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Tetrahedron. 2009 Sep 26;65(39):8154-8160.

Synthesis of a mitochondria-targeted spin trap using a novel Parham-type cyclization.

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Centre for the Chemical Research of Ageing, WestCHEM Department of Chemistry, University of Glasgow, Glasgow, G12 8QQ, UK.


A new cyclic nitrone spin trap, [4-(3',3'-dibutyl-2'-oxy-3'H-isoindol-5'-yloxy)butyl]triphenylphosphonium bromide (MitoSpin), bearing a lipophilic cation has been prepared by a route that involves a novel Parham-type lithiation-cyclization of an isocyanate to give the isoindolinone core. MitoSpin accumulates in a membrane potential dependent way in energized mitochondria and its oxidation could potentially be used in the study of oxidative stress resulting from reactive oxygen species generated in mitochondria.

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