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
Autori
Pantelić, Nebojša Đ.Zmejkovski, Bojana
Božić, Bojan
Dojčinović, Biljana
Banjac, Nebojša R.
Wessjohann, Ludger A.
Kaluđerović, Goran N.
Članak u časopisu (Recenzirana verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
Two novel triphenyltin(IV) compounds, [Ph3SnL1] (L1 = 2-(5-(4-fluorobenzylidene)-2,4-dioxotetrahydrothiazole-3-yl)propanoate (1)) and [Ph3SnL2] (L2 = 2-(5-(5-methyl-2-furfurylidene)-2,4-dioxotetrahydrothiazole-3-yl)propanoate (2)) were synthesized and characterized by FT-IR, (1H and 13C) 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), andHepG2 (hepatic) using MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-12 diphenyltetrazolium bromide) and CV (crystalviolet) assays. The IC50 values are found to be in the range from 0.11 to 0.50 μM. Compound 1 exhibits thehighest activity toward PC-3 cells (IC50 = 0.115 } 0.009 μM; CV assay). The tin and platinum uptake in PC-3cells showed a threefold lower uptake of tin in comparison to platinum (as cisplatin). Together with its higheractivity this indicates a much higher cell... inhibition potential of the tin compounds (calculated to ca. 50 to 100times). Morphological analysis suggested that the compounds induce apoptosis in PC-3 cells, and flow cytometryanalysis revealed that 1 and 2 induce autophagy as well as NO (nitric oxide) production.
Ključne reči:
Tin(IV) / In vitro / Prostate cancer / Apoptosis / Autophagy / NOIzvor:
Journal of Inorganic Biochemistry, 2020, 212, 111207-Izdavač:
- Elsevier
Finansiranje / projekti:
- Racionalni dizajn i sinteza biološki aktivnih i koordinacionih jedinjenja i funkcionalnih materijala, relevantnih u (bio)nanotehnologiji (RS-MESTD-Basic Research (BR or ON)-172035)
- Neuroendokrina kontrola sekrecije hormona rasta kod čoveka - novi izazovi. Kontrola energetske homeostaze kod čoveka u različitim patološkim stanjima. Kliničko-patološka korelacija i genetska osnova tumora hipofize i neuroendokrinih tumora (RS-MESTD-Basic Research (BR or ON)-175033)
- German Academic Exchange Service (DAAD) - grant number: 57448219
Napomena:
- This is the peer-reviewed version of the article: Nebojša Đ. Pantelić, Bojana B. Zmejkovski, Bojan Božić, Biljana Dojčinović, Nebojša R. Banjac, Ludger A. Wessjohann, Goran N. Kaluđerović, 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, Journal of Inorganic Biochemistry, 2020, 212, 111207, doi: https://doi.org/10.1016/j.jinorgbio.2020.111207
- The published version: http://cer.ihtm.bg.ac.rs/handle/123456789/3653
DOI: 10.1016/j.jinorgbio.2020.111207
ISSN: 0162-0134
PubMed: 32801055
WoS: 000566344500012
Scopus: 2-s2.0-85089264363
Institucija/grupa
IHTMTY - JOUR AU - Pantelić, Nebojša Đ. AU - Zmejkovski, Bojana AU - Božić, Bojan AU - Dojčinović, Biljana AU - Banjac, Nebojša R. AU - Wessjohann, Ludger A. AU - Kaluđerović, Goran N. PY - 2020 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3654 AB - Two novel triphenyltin(IV) compounds, [Ph3SnL1] (L1 = 2-(5-(4-fluorobenzylidene)-2,4-dioxotetrahydrothiazole-3-yl)propanoate (1)) and [Ph3SnL2] (L2 = 2-(5-(5-methyl-2-furfurylidene)-2,4-dioxotetrahydrothiazole-3-yl)propanoate (2)) were synthesized and characterized by FT-IR, (1H and 13C) 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), andHepG2 (hepatic) using MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-12 diphenyltetrazolium bromide) and CV (crystalviolet) assays. The IC50 values are found to be in the range from 0.11 to 0.50 μM. Compound 1 exhibits thehighest activity toward PC-3 cells (IC50 = 0.115 } 0.009 μM; CV assay). The tin and platinum uptake in PC-3cells showed a threefold lower uptake of tin in comparison to platinum (as cisplatin). Together with its higheractivity this indicates a much higher cell inhibition potential of the tin compounds (calculated to ca. 50 to 100times). Morphological analysis suggested that the compounds induce apoptosis in PC-3 cells, and flow cytometryanalysis revealed that 1 and 2 induce autophagy as well as NO (nitric oxide) production. PB - Elsevier 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 - 212 SP - 111207 DO - 10.1016/j.jinorgbio.2020.111207 ER -
@article{ author = "Pantelić, Nebojša Đ. and Zmejkovski, Bojana and Božić, Bojan and Dojčinović, Biljana and Banjac, Nebojša R. and Wessjohann, Ludger A. and Kaluđerović, Goran N.", year = "2020", abstract = "Two novel triphenyltin(IV) compounds, [Ph3SnL1] (L1 = 2-(5-(4-fluorobenzylidene)-2,4-dioxotetrahydrothiazole-3-yl)propanoate (1)) and [Ph3SnL2] (L2 = 2-(5-(5-methyl-2-furfurylidene)-2,4-dioxotetrahydrothiazole-3-yl)propanoate (2)) were synthesized and characterized by FT-IR, (1H and 13C) 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), andHepG2 (hepatic) using MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-12 diphenyltetrazolium bromide) and CV (crystalviolet) assays. The IC50 values are found to be in the range from 0.11 to 0.50 μM. Compound 1 exhibits thehighest activity toward PC-3 cells (IC50 = 0.115 } 0.009 μM; CV assay). The tin and platinum uptake in PC-3cells showed a threefold lower uptake of tin in comparison to platinum (as cisplatin). Together with its higheractivity this indicates a much higher cell inhibition potential of the tin compounds (calculated to ca. 50 to 100times). Morphological analysis suggested that the compounds induce apoptosis in PC-3 cells, and flow cytometryanalysis revealed that 1 and 2 induce autophagy as well as NO (nitric oxide) production.", publisher = "Elsevier", 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 = "212", pages = "111207", doi = "10.1016/j.jinorgbio.2020.111207" }
Pantelić, N. Đ., Zmejkovski, B., Božić, B., Dojčinović, B., Banjac, N. R., Wessjohann, L. A.,& Kaluđerović, 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., 212, 111207. https://doi.org/10.1016/j.jinorgbio.2020.111207
Pantelić NĐ, Zmejkovski B, Božić B, Dojčinović B, Banjac NR, Wessjohann LA, Kaluđerović 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;212:111207. doi:10.1016/j.jinorgbio.2020.111207 .
Pantelić, Nebojša Đ., Zmejkovski, Bojana, Božić, Bojan, Dojčinović, Biljana, Banjac, Nebojša R., Wessjohann, Ludger A., Kaluđerović, 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, 212 (2020):111207, https://doi.org/10.1016/j.jinorgbio.2020.111207 . .