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

Stanojkovic, T. P./ Kovala-Demertzi, D./ Primikyri, A./ Garcia-Santos, I./ Castineiras, A./ Juranic, Z./ Demertzis, M. A.


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 ((1)H and (13)C) 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 mu M and for the zinc salt, ZnCl(2), the IC(50) values range from 81 to 93 mu M. 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. (C) 2010 Elsevier Inc. All rights reserved.
Institution and School/Department of submitter: Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας
Keywords: zn(ii),complexes,thiosemicarbazone,crystal structure,in vitro antitumor activity,biological evaluation,rapid colorimetric assay,antitumor-activity,palladium(ii) complexes,platinum(ii) complexes,spectral properties,metal-complexes,in-vitro
URI: http://olympias.lib.uoi.gr/jspui/handle/123456789/9878
ISSN: 0162-0134
Link: <Go to ISI>://000274921200014
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