Three, structurally characterised, bis-phen Cu(II) complexes of the phthalate isomers display rapid, low micromolar in vitro cytotoxicity against a range of epithelial tumour cells. The complexes induce relaxation of supercoiled plasmid DNA in the absence of external reducing agents and display efficient CT-DNA, Poly[d(A-T)](2) and Poly[d(G-C)](2) binding.
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http://dx.doi.org/10.1039/c0dt01607a | DOI Listing |
Angew Chem Int Ed Engl
January 2025
Institut de Chimie (UMR 7177), University of Strasbourg, CNRS, 4 Rue Blaise Pascal, 67081, Strasbourg, France.
Several copper-ligands, including 1,10-phenanthroline (Phen), have been investigated for anticancer purposes based on their capacity to bind excess copper (Cu) in cancer tissues and form redox active complexes able to catalyse the formation of reactive oxygen species (ROS), ultimately leading to oxidative stress and cell death. Glutathione (GSH) is a critical compound as it is highly concentrated intracellularly and can reduce and dissociate copper(II) from the ligand forming poorly redox-active copper(I)-thiolate clusters. Here we report that Cu-Phen speciation evolves in physiologically relevant GSH concentrations.
View Article and Find Full Text PDFMolecules
May 2023
Department of Chemistry, Maynooth University, W23 NPY6 Maynooth, Ireland.
The interest in the use of copper as a metal scaffold for the development of novel chemotherapeutics has considerably grown in recent years. This is mainly due to the relatively lower toxicity of copper complexes with respect to platinum drugs (i.e.
View Article and Find Full Text PDFNanoscale
June 2019
Department of Chemistry, McGill University, 801 Sherbrooke St. W., Montreal, Quebec, Canada.
Herein we present a new strategy to achieve chiral induction and redox switching along the backbone of metallohelicate architectures, wherein a DNA duplex directs the handedness and charge transport properties of a metal-organic assembly more than 60 bonds away (a distance of >10 nm). The quantitative and site-specific binding of copper(i) ions to DNA-templated coordination sites imparts enhanced thermodynamic stability to the assembly, while the DNA duplex transfers its natural right-handed helicity to the proximal and distal metal centers of the helicates. When copper(ii) ions are employed instead of copper(i) ions, spontaneous DNA-mediated reduction occurs, which we propose is followed by a slower change in coordination environment (from pentacoordinate CuII to tetrahedral CuI) to generate copper(i) helicates.
View Article and Find Full Text PDFChemSusChem
July 2016
Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8049, Zurich, Switzerland.
A new, general reaction scheme for photocatalytic hydrogen production is presented based on oxidative quenching of a homoleptic copper(I) bis-1,10-phenanthroline photosensitizer (PS) by 1-methyl-4-phenyl-pyridinium (MPP(+) ) as the electron relay and subsequent regeneration of the so formed copper(II) complex by a sacrificial electron donor. Electron transfer from the relay to various cobalt based water reduction catalysts and subsequent H2 production was shown to close the catalytic cycle. Transient absorption experiments unambiguously confirmed the proposed pathway, both the oxidative quenching and subsequent regeneration of oxidized PS.
View Article and Find Full Text PDFBioorg Med Chem
January 2016
Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, 28805 Alcalá de Henares (Madrid), Spain. Electronic address:
We report in this article the interactions of five N-(1,10-phenanthrolin-5-yl)-β-glycopyranosylamine copper(II) complexes with G-quadruplex DNA. Specifically, the interactions of these compounds with a human telomeric oligonucleotide have been assessed by fluorescence-based assays (FRET melting and G4-FID), circular dichroism and competitive equilibrium dialysis experiments. The metal complexes bind and stabilize G-quadruplex DNA structures with apparent association constants in the order of 10(4)-10(5)M(-1) and the affinity observed is dependent on the ionic conditions utilized and the specific nature of the carbohydrate moiety tethered to the 1,10-phenanthroline system.
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