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Caged mitochondrial uncouplers that are released in response to hydrogen peroxide |
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| Authors: | Caroline Quin Stephen J McQuaker Martin D Brand |
| Institution: | a Buck Institute for Age Research, 8001 Redwood Boulevard, Novato, CA 94945, USA b Centre for the Chemical Research of Ageing, WestCHEM Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, United Kingdom c Faculty of Biomedical and Life Sciences, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, United Kingdom |
| 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. |
| Keywords: | Mitochondria Caged Uncoupler Boronate Hydrogen peroxide Ageing Oxidative stress ROS |
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