Crystal structure and antitumor activity of the novel zwitterionic complex of tri-n-Butyltin(IV) with 2-thiobarbituric acid

Balas, V.I., Hadjikakou, S.K., Hadjiliadis, N., Kourkoumelis, N., Light, M.E., Hursthouse, M., Metsios, A.K. and Karkabounas, S. (2008) Crystal structure and antitumor activity of the novel zwitterionic complex of tri-n-Butyltin(IV) with 2-thiobarbituric acid. Bioinorganic Chemistry and Applications, 2008. (doi:10.1155/2008/654137).

Abstract

A novel tri-n-butyl(IV) derivative of 2-thiobarbituric acid (HTBA) of formula [(n-Bu)3Sn(TBA) H2O] (1) has been synthesized and characterized by elemental analysis and 119Sn-NMR and FT-IR spectroscopic techniques. The crystal structure of complex 1 has been determined by single crystal X-ray diffraction analysis at 120(2) K. The geometry around Sn(IV) is trigonal bipyramidal. Three n-butyl groups and one oxygen atom from a deprotonated 2-thiobarbituric ligand are bonded to the metal center. The geometry is completed with one oxygen from a water molecule. Compound 1 exhibits potent, in vitro, cytotoxicity against sarcoma cancer cells (mesenchymal tissue) from the Wistar rat, polycyclic aromatic hydrocarbons (PAH, benzo[a]pyrene) carcinogenesis. In addition, the inhibition caused by 1, in the rate of lipoxygenase (LOX) catalyzed oxidation reaction of linoleic acid to hyperoxolinoleic acid, has been also kinetically and theoretically studied. The results are compared to that of cisplatin.

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Contributors

Author: M.E. Light

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