Water soluble cationic trans-platinum complexes which induce programmed cell death in the protozoan parasite Leishmania infantum

J Inorg Biochem. 2005 Mar;99(3):727-36. doi: 10.1016/j.jinorgbio.2004.12.008. Epub 2005 Jan 1.

Abstract

We have evaluated the cytotoxic properties against the protozoan Leishmania infantum of four water soluble cationic trans-Pt(II)Cl(2) compounds containing as inert groups NH3 and piperazine (1), 4-picoline and piperazine (2), n-butylamine and piperazine (3), and NH3 and 4-piperidino-piperidine (4). The leishmanicidal activity of compounds 3 and 4 against promastigotes of the parasite Leishmania infantum was 2.5- and 1.6-times higher than that of the cytotoxic drug cis-diamminedichloroplatinum(II), respectively. Interestingly, compounds 3 and 4 produce in Leishmania infantum promastigotes a higher amount of programmed cell death than cisplatin, which is associated with cell cycle arrest in G2/M. In contrast to cis-diamminedichloroplatinum(II), binding of compounds 3 and 4 to calf thymus DNA induces conformational changes more similar to those of trans-diamminedichloroplatinum(II) that may be attributed to denaturation of the double helix. Similarly to cis-diamminedichloroplatinum(II) and trans-diamminedichloroplatinum(II), the interaction of compounds 3 and 4 with ubiquitin results in an increase of the alpha-helix content of the protein as observed by circular dichroism spectroscopy. However, fluorescence studies indicate that compounds 3 and 4 produce a decrease in the fluorescence of the tyrosine 59 residue of ubiquitin higher than both cis-diamminedichloroplatinum(II) and trans-diamminedichloroplatinum(II). Altogether, our results suggest that the biochemical mechanism of cytotoxic activity of compounds 3 and 4 against Leishmania infantum must be different from that of cis-diamminedichloroplatinum(II). To the best of our knowledge, compounds 3 and 4 are the first reported trans-platinum complexes that show antiparasitic activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Apoptosis* / drug effects
  • Binding Sites
  • Butylamines / chemistry
  • Butylamines / pharmacology
  • Cations
  • Cisplatin / chemistry
  • Cisplatin / pharmacology
  • DNA / chemistry
  • Leishmania infantum / drug effects*
  • Leishmania infantum / metabolism
  • Molecular Sequence Data
  • Picolines / chemistry
  • Picolines / pharmacology
  • Piperazine
  • Piperazines / chemistry
  • Piperazines / pharmacology
  • Piperidines / chemistry
  • Piperidines / pharmacology
  • Platinum Compounds / chemistry*
  • Platinum Compounds / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tumor Cells, Cultured
  • Ubiquitin / chemistry
  • Water / chemistry*

Substances

  • Antineoplastic Agents
  • Butylamines
  • Cations
  • Picolines
  • Piperazines
  • Piperidines
  • Platinum Compounds
  • Ubiquitin
  • Water
  • Piperazine
  • piperidine
  • DNA
  • calf thymus DNA
  • n-butylamine
  • Cisplatin