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)

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⁻¹ s⁻¹ and 64.8 (±0.6) M⁻¹ s⁻¹, 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