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Article << Previous     |     Next >>   Contents Vol 65(12)

Structural and In Vitro Biological Studies of Organotin(iv) Precursors; Selective Inhibitory Activity Against Human Breast Cancer Cells, Positive to Estrogen Receptors

Vasilis I. Balas A , Christina N. Banti A B , Nikolaos Kourkoumelis C , Sotiris K. Hadjikakou A H , George D. Geromichalos D , Despina Sahpazidou D , Louise Male E , Mike B. Hursthouse E , Barbara Bednarz A F , Maciej Kubicki F , Konstantinos Charalabopoulos B G and Nick Hadjiliadis A H

A Section of Inorganic and Analytical Chemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece.
B Department of Experimental Physiology, Medical School, University of Ioannina, 45110 Ioannina, Greece.
C Medical Physics Laboratory, Medical School, University of Ioannina, 45110 Ioannina, Greece.
D Cell Culture, Molecular Modeling and Drug Design Laboratory, Symeonidion Research Center, Theagenion Cancer Hospital, 54007 Thessaloniki, Greece.
E Department of Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, UK.
F Department of Chemistry, Adam Mickiewicz University, ul. Grunwaldzka 6, 60-780 Poznan, Poland.
G Department of Physiology, Democritus University Medical School, 68100 Alexandroupolis, Greece.
H Corresponding authors. Email: shadjika@uoi.gr, nhadjis@uoi.gr

Australian Journal of Chemistry 65(12) 1625-1637 http://dx.doi.org/10.1071/CH12448
Submitted: 28 September 2012  Accepted: 24 October 2012   Published: 26 November 2012


 
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Abstract

Crystals of Ph3SnCl (1) were grown from a methanol/acetonitrile solution. Compounds [Ph3SnOH]n (2) and [(Ph2Sn)4Cl2O2(OH)2] (3) were crystallized from diethyl ether/methanol/acetonitrile and hot acetone/water solutions respectively, of the white precipitation, formed by adding KOH to solutions of 1 and [Ph2SnCl2] in 1 : 1 and 1 : 2 molar ratios respectively. Complex 1 was characterized by X-ray crystallography. X-ray structure determination of compounds 2 and 3 confirmed the previously reported identities. The molecular structure of 1, reported here, is a new polymorphic form of the known one for Ph3SnCl. Four independent [Ph3SnCl] molecules constitute the crystal structure of 1. The moieties are packed in two pairs in a tail-to-tail arrangement.

Complexes 13 were evaluated for their in vitro cytotoxic activity (cell viability) against human cancer cell lines: HeLa (human cervical), MCF-7 (breast, estrogen receptor (ER) positive), MDA-MB-231 (breast, ER negative), A549 (lung), Caki-1 (kidney carcinoma), 786-O (renal adenocarcinoma), K1 (thyroid carcinoma), and the normal human lung cell line MRC-5 (normal human fetal lung fibroblast cells) versus, the normal immortalized human mammary gland epithelial cell line MTSV17 with a sulforhodamine B (SRB) assay. The results show potent cytotoxic activity of the complexes against all cell lines used, which was superior to that of cisplatin (CDDP). Compounds 13 showed higher activity against breast cancer cells MCF-7 (ER positive) than against of MDA-MB-231 (ER negative). These findings prompted us to search for possible interaction of these complexes with other cellular elements of fundamental importance in cell proliferation. The influence of these complexes 13 upon the catalytic peroxidation of linoleic acid to hydroperoxylinoleic acid by the enzyme lipoxygenase (LOX), as well as their binding affinity towards calf thymus-DNA, were kinetically and theoretically studied.





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