Organotin(IV) complexes of 2-pyridineformamide-derived thiosemicarbazones: antimicrobial and cytotoxic effects

Eur J Med Chem. 2008 Jul;43(7):1454-61. doi: 10.1016/j.ejmech.2007.09.016. Epub 2007 Sep 29.

Abstract

Reaction of n-butyltin trichloride [(n-Bu)SnCl(3)] with 2-pyridineformamide thiosemicarbazone (H2Am4DH) and its N(4)-methyl (H2Am4Me) and N(4)-ethyl (H2Am4Et) derivatives gave [(n-Bu)Sn(2Am4DH)Cl(2)] (1), [(n-Bu)Sn(2Am4Me)Cl(2)] (2), and [(n-Bu)Sn(2Am4Et)Cl(2)] (3). Thiosemicarbazones as well as their tin complexes are active as antimicrobials against the growth of Candida albicans and Salmonella typhimurium and were highly active against malignant glioblastoma. The cytotoxic activity of complexes 1-3 is similar. Among the studied compounds [(n-Bu)Sn(2Am4DH)Cl(2)] (1) was the most active as antiproliferative (cytostatic) agent. Thiosemicarbazones and their tin(IV) complexes proved to be more potent as cytotoxic agents than cisplatin. All the compounds were able to induce apoptosis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology*
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Formamides / chemistry*
  • Humans
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Organotin Compounds / chemistry*
  • Pyridines / chemistry*
  • Thiosemicarbazones / chemistry*
  • Thiosemicarbazones / pharmacology*
  • X-Ray Diffraction

Substances

  • 2-pyridineformamide
  • Anti-Infective Agents
  • Antineoplastic Agents
  • Formamides
  • Organotin Compounds
  • Pyridines
  • Thiosemicarbazones