Reactions of copper macrocycles with antioxidants and HOCl: potential for biological redox sensing

A series of simple copper N 2 S 2 macrocycles were examined for their potential as biological redox sensors, following previous characterization of their redox potentials and crystal structures. The divalent species were reduced by glutathione or ascorbate at a biologically relevant pH in aqueous bu...

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Veröffentlicht in:Biometals 2013-02, Vol.26 (1), p.85-96
Hauptverfasser: Sowden, Rebecca J., Trotter, Katherine D., Dunbar, Lynsey, Craig, Gemma, Erdemli, Omer, Spickett, Corinne M., Reglinski, John
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container_issue 1
container_start_page 85
container_title Biometals
container_volume 26
creator Sowden, Rebecca J.
Trotter, Katherine D.
Dunbar, Lynsey
Craig, Gemma
Erdemli, Omer
Spickett, Corinne M.
Reglinski, John
description A series of simple copper N 2 S 2 macrocycles were examined for their potential as biological redox sensors, following previous characterization of their redox potentials and crystal structures. The divalent species were reduced by glutathione or ascorbate at a biologically relevant pH in aqueous buffer. A less efficient reduction was also achieved by vitamin E in DMSO. Oxidation of the corresponding univalent copper species by sodium hypochlorite resulted in only partial (~65 %) recovery of the divalent form. This was concluded to be due to competition between metal oxidation and ligand oxidation, which is believed to contribute to macrocycle demetallation. Electrospray mass spectrometry confirmed that ligand oxidation had occurred. Moreover, the macrocyclic complexes could be demetallated by incubation with EDTA and bovine serum albumin, demonstrating that they would be inappropriate for use in biological systems. The susceptibility to oxidation and demetallation was hypothesized to be due to oxidation of the secondary amines. Consequently these were modified to incorporate additional oxygen donor atoms. This modification led to greater resistance to demetallation and ligand oxidation, providing a better platform for further development of copper macrocycles as redox sensors for use in biological systems.
doi_str_mv 10.1007/s10534-012-9596-9
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subjects Amines
Animals
Antioxidants
Antioxidants - chemistry
Ascorbic Acid - chemistry
Biochemistry
Biological
Biomedical and Life Sciences
Cattle
Cell Biology
Chelating Agents - chemistry
Coordination Complexes - chemistry
Copper
Copper - chemistry
Edetic Acid - chemistry
EDTA
Electrode potentials
Ethers, Cyclic - chemistry
Glutathione - chemistry
Hypochlorous Acid - chemistry
Life Sciences
Ligands
Macrocyclic compounds
Mass spectrometry
Medicine/Public Health
Microbiology
Molecular Weight
Oxidants - chemistry
Oxidation
Oxidation-Reduction
Oxidative stress
Pharmacology/Toxicology
Plant Physiology
Reducing Agents - chemistry
Reduction
Sensors
Serum Albumin, Bovine - chemistry
Sodium Hypochlorite - chemistry
Solutions
Sulfides - chemistry
Vitamin E
Vitamin E - chemistry
title Reactions of copper macrocycles with antioxidants and HOCl: potential for biological redox sensing
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