Novel diphenyltin(IV) complexes with carboxylato N-functionalized 2-quinolone ligands: Synthesis, characterization and in vitro anticancer studies
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2024
Authors
Kasalović, Marijana P.Jelača, Sanja
Maksimović-Ivanić, Danijela
Lađarević, Jelena
Radovanović, Lidija
Božić, Bojan
Mijatović, Sanja
Pantelić, Nebojša Đ.
Kaluđerović, Goran N.
Article (Published version)
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Three new diphenyltin(IV) complexes, bis(3-(4-methyl-2-oxoquinolinyl-1(2H)-yl)propanoato)diphenyltin(IV)
(1), bis(2-(4-methyl-2-oxoquinolin-1(2H)-yl)ethanoato)diphenyltin(IV) (2), and bis(2-(4-hydroxy-2-oxoquinolin1(2H)-yl)ethanoato)diphenyltin(IV) (3), were synthesized and characterized by elemental microanalysis, FT-IR
spectroscopy, and multinuclear (
1
H, 13C and 119Sn) NMR spectroscopy. Crystal structure of ligand precursor,
2-(4-methyl-2-oxoquinolinyl-1-(2H)-yl)acetic acid (HL2), has been determined by X-ray diffraction studies.
Asymmetric bidentate coordination of the carboxylato ligands and skew trapezoidal structures are assumed for
the synthesized complexes. In vitro anticancer activity of the synthesized diphenyltin(IV) complexes was evaluated against three human: MCF-7 (breast adenocarcinoma), A375 (melanoma), HCT116 (colorectal carcinoma),
and three mouse tumor cell lines: 4T1 (breast carcinoma), B16 (melanoma), CT26 (colon carcinoma) using MTT
and CV assays. The I...C50 values fall in the range from 0.1 to 3.7 μM. Flow cytometric analysis and fluorescent
microscopy suggest that complex 1 induces caspase-dependent apoptosis followed with strong blockade of cell
division in HCT116 cells. Since complex 1 showed ROS/RNS scavenging potential mentioned cytotoxicity was
not connected with oxidative stress.
Keywords:
Diphenyltin(IV) / 2-quinolones, cytotoxicity / Apoptosis / ROS/RNS / Flow cytometrySource:
Journal of Inorganic Biochemistry, 2024, 250, 112399-Publisher:
- Elsevier Inc.
Funding / projects:
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200116 (University of Belgrade, Faculty of Agriculture) (RS-MESTD-inst-2020-200116)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200007 (University of Belgrade, Institute for Biological Research 'Siniša Stanković') (RS-MESTD-inst-2020-200007)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200135 (University of Belgrade, Faculty of Technology and Metallurgy) (RS-MESTD-inst-2020-200135)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200287 (Innovation Center of the Faculty of Technology and Metallurgy) (RS-MESTD-inst-2020-200287)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200178 (University of Belgrade, Faculty of Biology) (RS-MESTD-inst-2020-200178)
- German Academic Exchange Service DAAD (Project “International HoMe“57561680)
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Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Kasalović, Marijana P. AU - Jelača, Sanja AU - Maksimović-Ivanić, Danijela AU - Lađarević, Jelena AU - Radovanović, Lidija AU - Božić, Bojan AU - Mijatović, Sanja AU - Pantelić, Nebojša Đ. AU - Kaluđerović, Goran N. PY - 2024 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6760 AB - Three new diphenyltin(IV) complexes, bis(3-(4-methyl-2-oxoquinolinyl-1(2H)-yl)propanoato)diphenyltin(IV) (1), bis(2-(4-methyl-2-oxoquinolin-1(2H)-yl)ethanoato)diphenyltin(IV) (2), and bis(2-(4-hydroxy-2-oxoquinolin1(2H)-yl)ethanoato)diphenyltin(IV) (3), were synthesized and characterized by elemental microanalysis, FT-IR spectroscopy, and multinuclear ( 1 H, 13C and 119Sn) NMR spectroscopy. Crystal structure of ligand precursor, 2-(4-methyl-2-oxoquinolinyl-1-(2H)-yl)acetic acid (HL2), has been determined by X-ray diffraction studies. Asymmetric bidentate coordination of the carboxylato ligands and skew trapezoidal structures are assumed for the synthesized complexes. In vitro anticancer activity of the synthesized diphenyltin(IV) complexes was evaluated against three human: MCF-7 (breast adenocarcinoma), A375 (melanoma), HCT116 (colorectal carcinoma), and three mouse tumor cell lines: 4T1 (breast carcinoma), B16 (melanoma), CT26 (colon carcinoma) using MTT and CV assays. The IC50 values fall in the range from 0.1 to 3.7 μM. Flow cytometric analysis and fluorescent microscopy suggest that complex 1 induces caspase-dependent apoptosis followed with strong blockade of cell division in HCT116 cells. Since complex 1 showed ROS/RNS scavenging potential mentioned cytotoxicity was not connected with oxidative stress. PB - Elsevier Inc. T2 - Journal of Inorganic Biochemistry T1 - Novel diphenyltin(IV) complexes with carboxylato N-functionalized 2-quinolone ligands: Synthesis, characterization and in vitro anticancer studies SP - 112399 VL - 250 DO - 10.1016/j.jinorgbio.2023.112399 ER -
@article{ author = "Kasalović, Marijana P. and Jelača, Sanja and Maksimović-Ivanić, Danijela and Lađarević, Jelena and Radovanović, Lidija and Božić, Bojan and Mijatović, Sanja and Pantelić, Nebojša Đ. and Kaluđerović, Goran N.", year = "2024", abstract = "Three new diphenyltin(IV) complexes, bis(3-(4-methyl-2-oxoquinolinyl-1(2H)-yl)propanoato)diphenyltin(IV) (1), bis(2-(4-methyl-2-oxoquinolin-1(2H)-yl)ethanoato)diphenyltin(IV) (2), and bis(2-(4-hydroxy-2-oxoquinolin1(2H)-yl)ethanoato)diphenyltin(IV) (3), were synthesized and characterized by elemental microanalysis, FT-IR spectroscopy, and multinuclear ( 1 H, 13C and 119Sn) NMR spectroscopy. Crystal structure of ligand precursor, 2-(4-methyl-2-oxoquinolinyl-1-(2H)-yl)acetic acid (HL2), has been determined by X-ray diffraction studies. Asymmetric bidentate coordination of the carboxylato ligands and skew trapezoidal structures are assumed for the synthesized complexes. In vitro anticancer activity of the synthesized diphenyltin(IV) complexes was evaluated against three human: MCF-7 (breast adenocarcinoma), A375 (melanoma), HCT116 (colorectal carcinoma), and three mouse tumor cell lines: 4T1 (breast carcinoma), B16 (melanoma), CT26 (colon carcinoma) using MTT and CV assays. The IC50 values fall in the range from 0.1 to 3.7 μM. Flow cytometric analysis and fluorescent microscopy suggest that complex 1 induces caspase-dependent apoptosis followed with strong blockade of cell division in HCT116 cells. Since complex 1 showed ROS/RNS scavenging potential mentioned cytotoxicity was not connected with oxidative stress.", publisher = "Elsevier Inc.", journal = "Journal of Inorganic Biochemistry", title = "Novel diphenyltin(IV) complexes with carboxylato N-functionalized 2-quinolone ligands: Synthesis, characterization and in vitro anticancer studies", pages = "112399", volume = "250", doi = "10.1016/j.jinorgbio.2023.112399" }
Kasalović, M. P., Jelača, S., Maksimović-Ivanić, D., Lađarević, J., Radovanović, L., Božić, B., Mijatović, S., Pantelić, N. Đ.,& Kaluđerović, G. N.. (2024). Novel diphenyltin(IV) complexes with carboxylato N-functionalized 2-quinolone ligands: Synthesis, characterization and in vitro anticancer studies. in Journal of Inorganic Biochemistry Elsevier Inc.., 250, 112399. https://doi.org/10.1016/j.jinorgbio.2023.112399
Kasalović MP, Jelača S, Maksimović-Ivanić D, Lađarević J, Radovanović L, Božić B, Mijatović S, Pantelić NĐ, Kaluđerović GN. Novel diphenyltin(IV) complexes with carboxylato N-functionalized 2-quinolone ligands: Synthesis, characterization and in vitro anticancer studies. in Journal of Inorganic Biochemistry. 2024;250:112399. doi:10.1016/j.jinorgbio.2023.112399 .
Kasalović, Marijana P., Jelača, Sanja, Maksimović-Ivanić, Danijela, Lađarević, Jelena, Radovanović, Lidija, Božić, Bojan, Mijatović, Sanja, Pantelić, Nebojša Đ., Kaluđerović, Goran N., "Novel diphenyltin(IV) complexes with carboxylato N-functionalized 2-quinolone ligands: Synthesis, characterization and in vitro anticancer studies" in Journal of Inorganic Biochemistry, 250 (2024):112399, https://doi.org/10.1016/j.jinorgbio.2023.112399 . .