1. Caged mitochondrial uncouplers that are released in response to hydrogen peroxide
- Author
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Richard C. Hartley, Stephen J. McQuaker, Nicholas C. Price, Martin D. Brand, Caroline Quin, and Linsey Robertson
- Subjects
Reaction mechanism ,Hydrogen ,chemistry.chemical_element ,Mitochondrion ,010402 general chemistry ,Photochemistry ,01 natural sciences ,Biochemistry ,Article ,03 medical and health sciences ,chemistry.chemical_compound ,Reaction rate constant ,Caged ,Drug Discovery ,Organic chemistry ,Phenols ,Fragmentation (cell biology) ,Hydrogen peroxide ,030304 developmental biology ,chemistry.chemical_classification ,0303 health sciences ,Reactive oxygen species ,Organic Chemistry ,ROS ,0104 chemical sciences ,Mitochondria ,Ageing ,chemistry ,Oxidative stress ,Uncoupler ,Boronate - 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., Graphical abstract
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