Synthesis, structural characterization and biological studies of the triphenyltin(IV) complex with 2-thiobarbituric acid (Journal article)

Balas, V. I./ Verginadis, I. I./ Geromichalos, G. D./ Kourkoumelis, N./ Male, L./ Hursthouse, M. B./ Repana, K. H./ Yiannaki, E./ Charalabopoulos, K./ Bakas, T./ Hadjikakou, S. K.


The reaction between 2-thiobarbituric acid (H(2)TBA), which was treated with an equimolar amount of potassium hydroxide, in a water with triphenytin chloride in methanol, results in the formation of the {[Ph3Sn(O-HTBA)]}(n) (1) complex. Crystals of the hydrated 1 with formula {[Ph3Sn(O-HTBA)]center dot 0.7(H2O)}(n) were growth from methanol/acetonitrile solution, of the white precipitation, filtered off, from the reaction. The crystal structure of complex 1 has been determined by X-ray diffraction at 120K. Complex 1 is polymeric. The geometry around the tin(IV) ions is trigonal bi-pyramidal with coordination to three C atoms from phenyl groups and one O atom from a de-protonated HTBA ligand. Complex 1 and the already known [(n-Bu)(3)Sn(O-HTBA)center dot H2O] (2) were evaluated for their in vitro cytotoxic activity (cell viability) against human cancer cell lines: HeLa (cervical), OAW-42 (ovarian), MCF-7 (breast, ER positive), MDA-MB-231 (breast, ER negative), A549 (lung), Caki-1 (renal) and additionally, the normal human lung cell line MRC-5 (normal human fetal lung fibroblast cells) and normal immortalized human mammary gland epithelial cell line MTSV17 with a Trypan Blue assay. Moreover complex I was evaluated for its in vitro cell growth proliferation activity against leiomyosarcoma cells (LMS), MCF-7 and MRC-5 cells with a Thiazolyl Blue Tetrazolium Bromide (MU) assay. The type of cell death caused by complexes 1 and 2 was also evaluated by use of flow cytometry assay. The results showed that these compounds mediate a strong cytotoxic response to normal and cancer cell lines tested through apoptosis and induce cell cycle arrest in S phase of the cell cycle, suggesting DNA intercalation (direct or indirect) with the complexes. Finally, the influence of these complexes 1 and 2 upon the catalytic peroxidation of linoleic acid to hydroperoxylinoleic acid by the enzyme lipoxygenase (LOX) was kinetically and theoretically studied. (C) 2011 Elsevier Masson SAS. All rights reserved.
Institution and School/Department of submitter: Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας
Keywords: bioinorganic chemistry,organotin(iv) complexes,crystal structures,cytotoxic activity,in-vitro cytotoxicity,organotin(iv) complexes,color immunofluorescence,apoptosis,ligands,assay,thioamides,crystal,5-chloro-2-mercaptobenzothiazole,2-mercaptobenzothiazole
URI: http://olympias.lib.uoi.gr/jspui/handle/123456789/9519
ISSN: 0223-5234
Link: <Go to ISI>://000291895200020
http://ac.els-cdn.com/S022352341100290X/1-s2.0-S022352341100290X-main.pdf?_tid=fba21f55c15427636e24fd814221bea3&acdnat=1333030084_48c3d5242640c0a71fd4def3231d48a7
Publisher: Elsevier
Appears in Collections:Άρθρα σε επιστημονικά περιοδικά ( Ανοικτά)

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