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Four 2-oxo-1,2-dihydroquinoline-3-carbaldehyde N-substituted thiosemicarbazone ligands (H(2)-OQtsc-R, where R = H, Me, Et or Ph) and their corresponding new copper(II) complexes [CuCl(2)(H(2)-OQtsc-H)]·2H(2)O (1), [CuCl(2)(H(2)-OQtsc-Me)]·2H(2)O (2), [CuCl(2)(H(2)-OQtsc-Et)(CH(3)OH)]Cl (3) and [CuCl(H-OQtsc-Ph)]·CH(3)OH (4) have been synthesized in order to correlate the effect of terminal N-substitution on coordination behaviour, structure and biological activity. Single crystal X-ray diffraction studies revealed that the complexes 1, 2 and 3 have square pyramidal geometry around the central metal ion. In the complexes 1 and 2, the copper ion is coordinated by the ligand with ONS donor atoms, one chloride ion in apical position and the other chloride in the basal plane. Complex 3 consists of [CuCl(2)(H(2)-OQtsc-Et)(CH(3)OH)](+) cation and a chloride as counter ion. The copper ion is coordinated by the ligand with ONS donor atoms and by one chloride ion in the basal plane. One methanol molecule is bonded through its neutral oxygen in the apical position. Complex 4 is square planar with the ligand coordinating through uni-negative tridentate ONS(-) and by one chloride ion in the basal plane. The binding of complexes with lysozyme protein was carried out by fluorescence spectroscopy. Investigations of antioxidation properties showed that all the copper(II) complexes have strong radical scavenging properties. The cytotoxicity of the complexes 3 and 4 against NIH 3T3 and HeLa cell lines showed that synergy between the metal and ligands results in a significant enhancement in the cell death with IC(50) of ~10-40 μM. A size dependence of substitution at terminal N in the thiosemicarbazones on the biological activities of the complexes has been observed.
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http://dx.doi.org/10.1039/c0dt01657h | DOI Listing |
ChemMedChem
December 2024
University of Puerto Rico Rio Piedras: Universidad de Puerto Rico Recinto de Rio Piedras, Chemistry, 17 University Avenue, 00925, San Juan, UNITED STATES OF AMERICA.
Deferasirox (Def), an orally administered iron-chelating drug, has drawn significant interest in repurposing for anticancer application due to the elevated Fe demand by cancer cells. But there are also concerns about its severe off target health effects. Herein Cu(II) binding is studied as a potential off target interaction.
View Article and Find Full Text PDFMolecules
November 2024
Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102A, HR-10000 Zagreb, Croatia.
In this study, we report the syntheses, crystal structures and magnetic properties of ternary copper(II) coordination compounds with l-homoserine (l-Hhser) and 1,10-phenanthroline (phen). Six new coordination compounds were obtained: [Cu(l-hser)(HO)(phen)]SO·5HO (), [Cu(μ-l-hser)(HO)(phen)][Cu(l-hser)(HO)(phen)](SO)∙12HO (), {[Cu(μ-l-hser)(HO)(phen)][Cu(μ-l-hser)(phen)]SO·6HO} (), {[Cu(μ-l-hser)(HO)(phen)]SO·3HO} (), [Cu(l-hser)(HO)(phen)][Cu(l-hser)(CHOH)(phen)]SO·4HO () and {[Cu(l-hser)(CHOH)(phen)][Cu(μ-l-hser)(phen)]SO·5CHOH} () It was shown that slight differences in water content in the synthetic mixtures highly influence the final product, so in some cases, two or three different products were obtained. The compounds were characterized by single-crystal X-ray diffraction and ESR spectroscopy.
View Article and Find Full Text PDFNanophotonics
June 2024
Materials Structural Dynamics Laboratory, Department of Chemistry, Wayne State University, 48202, Detroit, MI, USA.
It remains unclear how the collective strong coupling of cavity-confined photons to the electronic transitions of molecular chromophore leverages the distinct properties of the polaritonic constituents for future technologies. In this study, we design, fabricate, and characterize multiple types of Fabry-Pérot (FP) mirco-resonators containing copper(II) tetraphenyl porphyrin (CuTPP) to show how cavity polariton formation affects radiative relaxation processes in the presence of substantial non-Condon vibronic coupling between two of this molecule's excited electronic states. Unlike the prototypical enhancement of Q state radiative relaxation of CuTPP in a FP resonator incapable of forming polaritons, we find the light emission processes in multimode cavity polariton samples become enhanced for cavity-exciton energy differences near those of vibrations known to mediate non-Condon vibronic coupling.
View Article and Find Full Text PDFChemistry
December 2024
School of Chemistry, University of Leeds, Woodhouse Lane, Leeds, LS2 9JT, UK.
Cage-catenanes are chemical constructs where two or more cage-like molecules or assemblies are mechanically interlocked together. We report a new class of cage-catenanes where dimeric metal-organic cage-catenanes are linked into larger assemblies through additional bridging metal chloride links. These crystalline materials are obtained from the reaction of tris(nicotinoyl)cyclotriguaiacylene (L1) with Cu(II) salts, and all feature a tetramer of cages where two {Cu(L1)(X)} cages (X=anion) are mechanically interlocked, and link to each other and to another {Cu(L1)(X)} cage-catenane through a planar, linear tetranuclear {Cu(μ-Cl)Cl} cluster.
View Article and Find Full Text PDFDalton Trans
December 2024
Anorganisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
, an obligate symbiont of certain ascidians (sea squirts found in tropical areas), produces various cyclic pseudo-octapeptides in large quantities. These secondary metabolites have attracted the attention of medicinal chemists and, due to their four azol(in)e and four amide donor groups, coordination chemists have become interested in these molecules. The structures of the metal-free macrocycles and their dinuclear copper(II) complexes are known, and solution equilibria, spectroscopic properties and a range of biologically relevant reactions have been studied in detail.
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