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Synthesis of triphenylphosphonium vitamin E derivatives as mitochondria-targeted antioxidants.

Jameson VJ, Cochemé HM, Logan A, Hanton LR, Smith RA, Murphy MP - Tetrahedron (2015)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Otago, PO Box 56, Dunedin, 9054, New Zealand.

ABSTRACT

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.

No MeSH data available.


Related in: MedlinePlus

Prevention of oxidative damage to mitochondrial DNA in cells in culture by MitoE10. The lower the relative amplification the greater the damage to DNA.
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fig7: Prevention of oxidative damage to mitochondrial DNA in cells in culture by MitoE10. The lower the relative amplification the greater the damage to DNA.

Mentions: This showed that both MitoE2 and MitoE10 were comparably protective against mitochondrial lipid peroxidation and that both were more protective against oxidative damage that Trolox. Finally, the ability of the most effective version of MitoE, MitoE10 to protect against oxidative damage to mitochondrial DNA caused by the redox cycling molecule menadione was determined (Fig. 7). This also showed that MitoE10 was able to protect against this form of mitochondrial oxidative damage more effectively that the control compound decylTPP. MitoE2 was not protective in this assay (data not shown) consistent with the greater protection of MitoE10 against lipid peroxidation.


Synthesis of triphenylphosphonium vitamin E derivatives as mitochondria-targeted antioxidants.

Jameson VJ, Cochemé HM, Logan A, Hanton LR, Smith RA, Murphy MP - Tetrahedron (2015)

Prevention of oxidative damage to mitochondrial DNA in cells in culture by MitoE10. The lower the relative amplification the greater the damage to DNA.
© Copyright Policy - CC BY
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4596152&req=5

fig7: Prevention of oxidative damage to mitochondrial DNA in cells in culture by MitoE10. The lower the relative amplification the greater the damage to DNA.
Mentions: This showed that both MitoE2 and MitoE10 were comparably protective against mitochondrial lipid peroxidation and that both were more protective against oxidative damage that Trolox. Finally, the ability of the most effective version of MitoE, MitoE10 to protect against oxidative damage to mitochondrial DNA caused by the redox cycling molecule menadione was determined (Fig. 7). This also showed that MitoE10 was able to protect against this form of mitochondrial oxidative damage more effectively that the control compound decylTPP. MitoE2 was not protective in this assay (data not shown) consistent with the greater protection of MitoE10 against lipid peroxidation.

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Otago, PO Box 56, Dunedin, 9054, New Zealand.

ABSTRACT

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.

No MeSH data available.


Related in: MedlinePlus