Enzymatic synthesis of 5-amino quinoline oligomers and evaluation of their free radical scavenging activity

Bilici A., Geçibesler İ. H., Kaya İ.

CANADIAN JOURNAL OF CHEMISTRY, vol.95, no.1, pp.7-15, 2017 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 95 Issue: 1
  • Publication Date: 2017
  • Doi Number: 10.1139/cjc-2016-0210
  • Journal Name: CANADIAN JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.7-15
  • Keywords: enzymatic polymerization, HRP, 5-aminoquinoline, antioxidant activity, DPPH, CONDUCTING POLYMERS, OXIDATIVE POLYMERIZATION, FACILE SYNTHESIS, PHENYLENEDIAMINE, COPOLYMER
  • Çanakkale Onsekiz Mart University Affiliated: Yes

Abstract

The compound 5-aminoquinoline (AQ) was treated with horseradish peroxidase (HRP) and H2O2 in a reaction medium containing a dioxane: phosphate buffer mixture (70:30). Products (OAQ) with a degree of polymerization ranging from 4 to 12 were obtained. H-1 NMR, FTIR, UV-vis, SEM, TG-DTA, DSC, XRD analysis, and conductivity measurements were conducted for characterization of OAQ. Compared with a monomer, OAQ showed higher thermal stability. After heating to 1000 degrees C, 46% of the initial weight of the OAQ remained. The antioxidant efficiencies of the monomer and oligomer were evaluated by the typical spectrophotometric method such as the bleaching of 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals. OAQ showed improved DPPH activity compared with the AQ monomer.