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

Content Provider	Springer Nature Link
Author	Sowden, Rebecca J. Trotter, Katherine D. Dunbar, Lynsey Craig, Gemma Erdemli, Omer Spickett, Corinne M. Reglinski, John
Copyright Year	2012
Abstract	A series of simple copper N2S2 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.
Starting Page	85
Ending Page	96
Page Count	12
File Format	PDF
ISSN	09660844
Journal	BioMetals
Volume Number	26
Issue Number	1
e-ISSN	15728773
Language	English
Publisher	Springer Netherlands
Publisher Date	2012-11-18
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Copper macrocycles Oxidation–reduction Glutathione Ascorbate Vitamin E Oxidative stress Biochemistry Pharmacology/Toxicology Microbiology Cell Biology Plant Physiology Medicine/Public Health
Content Type	Text
Resource Type	Article
Subject	Metals and Alloys Biochemistry, Genetics and Molecular Biology Biomaterials Agricultural and Biological Sciences

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