Synthesis of N-arylpyridinium salts bearing a nitrone spin trap as potential mitochondria-targeted antioxidants

Robertson, L. and Hartley, R. C. (2009) Synthesis of N-arylpyridinium salts bearing a nitrone spin trap as potential mitochondria-targeted antioxidants. Tetrahedron, 65(27), pp. 5284-5292. (doi:10.1016/j.tet.2009.04.083) (PMID:19693262) (PMCID:PMC2722452)

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Abstract

The generation of excess reactive oxygen species (ROS) in mitochondria is responsible for much of the oxidative stress associated with ageing (aging), and mitochondrial dysfunction is part of the pathology of neurodegeneration and type 2 diabetes. Lipophilic pyridinium ions are known to accumulate in mitochondria and this paper describes a general route for the preparation of nitrone-containing N-arylpyridinium salts having a range of lipophilicities, as potential therapeutic antioxidants. The compatibility of nitrones with the Zincke reaction is the key to their synthesis. Their trapping of carbon-centred radicals and the EPR spectra of the resulting nitroxides are reported.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Hartley, Professor Richard and Robertson, Dr Linsey
Authors: Robertson, L., and Hartley, R. C.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron
Publisher:Elsevier
ISSN:0040-4020
ISSN (Online):1464-5416
Published Online:04 May 2009
Copyright Holders:Copyright © 2009 Elsevier
First Published:First published in Tetrahedron 65(27):5284-5292
Publisher Policy:Reproduced in accordance with the copyright policy of the publisher

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