Design, synthesis, and antioxidant activity of FeAOX-6, a novel agent deriving from a molecular combination of the chromanyl and polyisoprenyl moieties

Free Radic Biol Med. 2002 Dec 15;33(12):1724-35. doi: 10.1016/s0891-5849(02)01168-1.

Abstract

Several lines of evidence suggest potential benefits by a combination of carotenoids and tocopherols in chronic diseases. Therefore, we have designed FeAOX-6, a novel antioxidant that combines into a single molecule the chroman head of tocopherols and a fragment of lycopene, consisting of a polyisoprenyl sequence of four conjugated double bonds. The ability of FeAOX-6 in inhibiting lipid peroxidation and reactive oxygen species (ROS) production induced by different sources of free radicals (t-BOOH, AAPH, and H2O2) in arachidonic acid solution and in isolated thymocytes was investigated. Its antioxidant efficiency was also compared with that of alpha-tocopherol, lycopene, and a mixture of the two antioxidants. The results strongly suggest that FeAOX-6 can act as a potent antioxidant in our models, by inhibiting malondialdehyde production and ROS generation in a dose- and a time-dependent manner. In the cell model, the compound also provides a higher antioxidant capacity than alpha-tocopherol and lycopene, alone or in combination, suggesting the possibility of an oxidative intramolecular cooperation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Arachidonic Acid
  • Carotenoids / pharmacology
  • Cells, Cultured
  • Chromans / chemical synthesis*
  • Chromans / chemistry*
  • Chromans / pharmacology*
  • Drug Design*
  • Lipid Peroxidation / drug effects
  • Lycopene
  • Malondialdehyde / metabolism
  • Mice
  • Reactive Oxygen Species / metabolism
  • Solutions
  • Thymus Gland / cytology
  • Thymus Gland / drug effects
  • Thymus Gland / metabolism
  • Time Factors
  • Tocopherols / pharmacology

Substances

  • Antioxidants
  • Chromans
  • FeAOX-6
  • Reactive Oxygen Species
  • Solutions
  • Arachidonic Acid
  • Carotenoids
  • Malondialdehyde
  • Tocopherols
  • Lycopene