An alternative standard for Trolox-equivalent antioxidant-capacity estimation based on thiol antioxidants. Comparative 2,2'-azinobis[3-ethylbenzothiazoline-6-sulfonic acid] decolorization and rotational viscometry study regarding hyaluronan degradation

Chem Biodivers. 2010 Sep;7(9):2191-200. doi: 10.1002/cbdv.201000019.

Abstract

Comparison of the effectiveness of antioxidant activity of three thiol compounds, D-penicillamine, reduced L-glutathione, and 1,4-dithioerythritol, expressed as a radical-scavenging capacity based on the two independent methods, namely a decolorization 2,2'-azinobis[3-ethylbenzothiazoline-6-sulfonic acid] assay and a rotational viscometry, is reported. Particular concern was focused on the testing of potential free-radical scavenging effects of thiols against hyaluronan degradation, induced by hydroxyl radicals. A promising, solvent-independent, antioxidative function of 1,4-dithioerythritol, comparable to that of a standard compound, Trolox(®), was confirmed by the 2,2'-azinobis[3-ethylbenzothiazoline-6-sulfonic acid] assay. The new potential antioxidant 1,4-dithioerythritol exhibited very good solubility in a variety of solvents (e.g., H(2)O, EtOH, and DMSO) and could be widely accepted and used as an effective antioxidant standard instead of a routinely used Trolox(®) on 2,2'-azinobis[3-ethylbenzothiazoline-6-sulfonic acid] assay.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry*
  • Antioxidants / pharmacology
  • Benzothiazoles
  • Chromans / chemistry*
  • Chromans / pharmacology
  • Dithioerythritol / chemistry
  • Drug Evaluation, Preclinical / methods*
  • Free Radical Scavengers / chemistry
  • Glutathione / chemistry
  • Hyaluronic Acid / chemistry*
  • Hyaluronic Acid / pharmacology
  • Hydroxyl Radical / chemistry
  • Oxidation-Reduction
  • Penicillamine / chemistry
  • Solubility
  • Solvents
  • Spectrophotometry
  • Structure-Activity Relationship
  • Sulfhydryl Compounds / chemistry*
  • Sulfhydryl Compounds / pharmacology
  • Sulfonic Acids / chemistry*
  • Thiazoles / chemistry*
  • Viscosity

Substances

  • Antioxidants
  • Benzothiazoles
  • Chromans
  • Free Radical Scavengers
  • Solvents
  • Sulfhydryl Compounds
  • Sulfonic Acids
  • Thiazoles
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
  • Hydroxyl Radical
  • Dithioerythritol
  • Hyaluronic Acid
  • Glutathione
  • Penicillamine
  • 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid