Caged mitochondrial uncouplers that are released in response to hydrogen peroxide

Caroline Quin; Linsey Robertson; Stephen J McQuaker; Nicholas C Price; Martin D Brand; Richard C Hartley

doi:10.1016/j.tet.2010.01.103

Caged mitochondrial uncouplers that are released in response to hydrogen peroxide

Tetrahedron. 2010 Mar 27;66(13):2384-2389. doi: 10.1016/j.tet.2010.01.103.

Authors

Caroline Quin¹, Linsey Robertson, Stephen J McQuaker, Nicholas C Price, Martin D Brand, Richard C Hartley

Affiliation

¹ Centre for the Chemical Research of Ageing, WestCHEM Department of Chemistry, 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.