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Aromatic amine N-oxide organometallic compounds: searching for prospective agents against infectious diseases

Esteban Rodríguez Arce1, M Florencia Mosquillo, Leticia Pérez-Díaz

  • 1Cátedra de Química Inorgánica, Departamento Estrella Campos, Facultad de Química, Universidad de la República, Gral. Flores 2124, 11800 Montevideo, Uruguay. dgambino@fq.edu.uy luotero@fq.edu.uy.

Dalton Transactions (Cambridge, England : 2003)
|July 24, 2015
PubMed

Insights

New palladium and platinum compounds show promise as anti-parasitic agents. These novel metal complexes demonstrate high activity against Trypanosoma cruzi and Mycobacterium tuberculosis, with excellent selectivity for T. cruzi.

Area of Science:

  • Coordination Chemistry
  • Medicinal Inorganic Chemistry
  • Computational Chemistry

Background:

  • Development of novel therapeutic agents against infectious diseases is crucial.
  • Metal complexes offer diverse structural and electronic properties for drug design.
  • Previous studies explored metal complexes with pyridine-2-thiolato-1-oxide (mpo) ligands.

Purpose of the Study:

  • To synthesize and characterize novel palladium (Pd) and platinum (Pt) metal complexes incorporating 1,1'-bis(diphenylphosphino)ferrocene (dppf) and mpo ligands.
  • To evaluate the cytotoxic activity and selectivity of these compounds against Trypanosoma cruzi and Mycobacterium tuberculosis (MTB).
  • To investigate the potential mechanism of action, specifically inhibition of T. cruzi NADH-fumarate reductase (TcFR).

Main Methods:

  • Synthesis and full characterization of [M(mpo)(dppf)](PF6) compounds (M = Pd, Pt) using experimental techniques.
  • Density Functional Theory (DFT) computational studies for structural analysis.
  • In vitro cytotoxicity assays against T. cruzi and MTB.
  • Molecular docking studies on T. cruzi NADH-fumarate reductase (TcFR).
  • Experimental confirmation of enzyme inhibition using T. cruzi protein extracts.

Main Results:

  • Isomorphous [M(mpo)(dppf)](PF6) compounds were successfully synthesized and characterized.
  • Both compounds exhibited high cytotoxicity against T. cruzi and MTB, with good to excellent selectivity indices for T. cruzi.
  • The dppf ligand enhanced selectivity towards T. cruzi compared to related complexes.
  • Molecular docking and experimental assays confirmed the compounds as potent inhibitors of T. cruzi NADH-fumarate reductase.

Conclusions:

  • The synthesized palladium and platinum complexes show significant potential as anti-trypanosomal agents.
  • The inclusion of the ferrocene moiety (dppf) is key to improving anti-parasitic selectivity.
  • These compounds warrant further investigation for the development of new treatments against infectious diseases like Chagas disease.

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