Synthesis and characterization of platinum-sterol hydrazone complexes with biological activity against Leishmania (L.) mexicana

J Inorg Biochem. 2008 Mar;102(3):547-54. doi: 10.1016/j.jinorgbio.2007.11.002. Epub 2007 Nov 19.

Abstract

Leishmaniasis is a parasitic zoonosis caused by protozoans of the genus Leishmania transmitted by insects known as phlebotomines, which are found in wild or urban environments. The disease occurs in tropical and sub-tropical areas, mainly in Asia, Europe, Africa and the Americas. At present, there is no effective treatment for this disease. In the search for new rational chemotherapeutic alternatives, two novel trans [Pt(Hpy1)(2)(Cl)(2)] (1) and trans [Pt(Hpy2)(2) (Cl)(2)] (2) complexes were synthesized by the reaction of K(2)PtCl(4) with sterol hydrazone ligands 20-hydrazone-pyridin-2-yl-5alpha-pregnan-3beta-ol (Hpy1) and 22-hydrazone-pyridin-2-yl-chol-5-ene-3beta-ol (Hpy2). These organic compounds are specific inhibitors of sterol methyl transferase (SMT). The new platinum complexes were characterized by a combination of ESI-MS (electrospray ionization-mass spectroscopy), UV-vis, infrared and NMR spectroscopies; elemental analysis and molar conductivity. Promastigotes of Leishmania (L.) mexicana were treated for 48 h with 10 microM of the sterol hydrazones Hpy1 or Hpy2 alone or coordinated to Pt. Hpy1 produced higher leishmanistatic activity than Hpy2 (39% growth inhibition vs. 16%), which significatively increased (71%, p<0.001) when the complex trans-[Pt(Hpy1)(2)(Cl)(2)] was used. This complex represents a new chemotherapeutic alternative to be evaluated in depth in experimental models of leishmaniasis.

MeSH terms

  • Animals
  • Hydrazones / chemistry
  • Hydrazones / pharmacology*
  • Leishmania mexicana / drug effects*
  • Molecular Structure
  • Platinum / chemistry*
  • Platinum Compounds / chemistry
  • Platinum Compounds / pharmacology*
  • Spectrometry, Mass, Electrospray Ionization
  • Sterols / chemistry*

Substances

  • Hydrazones
  • Platinum Compounds
  • Sterols
  • Platinum