Synthesis of triphenylphosphonium vitamin E derivatives as mitochondria-targeted antioxidants

A series of mitochondria-targeted antioxidants comprising a lipophilic triphenylphosphonium cation attached to the antioxidant chroman moiety of vitamin E by an alkyl linker have been prepared. The synthesis of a series of mitochondria-targeted vitamin E derivatives with a range of alkyl linkers gav...

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Bibliographic Details
Published inTetrahedron Vol. 71; no. 44; pp. 8444 - 8453
Main Authors Jameson, Victoria J.A., Cochemé, Helena M., Logan, Angela, Hanton, Lyall R., Smith, Robin A.J., Murphy, Michael P.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 04.11.2015
Elsevier
Pergamon Press
Subjects
Chemistry
Chemistry, Organic
Lipid peroxidation
Mitochondria
Mitochondria-targeted antioxidant
MitoE
Physical Sciences
Science & Technology
Vitamin E
MitoE
Lipid peroxidation
Mitochondria
Mitochondria-targeted antioxidant
Vitamin E
SYSTEM
CELLS
OXIDATIVE STRESS
MITOQ
UBIQUINONE
ALKYNE
DAMAGE
HEART
DISEASES
DYSFUNCTION
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Summary:A series of mitochondria-targeted antioxidants comprising a lipophilic triphenylphosphonium cation attached to the antioxidant chroman moiety of vitamin E by an alkyl linker have been prepared. The synthesis of a series of mitochondria-targeted vitamin E derivatives with a range of alkyl linkers gave compounds of different hydrophobicities. This work will enable the dependence of antioxidant defence on hydrophobicity to be determined in vivo. [Display omitted]
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ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.09.014