Zinc-oxaprozin compounds: Synthesis, structure and biological activity

J Inorg Biochem. 2019 Jun:195:101-110. doi: 10.1016/j.jinorgbio.2019.03.016. Epub 2019 Mar 21.

Abstract

Four novel zinc complexes, namely [Zn(oxa)2(MeOH)4] (1), [Zn(oxa)2(H2O)(bipy)]·MeOH·2.5H2O (2·MeOH·2.5H2O), [Zn(oxa)2(bipyam)]·1.25MeOH (3·1.25MeOH) and [Zn(oxa)2(phen)] (4), with the non-steroidal anti-inflammatory drug oxaprozin (Hoxa) and a N,N'-donor heterocyclic ligand, such as 2,2'‑bipyridylamine (bipyam), 1,10‑phenanthroline (phen) or 2,2'‑bipyridine (bipy), were characterized with physicochemical techniques, various spectroscopies and single-crystal X-ray crystallography. In these coordination compounds, the oxaprozin ligands are coordinated to zinc ion in a monodentate or a bidentate chelating binding mode. The antioxidant activity of the complexes was evaluated via their ability to scavenge in vitro 1,1‑diphenyl‑2‑picrylhydrazyl, hydroxyl and 2,2'‑azinobis‑(3‑ethylbenzothiazoline‑6‑sulfonic acid) radicals. The complexes bind to calf-thymus DNA via intercalation as suggested via a series of studies employing UV-vis spectroscopy, DNA-viscosity measurements and competition with ethidium bromide. The complexes may bind to serum albumins tightly and reversibly in order to get transferred through the bloodstream.

Keywords: DNA-binding; Interaction with albumins; Oxaprozin; Scavenging ability; Structures; Zinc complexes.

MeSH terms

  • Animals
  • Cattle
  • Coordination Complexes / chemical synthesis
  • Coordination Complexes / chemistry*
  • Coordination Complexes / metabolism
  • DNA / chemistry
  • Free Radical Scavengers / chemical synthesis
  • Free Radical Scavengers / chemistry*
  • Free Radical Scavengers / metabolism
  • Humans
  • Intercalating Agents / chemical synthesis
  • Intercalating Agents / chemistry*
  • Intercalating Agents / metabolism
  • Ligands
  • Molecular Structure
  • Oxaprozin / analogs & derivatives*
  • Oxaprozin / metabolism
  • Serum Albumin, Bovine / metabolism
  • Serum Albumin, Human / metabolism
  • Zinc / chemistry

Substances

  • Coordination Complexes
  • Free Radical Scavengers
  • Intercalating Agents
  • Ligands
  • Serum Albumin, Bovine
  • DNA
  • calf thymus DNA
  • Zinc
  • Oxaprozin
  • Serum Albumin, Human