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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

(A) Numbering scheme for assignment of NMR spectra of MitoEn. (B) Key H–H correlations:  gCOSY,  NOESY. (C) Key H–C correlations:  HMBC,  mutual HMBC.
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fig2: (A) Numbering scheme for assignment of NMR spectra of MitoEn. (B) Key H–H correlations: gCOSY, NOESY. (C) Key H–C correlations: HMBC, mutual HMBC.

Mentions: The NMR spectra for the mesylates MitoE2 (1), MitoE4 (2), MitoE6 (3), MitoE10 (4) and MitoE11 (5) displayed a number of common features which are summarized in Fig. 2 and Table 1. As an example the 1H NMR spectrum of MitoE6 (3) contained a triplet at δ 2.55 (J=6.8 Hz), consistent with the signal from the methylene group at position 4. NOESY and gCOSY correlations from this resonance to a multiplet at δ 1.66–1.80 allowed assignment to the methylene protons at 3. Both of these signals had NOESY correlations to a 3-proton singlet at δ 1.17 therefore assigned to the methyl protons at 12. The resonances from the aryl methyl groups were identified from NOESY correlations as from the protons at 10 (δ 2.10) and 11 (δ 2.00) and a correlation between the signal from the remaining methyl group 9 (δ 2.07) and the methylene resonance of 4. The signal from the protons at position 6′ was clearly evident as a multiplet at δ 3.22–3.30.


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

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

(A) Numbering scheme for assignment of NMR spectra of MitoEn. (B) Key H–H correlations:  gCOSY,  NOESY. (C) Key H–C correlations:  HMBC,  mutual HMBC.
© Copyright Policy - CC BY
Related In: Results  -  Collection

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

fig2: (A) Numbering scheme for assignment of NMR spectra of MitoEn. (B) Key H–H correlations: gCOSY, NOESY. (C) Key H–C correlations: HMBC, mutual HMBC.
Mentions: The NMR spectra for the mesylates MitoE2 (1), MitoE4 (2), MitoE6 (3), MitoE10 (4) and MitoE11 (5) displayed a number of common features which are summarized in Fig. 2 and Table 1. As an example the 1H NMR spectrum of MitoE6 (3) contained a triplet at δ 2.55 (J=6.8 Hz), consistent with the signal from the methylene group at position 4. NOESY and gCOSY correlations from this resonance to a multiplet at δ 1.66–1.80 allowed assignment to the methylene protons at 3. Both of these signals had NOESY correlations to a 3-proton singlet at δ 1.17 therefore assigned to the methyl protons at 12. The resonances from the aryl methyl groups were identified from NOESY correlations as from the protons at 10 (δ 2.10) and 11 (δ 2.00) and a correlation between the signal from the remaining methyl group 9 (δ 2.07) and the methylene resonance of 4. The signal from the protons at position 6′ was clearly evident as a multiplet at δ 3.22–3.30.

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