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Synthesis, characterization, and cytotoxicity studies of Cu(II), Zn(II), and Fe(III) complexes ofN-derivatized 3-hydroxy-4-pyridiones

Authors
Journal
Journal of Inorganic Biochemistry
0162-0134
Publisher
Elsevier
Volume
132
Identifiers
DOI: 10.1016/j.jinorgbio.2013.12.003
Keywords
  • Hydroxypyridinone
  • Copper
  • Zinc
  • Iron
  • Metal Complex Cytotoxicity
  • Alzheimer'S Disease
Disciplines
  • Medicine
  • Physics

Abstract

Abstract The deleterious role of metal ions in Alzheimer's disease has inspired the study of various metal chelators. We previously showed the synthesis and in vitro activity of several bidentate hydroxypyridinone compounds, including 3-hydroxy-2-methyl-1-phenyl-4(1H)-pyridinone (1), 1-(4-aminophenyl)-3-hydroxy-2-methyl-4(1H)-pyridinone (2), and 1-(2-benzothiazolyl)-3-hydroxy-2-methyl-4(1H)-pyridinone (3). While the focus has been on the Cu(II) ion, the other biorelevant metals, Zn(II) and Fe(III) have been largely neglected. Herein, we report the synthesis of Zn(II) and Fe(III) complexes of ligands 1, 2, and 3, and their characterization by infrared (IR) spectroscopy, high resolution mass spectrometry (HR-MS), elemental analysis, and NMR, where applicable. Solid state structures of Zn(1)2, Fe(1)3, and Cu(3)2 are analyzed with X-ray crystallography. The cytotoxicity of pro-ligands 1, 2, and 3, and the three metal complexes of 2 are examined in a neuronal cell line to determine the effect of metal chelation on toxicity of the compounds.

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