Synthesis, antioxidant and carbonic anhydrase inhibitory properties of monopeptide-anthraquinone conjugates


KÜÇÜKBAY H. , Parladi F. M. , Kucukbay F. Z. , Angeli A., Bartolucci G., Supuran C. T.

ORGANIC COMMUNICATIONS, vol.14, no.3, pp.255-269, 2021 (Journal Indexed in ESCI) identifier

  • Publication Type: Article / Article
  • Volume: 14 Issue: 3
  • Publication Date: 2021
  • Doi Number: 10.25135/acg.oc.108.2107.2126
  • Title of Journal : ORGANIC COMMUNICATIONS
  • Page Numbers: pp.255-269
  • Keywords: Anthraquinone derivatives, monopeptide anthraquinone conjugates, carbonic anhydrase inhibition, antioxidant activity, DIOXIDE HYDRATION ACTIVITY, AMINO-ACID, DNA-BINDING, DERIVATIVES, CYTOTOXICITY

Abstract

Novel monopeptide-anthraquinone conjugates (1-16) were synthesized by the reaction of appropriate N-protected amino acid with 2-hydroxymethylanthraquinone in good or high yields. The structural elucidation of the new compounds was accomplished by H-1 NMR, C-13 NMR, MS, FT-IR spectroscopy and elemental analysis techniques. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was determined against two human (h) isoforms, hCA I and hCA II. While three of the sixteen compounds showed moderate in vitro carbonic anhydrase inhibitory properties against hCA II with inhibition constants in the micromolar level (43.5, 67.4 and 78.1 mu M), they did not show inhibitory activity against hCA I up to 100 mu M concentration. The antioxidant abilities of the compounds were determined using the 1,1-diphenyl-2-picrylhydrazil (DPPH) radical scavenging method, ferric ion reducing assay and metal chelation methods. While a small amount of antioxidant activity was observed according to the DPPH and ferric ion reducing power assay methods, none of the compounds showed antioxidant properties according to the metal chelating activity method at the concentrations studied.