Details

Autor(en) / Beteiligte

• Stanojkovic, Tatjana P.
• Kovala-Demertzi, Dimitra
• Primikyri, Alexandra
• Garcia-Santos, Isabel
• Castineiras, Alfonso
• Juranic, Zorica
• Demertzis, Mavroudis A.

Titel

Zinc(II) complexes of 2-acetyl pyridine 1-(4-fluorophenyl)-piperazinyl thiosemicarbazone: Synthesis, spectroscopic study and crystal structures – Potential anticancer drugs

Ist Teil von

• Journal of inorganic biochemistry, 2010-04, Vol.104 (4), p.467-476

Ort / Verlag

United States: Elsevier Inc

Erscheinungsjahr

2010

Quelle

MEDLINE

Beschreibungen/Notizen

• 2-Acetyl pyridine thiosemicarbazone containing an 1-(4-fluorophenyl)-piperazinyl ring incorporated at N(4)-position, HAcPipPheF ( 1) and the Zinc(II) complexes [Zn(AcPipPheF) 2] ( 2) and [Zn(OAc)(AcPipPheF)] 2 ( 3) have been prepared and structurally characterized by means of vibrational and NMR ( 1H and 13C) spectroscopy. The crystal structures of the compounds 1-3 have been determined by X-ray crystallography. Biomedical studies revealed that, compounds 1–3 displayed potent anticancer activity. The antiproliferative activity of 1–3 was found to be considerably stronger than that of cis-platin. The IC 50 values range from 26 to 90 nM, against all cell lines tested, while for cis-platin the IC 50 values range from 2 to 17 μM and for the Zinc salt, ZnCl 2, the IC 50 values range from 81 to 93 μM. The complex 3 shows the highest activity against all four cancer cell lines and the highest selectivity against K562 and MDA-MB-453 cancer cell lines. The compounds inhibited tumor cell proliferation by arresting the cell cycle progression at the S phase. 2-Acetyl pyridine thiosemicarbazone containing an 1-(4-fluorophenyl)-piperazinyl ring incorporated at N(4)-position, HAcPipPheF ( 1) and the zinc(II) complexes [Zn(AcPipPheF) 2] (2) and [Zn(OAc)(AcPipPheF)] 2 ( 3) have been prepared and structurally characterized by means of vibrational and NMR ( 1H and 13C) spectroscopy. The crystal structures of the compounds 1– 3 have been determined by X-ray crystallography. The metal coordination geometry of [Zn(AcPipPheF) 2] is described as distorted octahedral configuration in a trans-N– cis-N– cis-S configuration. In [Zn(OAc)(AcPipPheF)] 2 one of the acetato group exhibits monoatomic bridge and the other bridges in a bidentate manner. The zinc(1) metal ion is coordinated in a distorted octahedral configuration while the metal coordination of Zn(2) is described as distorted square pyramidal. Biomedical studies revealed that, compounds 1– 3 displayed potent anticancer activity. The antiproliferative activity of 1– 3 was found to be considerably stronger than that of cis-platin. The IC 50 values range from 26 to 90 nM, against all cell lines tested, while for cis-platin the IC 50 values range from 2 to 17 μM and for the zinc salt, ZnCl 2, the IC 50 values range from 81 to 93 μM. The complex 3 shows the highest activity against all four cancer cell lines and the highest selectivity against K562 and MDA-MB-453 cancer cell lines. The compounds inhibited tumor cell proliferation by arresting the cell cycle progression at the S phase.