Effect of metal ion complexation and chalcogen donor identity on the antiproliferative activity of 2-acetylpyridine N,N-dimethyl(chalcogen)semicarbazones

Kowol, Christian R.; Eichinger, René; Jakupec, Michael A.; Galanski, Markus; Arion, Vladimir B.; Keppler, Bernhard K.

doi:10.1016/j.jinorgbio.2007.07.026

Cited by 75 publications

(94 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…20 For N 4 -disubstituted TSC ligands the E thione and Z thione tautomers are disfavoured (there being no N 4 -H present for H-bonding e.g. HAp44mT), and instead the unusual EZ thiolate zwitterionic tautomer (Scheme 2) is found in TSC ligands derived from 2-acetylpyridine.…”

Section: 17mentioning

confidence: 99%

Biologically active thiosemicarbazone Fe chelators and their reactions with ferrioxamine B and ferric EDTA; a kinetic study

et al. 2012

View full text Add to dashboard Cite

The Fe III abstraction from Fe III /DFO and Fe III /EDTA complex systems by thiosemicarbazone ligands derived from 2-acetylpyridine has been studied from a kinetico-mechanistic perspective at relevant pH conditions and at varying temperatures and buffer solutions. The reactions have been found to be extremely dependent on the dominant E/Z isomeric form of the TSC ligands present in the reaction medium. Consequently the isomerisation processes occurring on the free ligands have also been monitored under equivalent conditions. The isomerisation process is found to be acid dependent, despite the absence of protonation under the conditions used, and presumably proceeds via an azo-type tautomer of the ligand. In all cases the existence of outer-sphere interaction processes has been established, both promoting the reactions and producing dead-end complexes. has also been conducted with significant differences in the kinetic features that implicate keystone outer-sphere interactions which dominate reactivity, even with isomeric forms that are not the best suited for direct complexation.

show abstract

Section: 17mentioning

confidence: 99%

Biologically active thiosemicarbazone Fe chelators and their reactions with ferrioxamine B and ferric EDTA; a kinetic study

et al. 2012

View full text Add to dashboard Cite

show abstract

“…However, they exhibited only moderate to low cytotoxicity (IC 50  100 µM in CH1 cell line for the copper(II) complexes, >300 µM for the free ligands), when compared with other HCTs that showed IC 50 values in the nanomolar range. 50,51,52 This low cytotoxicity is presumably caused by the very low lipophilicity of these compounds, which may hinder cell membrane passage.…”

Section: Introductionmentioning

confidence: 99%

Effects of Terminal Dimethylation and Metal Coordination of Proline-2-formylpyridine Thiosemicarbazone Hybrids on Lipophilicity, Antiproliferative Activity, and hR2 RNR Inhibition

et al. 2014

Self Cite

View full text Add to dashboard Cite

The nickel(II), copper(II) and zinc(II) complexes of the proline-thiosemicarbazone hybrids 3-methyl-(S)-pyrrolidine-2-carboxylate-2-formylpyridine thiosemicarbazone (L-Pro-FTSC or (S)-H 2 L 1 ) and 3-methyl-(R)-pyrrolidine-2-carboxylate-2-formylpyridine thiosemicarbazonehave been synthesized and characterized by elemental analysis, one-and two-dimensional 1 H and 13 C NMR spectroscopy, CD, UV−vis and ESI mass spectrometry. Compounds 13, 6 and 7 have been also studied by single crystal X-ray diffraction. Magnetic properties and solid state high-field EPR spectra of 2 over the range 50420 GHz were investigated. The complex formation processes of L-Pro-FTSC with nickel(II) and zinc(II) have been studied in aqueous solution due to the excellent water solubility of the complexes via pH-potentiometry, UV−vis and 1 H NMR spectroscopy. The results of the antiproliferative activity in vitro showed that dimethylation improves the cytotoxicity and hR2 RNR inhibition. Therefore introduction of more lipophilic groups into thiosemicarbazone-proline backbone becomes an option for the synthesis of more efficient cytotoxic agents of this family of compounds.3

show abstract

“…In contrast, there are only few studies on selenosemicarbazones which showed a greater biological activity in comparison to sulphur analogues [7][8][9][10][11][12][13]. Surprisingly, to the best of our knowledge there is just one study on antiproliferative activity of a selenosemicarbazone complex [13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of new Pt(II) and Pd(II) complexes with 2-quinolinecarboxaldehyde selenosemicarbazone: Cytotoxic activity evaluation of Cd(II), Zn(II), Ni(II), Pt(II) and Pd(II) complexes with heteroaromatic selenosemicarbazones

Gligorijević

Todorović

Radulović

et al. 2009

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

Effect of metal ion complexation and chalcogen donor identity on the antiproliferative activity of 2-acetylpyridine N,N-dimethyl(chalcogen)semicarbazones

Cited by 75 publications

References 28 publications

Biologically active thiosemicarbazone Fe chelators and their reactions with ferrioxamine B and ferric EDTA; a kinetic study

Biologically active thiosemicarbazone Fe chelators and their reactions with ferrioxamine B and ferric EDTA; a kinetic study

Effects of Terminal Dimethylation and Metal Coordination of Proline-2-formylpyridine Thiosemicarbazone Hybrids on Lipophilicity, Antiproliferative Activity, and hR2 RNR Inhibition

Synthesis and characterization of new Pt(II) and Pd(II) complexes with 2-quinolinecarboxaldehyde selenosemicarbazone: Cytotoxic activity evaluation of Cd(II), Zn(II), Ni(II), Pt(II) and Pd(II) complexes with heteroaromatic selenosemicarbazones

Contact Info

Product

Resources

About