A computer-assisted discovery of novel potential anti-obesity compounds as selective carbonic anhydrase VA inhibitors

Eur J Med Chem. 2019 Nov 1:181:111565. doi: 10.1016/j.ejmech.2019.111565. Epub 2019 Jul 27.

Abstract

The human Carbonic anhydrases (hCA) VA and VB play a key role in ureagenesis, gluconeogenesis, lipogenesis and in the metabolism regulation, thus representing highly popular drug targets. Albeit several hCA inhibitors have been designed and are currently in clinical use, serious drug interactions have been reported due to their poor selectivity. In this perspective, the drug repurposing approach could be a useful tool in order to investigate the drug promiscuity/polypharmacology profile. In this study, virtual screening techniques and in vitro assays were combined to identify novel selective hCA VA inhibitors from among around 94000 compounds. The docking analysis highlighted 12 promising best hits, biologically characterized in terms of their hCA VA inhibitory activity. Interestingly, among them, the anticancer agents fludarabine and lenvatinib and the antiepileptic rufinamide were able to selectively inhibit the enzyme activity in the micromolar range, while a pyrido-indole derivative, the homovanillic acid sulfate and the desacetyl metabolite of the antibacterial cephapirin in the nanomolar range.

Keywords: Carbonic anhydrase; Drug repurposing; Isoform-selective inhibitors; Obesity; Virtual screening.

MeSH terms

  • Anti-Obesity Agents / chemistry
  • Anti-Obesity Agents / pharmacology*
  • Carbonic Anhydrase I / antagonists & inhibitors
  • Carbonic Anhydrase I / metabolism
  • Carbonic Anhydrase II / antagonists & inhibitors
  • Carbonic Anhydrase II / metabolism
  • Carbonic Anhydrase Inhibitors / chemistry
  • Carbonic Anhydrase Inhibitors / pharmacology*
  • Computer-Aided Design
  • Drug Discovery
  • Drug Repositioning*
  • Humans
  • Molecular Docking Simulation
  • Obesity / drug therapy*
  • Obesity / metabolism

Substances

  • Anti-Obesity Agents
  • Carbonic Anhydrase Inhibitors
  • Carbonic Anhydrase I
  • Carbonic Anhydrase II