New triazole-bearing gramine derivatives - synthesis, structural analysis and protective effect against oxidative haemolysis

Nat Prod Res. 2022 Jul;36(13):3413-3419. doi: 10.1080/14786419.2020.1864364. Epub 2020 Dec 24.

Abstract

The new series of triazole-bearing gramine derivatives were synthesized through a CuAAC procedure. The structures of all newly obtained compounds were confirmed by spectroscopic analysis and DFT methods. The obtained derivatives were screened for their protective potency against oxidative haemolysis induced by free radicals generated from 2,2'-azobis(2-methylpropionamidine) dihydrochloride (AAPH). Our work demonstrates that derivatives with propyl or octyl linker and phthalimide group associated with indole-triazole moiety, which have a folded structure, effectively protect human erythrocytes against oxidative stress-induced haemolysis.

Keywords: Gramine; click reaction; haemolysis; human erythrocytes; indol; oxidative stress.

MeSH terms

  • Amidines / pharmacology
  • Antioxidants* / chemistry
  • Antioxidants* / pharmacology
  • Erythrocytes
  • Hemolysis*
  • Humans
  • Indole Alkaloids
  • Oxidative Stress
  • Triazoles / pharmacology

Substances

  • Amidines
  • Antioxidants
  • Indole Alkaloids
  • Triazoles
  • gramine