley-VCH, Weinheim, 1999, pp. 497.

G. Natile, M. Coluccia, Current status of trans-platinum compounds in cancer therapy, Coord. Chem. Rev., 216, 383–410 (2001).

J. N. Jolley, A. I. Yanovsky, L. R. Kelland, K. B. Nolan, Synthesis and antitumour activity of platinum(II) and platinum(IV) complexes contain¬ing ethylenediamine-derived ligands having alcohol, carboxylic acid and acetate substituents. Crystal and molecular structure of [PtL4Cl2]•H2O where L4 is ethylenediamine-N,N'-diacetate, J. Inorg. Biochem., 83, 91–100 (2001).

T. J. Sabo, G. N. Kaluđerović, D. Poleti, Lj. Karanović, A. Boccarelli, F. Cannito, G. Natile, Cytotoxicity of some platinum(IV) complexes with ethylenediamine-N,N'-di-3-propionato ligand, J. Inorg. Biochem., 98, 1378–1384 (2004).

G. P. Radić, V. V. Glođović, Z. R. Ratković, S. B. Novaković, S. G. Granda, L. Roces, L. M. Taboada, I. D. Radojević, O. D. Stefanović, Lj. R. Čomić and S. R. Trifunović, Synthesis, charac¬terization and antimicrobial activity of novel platinum(IV) and palladium(II) complexes with meso-1,2-diphenyl-ethylenediamine-N,N′-di-3-pro¬panoic acid – Crystal structure of H2-1,2-dpheddp•2HCl•H2O, J. Mol. Struct., 1029, 180–186 (2012).

C. F. Liu, C. H. Liu, Some homo- and heteropolynuclear chelates, Inorg. Chem., 3, 678–680 (1964).

S. J. Tripett, Notes, Chem. Soc., 4407 (1957).

CrysAlisPro, Version 1.171.36.24. Oxford Diffraction Ltd. Abington, England, 2012.

G. M. Sheldrick, A short history of SHELX, Acta Crystallogr., A64, 112–122 (2008).

M. Nardelli, Parst: A system of fortran routines for calculating molecular structure parameters from results of crystal structure analyses, Comput. Chem., 7, 95–98 (1983).

L. J. Farrugia, ORTEP-3 for Windows – A version of ORTEP-III with a Graphical User Interface (GUI), J. Appl. Crystallogr., 30, 565 (1997).

H. D. Flack, On enantiomorph-polarity estimation, Acta Crystallogr., A39, 876–881 (1983).

T. Mosmann, Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays, J. Immunol Methods., 65(1–2), 55–63 (1983).

F. H. Allen, The Cambridge Structural Database: a quarter of a million crystal structures and rising, Acta Crystallogr., B58, 380–388 (2002).

G. N. Kaluđerović, G. A. Bogdanović, T. J. Sabo, Synthesis and crystal structure of trans-dichloro(ethylenediamine-N,N'-di-3-propionato) platinum(IV) monohydrate, J. Coord. Chem., 55, 817–822 (2002); T. J. Sabo, G. N. Kaluđerović, S. R. Grgurić-Šipka, F. W. Heinemann, S. R. Trifunović, Complex compounds of platinum(IV) and O,O-dialkyl-ethylenediamine-N,N'-di-3-propanoate lig¬ands. A structural evidence for geometry of hydrolytic product of some esters. Inorg. Chem. Commun., 7, 241–244 (2004).

T. J. Sabo, G. N. Kaluđerović, D. Poleti, LJ. Karanović, A. Boccarelli, F. Cannito, G. Natile, Cytotoxicity of some platinum(IV) complexes with ethylenediamine-N,N'-di-3-propionato ligand, J. Inorg. Biochem., 98, 1378–1384 (2004).

Z. D. Matović, G. Pelosi, S. Ianelli, G. Ponticelli, D. D. Radanović, D. J. Radanović, Square-pyramidal copper(II) complexes of linear tetra-dentate edda-type ligands forming six-membered rings. Molecular structures of [Cu(1,3-pdda)(H2O)] and [Cu(eddp)(H2O)]·3.5H2O, Inorg. Chim., Acta 268, 221–230 (1998).

S. Grubišić, M. Gruden-Pavlović, S. R. Niketić, N. Sakagami-Yoshida, S. Kaizaki, Structural charac¬terization of the trans-equatorial isomer of (aqua) (ethylenediamine-N,N,N'-tri-propionato)chromium (III)trihydrate, [Cr(edtrp)(H2O)]·3H2O, Trans. Met. Chem., 28, 37–42 (2003).

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Published

2016-04-18

How to Cite

Mijajlović, M. Ž, Nikolić, M. V., Jevtić, V. V., Ratković, Z. R., Milovanović, J., Arsenijević, A., Stojanović, B., Novaković, S. B., Bogdanović, G. A., Trifunović, S. R., & Radić, G. P. (2016). Cytotoxicity of platinum(IV) and palladium(II) complexes with meso-1,2-diphenyl-ethylenediamine-N,N’-di-3-propanoic acid. Crystal structure of [Pd(1,2-dpheddp)] complex. Macedonian Journal of Chemistry and Chemical Engineering, 35(1), 79–86. https://doi.org/10.20450/mjcce.2016.729

Issue

Vol. 35 No. 1 (2016)

Section

Inorganic Chemistry

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