Synthesis, characterization and evaluation of antileishmanial activity of copper(II) with fluorinated α-hydroxycarboxylate ligands

Biometals. 2009 Dec;22(6):1095-101. doi: 10.1007/s10534-009-9260-1.

Abstract

In this study, Cu(II) complexes with fluorinated ligands were produced aiming at the development of new, less toxic antileishmanial metallodrugs. Complexes of the general formula CuL2 (L = lactate, trifluorolactate, 2-hydroxyisobutyrate, trifluoro-2-hydroxyisobutyrate) were synthesized in methanolic medium, purified by crystallization and characterized by elemental analysis and electronic and infrared spectroscopies. In vitro experiments with Leishmania amazonensis promastigotes showed that the trifluorolactate derivative more active than its non-fluorinated counterpart. Our results indicate that fluorinated chelators may be interesting to increase metal toxicity and/or open new paths for metallodrug chemotherapy against leishmaniasis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiprotozoal Agents / analysis*
  • Antiprotozoal Agents / chemical synthesis*
  • Antiprotozoal Agents / therapeutic use
  • Cell Culture Techniques
  • Copper / chemistry*
  • Dose-Response Relationship, Drug
  • Electron Spin Resonance Spectroscopy
  • Fluorides / chemistry*
  • Halogenation
  • Hydroxybutyrates / chemistry
  • Inhibitory Concentration 50
  • Lactic Acid / chemistry
  • Leishmania / drug effects*
  • Leishmania / growth & development
  • Leishmaniasis / drug therapy
  • Ligands
  • Molecular Structure
  • Spectrophotometry, Infrared

Substances

  • Antiprotozoal Agents
  • Hydroxybutyrates
  • Ligands
  • Lactic Acid
  • Copper
  • 2-hydroxyisobutyric acid
  • Fluorides