Design, synthesis, and evaluation of an α-tocopherol analogue as a mitochondrial antioxidant

Jun Lu, Omar Khdour, Jeffrey S. Armstrong, Sidney Hecht

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

An efficient synthesis has provided access to a novel α-tocopherol analogue (2), as well as its trifluoroacetate salt and acetate ester. An annulation reaction was used to establish the pyridinol core structure and a Stille coupling reaction was employed for conjugation with the tocopherol side chain. This analogue was shown to suppress the levels of reactive oxygen species in cultured cells, and to quench peroxidation of mitochondrial membranes.

Original languageEnglish (US)
Pages (from-to)7628-7638
Number of pages11
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number21
DOIs
StatePublished - Nov 1 2010

Fingerprint

Tocopherols
Antioxidants
Trifluoroacetic Acid
Mitochondrial Membranes
Cultured Cells
Reactive Oxygen Species
Esters
Acetates
Salts
Cells
Membranes

Keywords

  • α-Tocopherol analogue
  • Lipid peroxidation
  • Mitochondrial antioxidant
  • Mitochondrial dysfunction
  • Reactive oxygen species

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

Design, synthesis, and evaluation of an α-tocopherol analogue as a mitochondrial antioxidant. / Lu, Jun; Khdour, Omar; Armstrong, Jeffrey S.; Hecht, Sidney.

In: Bioorganic and Medicinal Chemistry, Vol. 18, No. 21, 01.11.2010, p. 7628-7638.

Research output: Contribution to journalArticle

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