Caged mitochondrial uncouplers that are released in response to hydrogen peroxide

Quin, C., Robertson, L., McQuaker, S.J., Price, N.C., Brand, M.D. and Hartley, R.C. (2010) Caged mitochondrial uncouplers that are released in response to hydrogen peroxide. Tetrahedron, 66(13), pp. 2384-2389. (doi:10.1016/j.tet.2010.01.103) (PMID:20418941) (PMCID:PMC2852674)

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Abstract

Caged versions of the most common mitochondrial uncouplers (proton translocators) have been prepared that sense the reactive oxygen species (ROS) hydrogen peroxide to release the uncouplers 2,4-dinitrophenol (DNP) and carbonylcyanide p-trifluoromethoxyphenylhydrazone (FCCP) from caged states with second order rate constants of 10 (±0.8) M<sup>−1</sup> s<sup>−1</sup> and 64.8 (±0.6) M<sup>−1</sup> s<sup>−1</sup>, respectively. The trigger mechanism involves conversion of an arylboronate into a phenol followed by fragmentation. Hydrogen peroxide-activated uncouplers may be useful for studying the biological process of ageing.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Hartley, Professor Richard and Price, Prof Nicholas and Robertson, Dr Linsey
Authors: Quin, C., Robertson, L., McQuaker, S.J., Price, N.C., Brand, M.D., and Hartley, R.C.
Subjects:Q Science > QH Natural history > QH345 Biochemistry
College/School:College of Medical Veterinary and Life Sciences > School of Life Sciences
College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron
Publisher:Elsevier
ISSN:0040-4020
ISSN (Online):1464-5416
Published Online:02 February 2010
Copyright Holders:Copyright © 2010 Elsevier
First Published:First published in Tetrahedron 66(13):2384-2389
Publisher Policy:Reproduced in accordance with the copyright policy of the publisher

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