Tetrahedron

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

C Quin, J Trnka, A Hay, MP Murphy, RC Hartley

Index: Quin, Caroline; Trnka, Jan; Hay, Alison; Murphy, Michael P.; Hartley, Richard C. Tetrahedron, 2009 , vol. 65, # 39 p. 8154 - 8160

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Citation Number: 20

Abstract

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 ...