Identification of Adenine and Benzimidazole Nucleosides as Potent Human Concentrative Nucleoside Transporter 2 Inhibitors: Potential Treatment for Hyperuricemia and Gout

J Med Chem. 2016 Apr 28;59(8):3719-31. doi: 10.1021/acs.jmedchem.5b01884. Epub 2016 Apr 11.

Abstract

To test the hypothesis that inhibitors of human concentrative nucleoside transporter 2 (hCNT2) suppress increases in serum urate levels derived from dietary purines, we previously identified adenosine derivative 1 as a potent hCNT2 inhibitor (IC50 = 0.64 μM), but further study was hampered due to its poor solubility. Here we describe the results of subsequent research to identify more soluble and more potent hCNT2 inhibitors, leading to the discovery of the benzimidazole nucleoside 22, which is the most potent hCNT2 inhibitor (IC50 = 0.062 μM) reported to date. Compound 22 significantly suppressed the increase in plasma uric acid levels after oral administration of purine nucleosides in rats. Because compound 22 was poorly absorbed orally in rats (F = 0.51%), its pharmacologic action was mostly limited to the gastrointestinal tract. These findings suggest that inhibition of hCNT2 in the gastrointestinal tract can be a promising approach for the treatment of hyperuricemia.

MeSH terms

  • Adenine / chemistry*
  • Animals
  • Benzimidazoles / chemistry*
  • Gout / drug therapy*
  • Humans
  • Hyperuricemia / drug therapy*
  • Male
  • Membrane Transport Proteins / drug effects*
  • Nucleosides / chemistry
  • Nucleosides / pharmacokinetics
  • Nucleosides / pharmacology*
  • Nucleosides / therapeutic use
  • Rats
  • Rats, Sprague-Dawley

Substances

  • Benzimidazoles
  • Membrane Transport Proteins
  • Nucleosides
  • cif nucleoside transporter
  • Adenine