The antioxidant screening of potential materials for drugs based on 6-nitro-1,2,4-triazoloazines containing natural polyphenol fragments

Anal Bioanal Chem. 2020 Aug;412(21):5147-5155. doi: 10.1007/s00216-020-02466-2. Epub 2020 Feb 20.

Abstract

The course of viral diseases is accompanied by excessive generation of active oxygen metabolites, so the effectiveness of treatment can be improved by combining antiviral and antioxidant therapy. There was a screening of antioxidant properties of 6-nitro-1,2,4-triazoloazine-modified fragments of natural polyphenols (catechol, pyrogallol, phloroglucinol, resorcinol) which are potential dual-action combination preparations. Screening was carried out using various approaches: the study of redox transformations by cyclic voltammetry, determination of antioxidant capacity with oxidizing agents of a radical and non-radical nature by the potentiometric method using potassium hexacyanoferrate (III) and optical methods (the Folin assay and the DPPH assay). It has been established that molecules obtained by conjugation of polyphenols with heterocycles exhibit antioxidant properties. The exception is adducts of triazolodiazines with resorcinol. A decrease in the antioxidant ability of synthesized adducts relative to initial polyphenols has been noted. The antioxidant capacity has been studied at a number of temperatures (25 °C, 37 °C), and the reaction half-life has been determined. The correlation of antioxidant capacity by a potentiometric assay with the Folin assay was R = 0.71; by a potentiometric assay with the DPPH assay was R = 0.67. Leader compounds have been identified. Graphical abstract.

Keywords: Antioxidant screening; DPPH assay; Folin assay; Polyphenols; Potentiometry; Triazoloazines.

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Half-Life
  • Molybdenum / chemistry
  • Oxidation-Reduction
  • Polyphenols / analysis*
  • Potentiometry / methods*
  • Triazoles / chemistry*
  • Tungsten Compounds / chemistry

Substances

  • Antioxidants
  • Antiviral Agents
  • Folin's phenol reagent
  • Polyphenols
  • Triazoles
  • Tungsten Compounds
  • Molybdenum