Synthesis, characterisation and cytotoxic properties of the N1,N4-diarylidene-S-methyl-thiosemicarbazone chelates with Fe(III) and Ni(II)

Eur J Med Chem. 2007 Feb;42(2):161-7. doi: 10.1016/j.ejmech.2006.09.004. Epub 2006 Oct 27.

Abstract

Reactions of 2-hydroxy-3-methoxy, 2-hydroxy-4-methoxy-benzaldehyde with 3- and 4-methoxy-substituted salicylaldehyde S-methyl-thiosemicarbazones in the presence of FeCl(3) and NiCl(2) resulted in the corresponding methoxy-substituted N(1),N(4)-diarylidene-S-methyl-thiosemicarbazone chelates. Characterisation of the compounds in the [Fe(L)Cl] and [Ni(L)] general formula was accomplished by means of elemental analysis, conductivity and magnetic measurements, (1)H NMR, UV-vis, IR and mass spectroscopy. Cytotoxicity and proliferation experiments using K562 chronic myeloid leukemia cell line and ECV 304 human endothelial cell line imply that the iron(III) chelates may have anti-leukemic effects with 3.5 microg/dl LD(50) dose.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Line
  • Chelating Agents / chemical synthesis*
  • Chelating Agents / chemistry
  • Drug Screening Assays, Antitumor
  • Ferric Compounds / chemical synthesis
  • Ferric Compounds / chemistry
  • Ferric Compounds / pharmacology
  • Humans
  • Iron*
  • K562 Cells
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Nickel*
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / pharmacology
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Structure-Activity Relationship
  • Thiosemicarbazones / chemical synthesis*
  • Thiosemicarbazones / chemistry
  • Thiosemicarbazones / pharmacology

Substances

  • Antineoplastic Agents
  • Chelating Agents
  • Ferric Compounds
  • Organometallic Compounds
  • Thiosemicarbazones
  • Nickel
  • Iron