Journal of the Serbian Chemical Society 2023 Volume 88, Issue 12, Pages: 1279-1291
https://doi.org/10.2298/JSC230818072R
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Square-pyramidal mononuclear, dinuclear and polymeric copper(II) complexes with (2-pyridinylmethyl)amino derivatives
Richter Stefan (Universität Leipzig, Faculty of Chemistry and Mineralogy, Institute of Inorganic Chemistry, Leipzig, Germany)
Lönnecke Peter 
(Universität Leipzig, Faculty of Chemistry and Mineralogy, Institute of Inorganic Chemistry, Leipzig, Germany)
Bovan Dijana (Department of Immunology, Institute for Biological Research ”Siniša Stanković” National Institute of Republic of Serbia, University of Belgrade, Belgrade, Serbia)
Mijatović Sanja (Department of Immunology, Institute for Biological Research ”Siniša Stanković” National Institute of Republic of Serbia, University of Belgrade, Belgrade, Serbia)
Maksimović-Ivanić Danijela (Department of Immunology, Institute for Biological Research ”Siniša Stanković” National Institute of Republic of Serbia, University of Belgrade, Belgrade, Serbia)
Kaluđerović Goran N. (Department of Engineering and Natural Sciences, University of Applied Sciences Merseburg, Merseburg, Germany)
Hey-Hawkins Evamarie (Universität Leipzig, Faculty of Chemistry and Mineralogy, Institute of Inorganic Chemistry, Leipzig, Germany), hey@uni-leipzig.de
The coordination behavior of three ligand precursors 2-[(2-pyridinylmethyl) amino]acetic acid hydrochloride, 4-[(2-pyridinylmethyl)amino]benzoic acid hydrochloride and 4-{[2-(pyridin-2-ylmethylamino)ethylamino]methyl}- benzoic acid hydrochloride, HL1∙HCl–HL3∙HCl, respectively, in copper(II) complexes is described. The complexes were characterized by elemental analysis, ESI mass spectrometry and IR spectroscopy, as well as X-ray structural analysis. The reaction of copper(II) with HL1∙HCl in methanol afforded the polymeric complex [{Cu(μ-Cl)2(MeL1-κ2N,N’)}n] (1) featuring the methyl ester of L1 (MeL1). With HL2∙HCl or HL3∙HCl, the dimeric complex [{CuCl(μ-Cl)(HL2-κ2N,N’)}2] (2) or the mononuclear complex [CuCl2(HL3- κ3N,N’,N’’)] (3) were obtained. All complexes exhibited square-pyramidal geometries. In 1, polymeric chains are formed through bridging chlorido ligands without typical hydrogen bonding interaction. Contrarily, the COOH group in 2 is participating in the formation of intermolecular hydrogen bonding forming a supramolecular structure. In 3, intermolecular hydrogen bonding (Cl···H(O)) leads to a 1-D polymeric structure. The copper(II) complex 2 diminished viability of human 8505C, MCF-7, 518A2 and SW-480 cell lines. The tumoricidal effect of 2 was realized mainly through caspase-mediated apoptosis.
Keywords: copper(II), pyridine, X-ray structure, in vitro anticancer activity
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