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Copper(II) complexes based on tripodal pyrazolyl amines: Synthesis, structure, magnetic properties and anticancer activity

SS. Massoud, FR. Louka, GT. Ducharme, RC. Fischer, FA. Mautner, J. Vančo, R. Herchel, Z. Dvořák, Z. Trávníček,

. 2018 ; 180 (-) : 39-46. [pub] 20171205

Language English Country United States

Document type Journal Article, Research Support, Non-U.S. Gov't

Persistent link   https://www.medvik.cz/link/bmc19001043

The Cu(II) complexes [Cu(bpdmpz)Cl]ClO4 (1), [Cu(bdmpzp)Cl]ClO4 (2-ClO4), [Cu(bdmpzp)Cl]PF6 (2-PF6) and [Cu(tdmpza)Cl]ClO4 (3), bpdmpzp=[bis[((2-pyridylmethyl)-di(3,5-dimethyl-1H-pyrazolyl)methyl)]amine, bdmpzp=[bis((di(3,5-dimethyl-1H-pyrazolyl)methyl)-(2-pyridylmethyl)]amine and tdmpza=tris[di(3,5-dimethyl-1H-pyrazolyl)-methyl)]amine were synthesized and characterized by elemental analysis, magnetic and conductivity measurements, electrospray-ionization mass spectrometry, infrared and electronic spectroscopy, and X-ray crystallography. The magnetic properties of the complexes, measured at variable temperature, revealed weak antiferromagnetic intermolecular interactions. The cytotoxicity of the complexes 1, 2-ClO4, 3, and 4 ([Cu(bedmpzp)Cl]PF6, where bedmpzp=[bis(3,5-dimethyl-1H-pyrazol-1-yl-1-ethyl)-(2-pyridylmethyl)]amine), was investigated against four human cancer cell lines: A2780 (ovarian), A2780R (cisplatin-resistant variant), HOS (aggressive bone tumors), CaCo2 (epithelial colorectal adenocarcinoma) and on healthy human hepatocytes. The complex 4 was the most cytotoxic one, with IC50=1.4μM (A2780), 8.3μM (A2780R), 4.7μM (HOS) and 10.8μM (CaCo2). The mass spectrometry-based interaction studies, involving selected sulfur-containing biomolecules and small model proteins, revealed pro-oxidant effects of complexes 1 and 4 and differences in stability of both complexes in the mixtures containing the model protein cytochrome c after 24h incubation, complex 1 formed 1:1 adduct, the formation of which was accompanied by the loss of one dimethylpyrazole pendant arm from the bpdmpz ligand, while the complex 4 composition remained intact and the complex formed both 1:1 and 1:2 adducts (cytochrome c vs. Cu(II)-complex).

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$a Massoud, Salah S $u Department of Chemistry, University of Louisiana at Lafayette, Lafayette, LA 70504, USA. Electronic address: ssmassoud@louisiana.edu.
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$a Copper(II) complexes based on tripodal pyrazolyl amines: Synthesis, structure, magnetic properties and anticancer activity / $c SS. Massoud, FR. Louka, GT. Ducharme, RC. Fischer, FA. Mautner, J. Vančo, R. Herchel, Z. Dvořák, Z. Trávníček,
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$a The Cu(II) complexes [Cu(bpdmpz)Cl]ClO4 (1), [Cu(bdmpzp)Cl]ClO4 (2-ClO4), [Cu(bdmpzp)Cl]PF6 (2-PF6) and [Cu(tdmpza)Cl]ClO4 (3), bpdmpzp=[bis[((2-pyridylmethyl)-di(3,5-dimethyl-1H-pyrazolyl)methyl)]amine, bdmpzp=[bis((di(3,5-dimethyl-1H-pyrazolyl)methyl)-(2-pyridylmethyl)]amine and tdmpza=tris[di(3,5-dimethyl-1H-pyrazolyl)-methyl)]amine were synthesized and characterized by elemental analysis, magnetic and conductivity measurements, electrospray-ionization mass spectrometry, infrared and electronic spectroscopy, and X-ray crystallography. The magnetic properties of the complexes, measured at variable temperature, revealed weak antiferromagnetic intermolecular interactions. The cytotoxicity of the complexes 1, 2-ClO4, 3, and 4 ([Cu(bedmpzp)Cl]PF6, where bedmpzp=[bis(3,5-dimethyl-1H-pyrazol-1-yl-1-ethyl)-(2-pyridylmethyl)]amine), was investigated against four human cancer cell lines: A2780 (ovarian), A2780R (cisplatin-resistant variant), HOS (aggressive bone tumors), CaCo2 (epithelial colorectal adenocarcinoma) and on healthy human hepatocytes. The complex 4 was the most cytotoxic one, with IC50=1.4μM (A2780), 8.3μM (A2780R), 4.7μM (HOS) and 10.8μM (CaCo2). The mass spectrometry-based interaction studies, involving selected sulfur-containing biomolecules and small model proteins, revealed pro-oxidant effects of complexes 1 and 4 and differences in stability of both complexes in the mixtures containing the model protein cytochrome c after 24h incubation, complex 1 formed 1:1 adduct, the formation of which was accompanied by the loss of one dimethylpyrazole pendant arm from the bpdmpz ligand, while the complex 4 composition remained intact and the complex formed both 1:1 and 1:2 adducts (cytochrome c vs. Cu(II)-complex).
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$a Louka, Febee R $u Department of Chemistry, University of Louisiana at Lafayette, Lafayette, LA 70504, USA.
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$a Ducharme, Gerard T $u Department of Chemistry, University of Louisiana at Lafayette, Lafayette, LA 70504, USA.
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$a Fischer, Roland C $u Institut für Anorganische Chemische, Technische Universität Graz, Stremayrgasse 9/V, A-8010 Graz, Austria.
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$a Mautner, Franz A $u Institut für Physikalische and Theoretische Chemie, Technische Universität Graz, Stremayrgasse 9/II, A-8010 Graz, Austria. Electronic address: mautner@tugraz.at.
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$a Vančo, Ján $u Division of Biologically Active Complexes and Molecular Magnets, Regional Centre of Advanced Technologies and Materials, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic.
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$a Herchel, Radovan $u Division of Biologically Active Complexes and Molecular Magnets, Regional Centre of Advanced Technologies and Materials, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic.
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$a Dvořák, Zdeněk $u Division of Biologically Active Complexes and Molecular Magnets, Regional Centre of Advanced Technologies and Materials, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic.
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$a Trávníček, Zdeněk $u Division of Biologically Active Complexes and Molecular Magnets, Regional Centre of Advanced Technologies and Materials, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic. Electronic address: zdenek.travnicek@upol.cz.
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