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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, Nebojša Đ.
Zmejkovski, Bojana
Božić, Bojan
Dojčinović, Biljana
Banjac, Nebojša R.
Wessjohann, Ludger A.
Kaluđerović, Goran N.
Article (Published version)
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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), 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 μM. Compound 1 exhibits the highest activity toward PC-3 cells (IC50 = 0.115 } 0.009 μM; 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, 212, 111207-
Publisher:
  • Elsevier
Funding / projects:
  • 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)
  • German Academic Exchange Service (DAAD) - grant number: 57448219
Note:
  • The peer-reviewed version: http://cer.ihtm.bg.ac.rs/handle/123456789/3654

DOI: 10.1016/j.jinorgbio.2020.111207

ISSN: 0162-0134

PubMed: 32801055

WoS: 000566344500012

Scopus: 2-s2.0-85089264363
[ Google Scholar ]
8
4
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/3653
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - 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/123456789/3653
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), 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 μM. Compound 1 exhibits the
highest activity toward PC-3 cells (IC50 = 0.115  } 0.009 μM; 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
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), 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 μM. Compound 1 exhibits the
highest activity toward PC-3 cells (IC50 = 0.115  } 0.009 μM; 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",
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 . .

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