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 Scopus citations

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

Keywords

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

ASJC Scopus subject areas

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

Cite this