Water-Soluble Ruthenium (II) Chiral Heteroleptic Complexes with Amoebicidal in Vitro and in Vivo Activity

J Med Chem. 2017 Feb 9;60(3):899-912. doi: 10.1021/acs.jmedchem.6b00795. Epub 2017 Jan 27.

Abstract

Three water-soluble Ru(II) chiral heteroleptic coordination compounds [Ru(en)(pdto)]Cl2 (1), [Ru(gly)(pdto)]Cl (2), and [Ru(acac)(pdto)]Cl (3), where pdto = 2,2'-[1,2-ethanediylbis-(sulfanediyl-2,1-ethanediyl)]dipyridine, en = ethylendiamine, gly = glycinate, and acac = acetylacetonate, have been synthezised and fully characterized. The crystal structures of compounds 1-3 are described. The IC50 values for compounds 1-3 are within nanomolar range (14, 12, and 6 nM, respectively). The cytotoxicity for human peripheral blood lymphocytes is extremely low (>100 μM). Selectivity indexes for Ru(II) compounds are in the range 700-1300. Trophozoites exposed to Ru(II) compounds die through an apoptotic pathway triggered by ROS production. The orally administration to infected mice induces a total elimination of the parasite charge in mice faeces 1-2-fold faster than metronidazole. Besides, all compounds inhibit the trophozoite proliferation in amoebic liver abscess induced in hamster. All our results lead us to propose these compounds as promising candidates as antiparasitic agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / pharmacology*
  • Antiprotozoal Agents / therapeutic use
  • Apoptosis / drug effects
  • Cells, Cultured
  • Cricetinae
  • Crystallography, X-Ray
  • Entamoeba histolytica / drug effects*
  • Humans
  • Inhibitory Concentration 50
  • Liver Abscess, Amebic / drug therapy
  • Mice
  • Reactive Oxygen Species / metabolism
  • Ruthenium Compounds / chemistry
  • Ruthenium Compounds / pharmacology*
  • Ruthenium Compounds / therapeutic use
  • Stereoisomerism

Substances

  • Antiprotozoal Agents
  • Reactive Oxygen Species
  • Ruthenium Compounds