Synthesis, characterization and in vitro biological evaluation of novel organotin(IV) compounds with derivatives of 2-(5-arylidene-2,4-dioxothiazolidin-3-yl)propanoic acid
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Zmejkovski, Bojana B.
Wessjohann, Ludger A.
Kaludjerović, Goran N.
Article (Published version)
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Two novel triphenyltin(IV) compounds, [Ph(3)SnL1] (L1 = 2-(5-(4- fluorobenzylidene)-2,4-dioxotetrahydrothiazole-3-yl)propanoate (1)) and [Ph(3)SnL2] (L2 = 2-(5-(5-methyl-2-furfurylidene)-2,4-dioxotetrahydrothiazole-3-yl)propanoate (2)) were synthesized and characterized by FT-IR, (H-1 and C-13) NMR spectroscopy, mass spectrometry, and elemental microanalysis. The in vitro anticancer activity of the synthesized organotin(IV) compounds was determined against four tumor cell lines: PC-3 (prostate), HT-29 (colon), MCF-7 (breast), and HepG2 (hepatic) using MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-12 diphenyltetrazolium bromide) and CV (crystal violet) assays. The IC50 values are found to be in the range from 0.11 to 0.50 mu M. Compound 1 exhibits the highest activity toward PC-3 cells (IC50 = 0.115 +/- 0.009 mu M; CV assay). The tin and platinum uptake in PC-3 cells showed a threefold lower uptake of tin in comparison to platinum (as cisplatin). Together with its higher activity this indicates... a much higher cell inhibition potential of the tin compounds (calculated to ca. 50 to 100 times). Morphological analysis suggested that the compounds induce apoptosis in PC-3 cells, and flow cytometry analysis revealed that 1 and 2 induce autophagy as well as NO (nitric oxide) production.
Keywords:Tin(IV) / In vitro / Prostate cancer / Apoptosis / Autophagy / NO
Source:Journal of Inorganic Biochemistry, 2020, 211
- Elsevier Science Inc, New York
Funding / projects:
- National Scholarship for Postdoctoral Studies of the Republic of Serbia
- German Academic Exchange Service (DAAD)Deutscher Akademischer Austausch Dienst (DAAD) 
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
- Neuroendocrine control of growth hormone secretion in humans - new challenges. Control of energy homeostasis in humans in various pathological conditions. Genetics in familial pituitary tumorigenesis. Clinical-pathological correlations in atypical pituit (RS-175033)