Novel antioxidant agents deriving from molecular combination of Vitamin C and NO-donor moieties

Bioorg Med Chem. 2008 May 1;16(9):5199-206. doi: 10.1016/j.bmc.2008.03.014. Epub 2008 Mar 6.

Abstract

In this paper, we describe a new class of products in which NO-donor moieties are linked to either the 3-OH (4a-f) or 2-OH group (7a-c) of ascorbic acid (ASA). Log Ps and pK(a)s of these products were experimentally evaluated. All the compounds were tested for their antioxidant activity on lipidic peroxidation induced by Fe(3+)-ADP/NADPH in lipids of microsomal membranes of rat hepatocytes. Only 3-O series displays antioxidant activity and it seems to be principally dependent on the lipophilicity. Both series trigger in vitro NO-dependent vasodilator properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry*
  • Antioxidants / classification
  • Aorta, Thoracic / drug effects
  • Ascorbic Acid / chemical synthesis*
  • Ascorbic Acid / chemistry
  • Ascorbic Acid / classification
  • Dose-Response Relationship, Drug
  • Lipid Peroxidation / drug effects
  • Lipids / chemistry
  • Magnetic Resonance Spectroscopy
  • Male
  • Microsomes / drug effects
  • Molecular Structure
  • Nitric Oxide Donors / chemical synthesis*
  • Nitric Oxide Donors / chemistry
  • Nitric Oxide Donors / classification
  • Rats
  • Rats, Wistar
  • Stereoisomerism
  • Structure-Activity Relationship
  • Time Factors

Substances

  • Antioxidants
  • Lipids
  • Nitric Oxide Donors
  • Ascorbic Acid