Comparative solution equilibrium study of the interactions of copper (II), iron(II) and zinc(II) with triapine (3-Aminopyridine-2-carbaldehyde thiosemicarbazone) and related ligands

E. Enyedy, N. Nagy, Éva Zsigó, Christian R. Kowol, Vladimir B. Arion, Bernhard K. Keppler, T. Kiss

Research output: Contribution to journalArticle

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Abstract

The interactions of CuII, ZnII and FeII with Triapine (3-amino-pyridine-2-carbaldehyde thiosemicarbazone), which is currently undergoing phase II clinical trials as a chemotherapeutic antitumour agent, were investigated in a water/DMSO mixture. The proton-dissociation constants of the ligands, the stability constants and the coordination modes of the metal complexes formed were determined by pH-potentiometric, UV/Vis spectrophotometric, EPR, 1H NMR spectroscopic and ESI-MS methods. Two N-terminally dimethylated derivatives of Triapine were also studied. Mono- and bis-ligand complexes in different protonation states were identified. Furthermore, the formation of the dinuclear species [Cu2L 3]+ was confirmed for all ligands by EPR spectroscopy and ESIMS measurements. The results showed that the N-terminally dimethylated ligands are much more potent chelators than Triapine for the divalent metal ions studied. All three ligands formed the least stable complexes with Zn II, whereas the FeII complexes were somewhat more stable than the corresponding CuII species.

Original languageEnglish
Pages (from-to)1717-1728
Number of pages12
JournalEuropean Journal of Inorganic Chemistry
Issue number11
DOIs
Publication statusPublished - Apr 2010

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Thiosemicarbazones
Zinc
Copper
Iron
Ligands
Paramagnetic resonance
Protonation
Coordination Complexes
Chelating Agents
Dimethyl Sulfoxide
Antineoplastic Agents
Metal ions
3-aminopyridine
3-aminopyridine-2-carboxaldehyde thiosemicarbazone
Protons
Nuclear magnetic resonance
Spectroscopy
Derivatives
Water

Keywords

  • Antitumor agents
  • Epr spectroscopy
  • Stability constants
  • Thiosemicarbazones
  • Transition metals

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Comparative solution equilibrium study of the interactions of copper (II), iron(II) and zinc(II) with triapine (3-Aminopyridine-2-carbaldehyde thiosemicarbazone) and related ligands. / Enyedy, E.; Nagy, N.; Zsigó, Éva; Kowol, Christian R.; Arion, Vladimir B.; Keppler, Bernhard K.; Kiss, T.

In: European Journal of Inorganic Chemistry, No. 11, 04.2010, p. 1717-1728.

Research output: Contribution to journalArticle

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