Second generation of alpha-tocopherol analogs-nitric oxide donors: Synthesis, physicochemical, and biological characterization

Bioorg Med Chem. 2007 Sep 15;15(18):6262-72. doi: 10.1016/j.bmc.2007.06.019. Epub 2007 Jun 13.

Abstract

Synthesis, physicochemical, and biological characterization of a series of alpha-tocopherol mimetics with NO-releasing capacity are reported. The selected NO-donor moieties were nitrooxy and furoxan. All products were tested for their in vitro NO-releasing capacities, vasodilating properties and mammal cytotoxic activities. The lipophilic-hydrophilic balance of all products was also evaluated. A new hybrid furoxan, phenol derivative 17, possesses adequate profile of the studied properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Aorta, Thoracic / drug effects
  • Cell Proliferation / drug effects
  • Macrophages / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide / metabolism*
  • Nitric Oxide Donors / chemical synthesis
  • Nitric Oxide Donors / chemistry
  • Nitric Oxide Donors / pharmacology*
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / chemistry
  • Oxadiazoles / pharmacology
  • Rats
  • Rats, Inbred WKY
  • Vasodilation / drug effects
  • Vasodilator Agents / chemical synthesis
  • Vasodilator Agents / chemistry
  • Vasodilator Agents / pharmacology*
  • X-Ray Diffraction
  • alpha-Tocopherol / chemical synthesis*
  • alpha-Tocopherol / chemistry
  • alpha-Tocopherol / pharmacology

Substances

  • Antioxidants
  • Nitric Oxide Donors
  • Oxadiazoles
  • Vasodilator Agents
  • furoxans
  • Nitric Oxide
  • alpha-Tocopherol