Selective delivery of 2-hydroxy APA to Trypanosoma brucei using the melamine motif

Bioorg Med Chem Lett. 2010 Aug 1;20(15):4364-6. doi: 10.1016/j.bmcl.2010.06.070. Epub 2010 Jun 17.

Abstract

Trypanosoma brucei, the parasite that causes human African trypanosomiasis, is auxotrophic for purines and has specialist nucleoside transporters to import these metabolites. In particular, the P2 aminopurine transporter can also selectively accumulate melamine derivatives. In this Letter, we report the coupling of the melamine moiety to 2-hydroxy APA, a potent ornithine decarboxylase inhibitor, with the aim of selectively delivering this compound to the parasite. The best compound described here shows an increased in vitro trypanocidal activity compared with the parent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Humans
  • Ornithine Decarboxylase / metabolism
  • Ornithine Decarboxylase Inhibitors
  • Propylamines / chemical synthesis
  • Propylamines / chemistry*
  • Propylamines / therapeutic use
  • Triazines / chemical synthesis
  • Triazines / chemistry*
  • Triazines / therapeutic use
  • Trypanocidal Agents / chemical synthesis
  • Trypanocidal Agents / chemistry*
  • Trypanocidal Agents / therapeutic use
  • Trypanosoma brucei brucei / drug effects*
  • Trypanosomiasis, African / drug therapy

Substances

  • 2-hydroxy-(aminooxy)propanamine
  • Ornithine Decarboxylase Inhibitors
  • Propylamines
  • Triazines
  • Trypanocidal Agents
  • Ornithine Decarboxylase
  • melamine