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Bioinorganic Chemistry and Applications
Volume 2010 (2010), Article ID 867195, 9 pages
http://dx.doi.org/10.1155/2010/867195
Research Article

Diorganotin Complexes of a Thiosemicarbazone, Synthesis: Properties, X-Ray Crystal Structure, and Antiproliferative Activity of Diorganotin Complexes

1Sector of Inorganic and Analytical Chemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece
2Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie Street, 50-383 Wrocław, Poland
3Institute of Organic and Pharmaceutical Chemistry, National Hellenic Research Foundation, Vas. Constantinou 48, 11635 Athens, Greece

Received 8 February 2010; Accepted 31 March 2010

Academic Editor: Spyros Perlepes

Copyright © 2010 Joanna Wiecek et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

The synthesis and spectral characterization of novel diorganotin complexes with 3-hydroxypyridine-2-carbaldehyde thiosemicarbazone, H 𝟐 L (1), [ S n M e 2 (L)] (2), [ S n B u 2 (L)] (3), and [ S n P h 2 (L)] (4) are reported. The single-crystal X-ray structure of complex [ S n P h 2 (L)(DMSO)] (5) shows that the ligand is doubly deprotonated and is coordinated as tridentate ligand. The six coordination number is completed by two carbon atoms of phenyl groups. There are two similar monomers 5a (Sn1) and 5b (Sn51) in the asymmetric unit. The monomers 5a and 5b are linked through intermolecular hydrogen bonds of N–H–O and C–H–S type. C - H → 𝜋 , intermolecular interactions, intra- and intermolecular hydrogen bonds stabilize this structure and leads to aggregation and a supramolecular assembly. The IR and NMR ( 1 H , 1 3 C and 1 1 9 S n ) spectroscopic data of the complexes are reported. The in vitro cytotoxic activity has been evaluated against the cells of three human cancer cell lines: MCF-7 (human breast cancer cell line), T-24 (bladder cancer cell line), A-549 (nonsmall cell lung carcinoma) and a mouse L-929 (a fibroblast-like cell line cloned from strain L). Compounds 1, 3, and 4 were found active against all four cell lines. Selectivity was observed for complexes 3 and 4 which were found especially active against MCF-7 and T-24 cancer cell lines.