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
Authorized Users Only
2020
Authors
Pantelić, NebojšaZmejkovski, Bojana B.
Božić, Bojan
Dojčinović, Biljana
Banjac, Nebojša
Wessjohann, Ludger A.
Kaludjerović, Goran N.
Article (Published version)
Metadata
Show full item recordAbstract
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 / NOSource:
Journal of Inorganic Biochemistry, 2020, 211Publisher:
- 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) [57448219]
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-MESTD-Basic Research (BR or ON)-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-MESTD-Basic Research (BR or ON)-175033)
DOI: 10.1016/j.jinorgbio.2020.111207
ISSN: 0162-0134
PubMed: 32801055
WoS: 000566344500012
Scopus: 2-s2.0-85089264363
Collections
Institution/Community
Poljoprivredni fakultetTY - JOUR AU - Pantelić, Nebojša AU - Zmejkovski, Bojana B. AU - Božić, Bojan AU - Dojčinović, Biljana AU - Banjac, Nebojša AU - Wessjohann, Ludger A. AU - Kaludjerović, Goran N. PY - 2020 UR - http://aspace.agrif.bg.ac.rs/handle/123456789/5306 AB - 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. PB - Elsevier Science Inc, New York T2 - Journal of Inorganic Biochemistry T1 - 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 VL - 211 DO - 10.1016/j.jinorgbio.2020.111207 ER -
@article{ author = "Pantelić, Nebojša and Zmejkovski, Bojana B. and Božić, Bojan and Dojčinović, Biljana and Banjac, Nebojša and Wessjohann, Ludger A. and Kaludjerović, Goran N.", year = "2020", abstract = "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.", publisher = "Elsevier Science Inc, New York", journal = "Journal of Inorganic Biochemistry", title = "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", volume = "211", doi = "10.1016/j.jinorgbio.2020.111207" }
Pantelić, N., Zmejkovski, B. B., Božić, B., Dojčinović, B., Banjac, N., Wessjohann, L. A.,& Kaludjerović, G. N.. (2020). 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. in Journal of Inorganic Biochemistry Elsevier Science Inc, New York., 211. https://doi.org/10.1016/j.jinorgbio.2020.111207
Pantelić N, Zmejkovski BB, Božić B, Dojčinović B, Banjac N, Wessjohann LA, Kaludjerović GN. 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. in Journal of Inorganic Biochemistry. 2020;211. doi:10.1016/j.jinorgbio.2020.111207 .
Pantelić, Nebojša, Zmejkovski, Bojana B., Božić, Bojan, Dojčinović, Biljana, Banjac, Nebojša, Wessjohann, Ludger A., Kaludjerović, Goran N., "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" in Journal of Inorganic Biochemistry, 211 (2020), https://doi.org/10.1016/j.jinorgbio.2020.111207 . .