Benzophenone derivatives as cysteine protease inhibitors and biological activity against Leishmania(L.) amazonensis amastigotes

Biomed Pharmacother. 2015 Oct:75:93-9. doi: 10.1016/j.biopha.2015.08.030. Epub 2015 Sep 20.

Abstract

The leishmanicidal potential of benzophenones has been described, some of them highlighting their potential as cysteine protease inhibitors. Therefore, this work described leishmanicidal activity of nine benzophenone derivatives (1a-c;2a-c;3a-c) against intramacrophage amastigote forms of Leishmania(L.)amazonensis (IC50) and the cytotoxic effect on murine peritoneal macrophages (CC50). The derivative 1c exhibited a selectivity index SI (CC50/IC50) of 6.7, besides cytotoxicity lower than Amphotericin B (p< 0.05). Moreover it showed inhibitory activity against papain (42.8±0.3, p<0.05), and when tested on trypanosomatids cysteine proteases 1c also proved to be a potent inhibitor of rCPB2.8, rCPB3.0 and cruzain, showing non-competitive inhibition mechanism by enzymatic assays in vitro.So, benzophenone 1c is interesting drug candidate prototype, with a multi-target directed mode of action, inhibiting rCPB2.8, rCPB3.0 and cruzain.

Keywords: Benzophenone derivatives; Cysteine proteases; Leishmania amazonensis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzophenones / metabolism
  • Benzophenones / pharmacology*
  • Binding, Competitive
  • Cell Survival / drug effects
  • Cells, Cultured
  • Cysteine Endopeptidases / metabolism*
  • Cysteine Proteinase Inhibitors / metabolism
  • Cysteine Proteinase Inhibitors / pharmacology*
  • Dose-Response Relationship, Drug
  • Kinetics
  • Leishmania / drug effects*
  • Leishmania / enzymology
  • Leishmania / growth & development
  • Macrophages, Peritoneal / drug effects*
  • Macrophages, Peritoneal / pathology
  • Mice
  • Papain / antagonists & inhibitors
  • Papain / metabolism
  • Protein Binding
  • Protozoan Proteins / antagonists & inhibitors*
  • Protozoan Proteins / metabolism
  • Trypanocidal Agents / metabolism
  • Trypanocidal Agents / pharmacology*

Substances

  • Benzophenones
  • Cysteine Proteinase Inhibitors
  • Protozoan Proteins
  • Trypanocidal Agents
  • benzophenone
  • Cysteine Endopeptidases
  • Papain