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Issue 6, 2017
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Copper(ii) complexes with benzhydrazone-related ligands: synthesis, structural studies and cytotoxicity assay

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Abstract

The dinuclear copper(II) complexes [Cu2(LH)2] (1), [Cu2(L3OMe)2] (2), [Cu2(L4OMe)2] (3) as well as the tetranuclear complex [Cu4(L3OMe)4]·4MeOH·2H2O (2a·4MeOH·2H2O), (where LH = 2-oxybenzaldehyde benzhydrazonato, L3OMe = 3-methoxy-2-oxybenzaldehyde benzhydrazonato or L4OMe = 4-methoxy-2-oxybenzaldehyde benzhydrazonato) were synthesized by reacting copper(II) acetate with the corresponding aroylhydrazone. Reactions in the presence of N-donor ligands D (pyridine, 4,4′-bipyridine or 1,10-phenanthroline) afforded complexes with different nuclearities and Cu : L : D ratios. They can be classified as dinuclear, [Cu2(LH)2(py)2] (1py), [Cu2(L3OMe)2(py)2]·3H2O (2py·3H2O), [Cu2(L4OMe)2(py)2] (3py), [{Cu(LH)}2(bpy)] (1bpy), [{Cu(L3OMe)}2(bpy)] (2bpy), and [{Cu(L4OMe)}2(bpy)] (3bpy), mononuclear [Cu(LH)(phen)] (1phen), [Cu(L3OMe)(phen)] (2phen) and [Cu(L4OMe)(phen)] (3phen), and polynuclear [{Cu(LH)}2(bpy)]n·2nMeOH (1bpy*·2MeOH) complexes. Conversion of complexes 1py–3py to complexes 1–3 proceeded via solid state reactions. The crystal and molecular structures of 2a·4MeOH·2H2O, 2py·3H2O, 3py, 1bpy*·2MeOH, 2bpy, 1phen and 3phen were determined by the single crystal X-ray diffraction method. All complexes were characterized by means of elemental and thermogravimetric analysis, FT-IR spectroscopy and the powder X-ray diffraction method. In vitro cytotoxicity of benzhydrazone-related ligands and their copper(II) complexes against THP-1 and HepG2 cells demonstrated that the complexes are significantly more cytotoxic than the corresponding ligands.

Graphical abstract: Copper(ii) complexes with benzhydrazone-related ligands: synthesis, structural studies and cytotoxicity assay

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Supplementary files

Article information


Submitted
07 Dec 2016
Accepted
09 Feb 2017
First published
10 Feb 2017

New J. Chem., 2017,41, 2425-2435
Article type
Paper

Copper(II) complexes with benzhydrazone-related ligands: synthesis, structural studies and cytotoxicity assay

M. Cindrić, A. Bjelopetrović, G. Pavlović, V. Damjanović, J. Lovrić, D. Matković-Čalogović and V. Vrdoljak, New J. Chem., 2017, 41, 2425
DOI: 10.1039/C6NJ03827A

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