Caged mitochondrial uncouplers that are released in response to hydrogen peroxide

TETRAHEDRON

卷:66

Article

Quin, Caroline¹  Robertson, Linsey¹  McQuaker, Stephen J.¹  Price, Nicholas C.³  Brand, Martin D.²  Hartley, Richard C.¹ 

[1] Univ Glasgow, WestCHEM Dept Chem, Ctr Chem Res Ageing, Glasgow G12 8QQ, Lanark, Scotland

[2] Buck Inst Age Res, Novato, CA 94945 USA

[3] Univ Glasgow, Fac Biomed & Life Sci, Glasgow G12 8QQ, Lanark, Scotland

关键词: Mitochondria;    Caged;    Uncoupler;    Boronate;    Hydrogen peroxide;    Ageing;    Oxidative stress;    ROS;   

DOI  :  10.1016/j.tet.2010.01.103

来源: Elsevier

【 摘 要 】

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. (C) 2010 Elsevier Ltd. All rights reserved.

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