Triphenyltin(IV) compounds bearing modulated azo-carboxylato ligands: Synthesis, structural characterization, in vitro cytotoxicity, BSA/DNA binding affinity, and in silico studies
Само за регистроване кориснике
2024
Аутори
Pantelić, Nebojša Đ.Dimić, Dušan
Saoud, Mohamad
Matović, Luka R.
Jovanović Stević, Snežana
Kasalović, Marijana P.
Dojčinović, Biljana
Zmejkovski, Bojana B.
Banjac, Nebojša R.
Kaluđerović, Goran N.
Чланак у часопису (Објављена верзија)
,
© 2024 The Authors. Published by Elsevier B.V.
Метаподаци
Приказ свих података о документуАпстракт
Three novel triphenyltin(IV) compounds with modulated azo-carboxylato ligands: triphenylstannyl (E)-4-((2-hydroxynaphthalen-1-yl)diazenyl)benzoate, 1, triphenylstannyl (E)-4-((4-hydroxyphenyl)diazenyl)benzoate, 2, and triphenylstannyl (E)-4-((4-(dimethylamino)phenyl)diazenyl)benzoate, 3, were synthesized and characterized by elemental analysis, FTIR and NMR (1H, 13C, 119Sn) spectroscopy. The structures and spectra of compounds were predicted by Density Functional Theory (DFT) methods at B3LYP-D3BJ/6–311++G(d,p)(H,C,N,O)/LanL2DZ(Sn) level of theory. Furthermore, the antitumor potential of ligand precursors, HL1–HL3, and appropriate organotin(IV) compounds 1–3 was evaluated across mouse melanoma B16F1, human breast adenocarcinoma MCF-7, human colorectal HT-29 and human prostate PC3 cell lines using MTT and CV assays. The organotin(IV) compounds exhibit enhanced cellular uptake and efficacy in reducing viable cell numbers when compared to free acids. Specifically, compound 3 demonstrates ...a notable impact at lower nanomolar concentrations on all tested cell lines. Moreover, 3 induces cell death in MCF-7 cells by inhibiting cell division and promoting the overproduction of cellular nitric oxide (NO), ultimately leading to caspase-independent apoptosis. Importantly, this process occurs without concurrent activation of autophagy or the generation of ROS/RNS species. The binding affinity of 1–3 with calf thymus DNA (CT-DNA) and bovine serum albumin (BSA) was investigated by fluorescence spectroscopy and molecular docking simulations, suggesting their capacity to interact with these biomolecules.
Кључне речи:
Breast cancer / Cytotoxicity / DFT / DNA/BSA interactions / Flow cytometry / Triphenyltin(IV)Извор:
Journal of Organometallic Chemistry, 06-2024, 1013, 123158-Издавач:
- Elsevier B.V.
Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200116 (Универзитет у Београду, Пољопривредни факултет) (RS-MESTD-inst-2020-200116)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200146 (Универзитет у Београду, Факултет за физичку хемију) (RS-MESTD-inst-2020-200146)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200287 (Иновациони центар Технолошко-металуршког факултета у Београду доо) (RS-MESTD-inst-2020-200287)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200026 (Универзитет у Београду, Институт за хемију, технологију и металургију - ИХТМ) (RS-MESTD-inst-2020-200026)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200111 (Универзитет у Крагујевцу, Медицински факултет) (RS-MESTD-inst-2020-200111)
- German Academic Exchange Service DAAD PPP (Project number: 57656312)
Институција/група
Inovacioni centarTY - JOUR AU - Pantelić, Nebojša Đ. AU - Dimić, Dušan AU - Saoud, Mohamad AU - Matović, Luka R. AU - Jovanović Stević, Snežana AU - Kasalović, Marijana P. AU - Dojčinović, Biljana AU - Zmejkovski, Bojana B. AU - Banjac, Nebojša R. AU - Kaluđerović, Goran N. PY - 2024-06 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/7473 AB - Three novel triphenyltin(IV) compounds with modulated azo-carboxylato ligands: triphenylstannyl (E)-4-((2-hydroxynaphthalen-1-yl)diazenyl)benzoate, 1, triphenylstannyl (E)-4-((4-hydroxyphenyl)diazenyl)benzoate, 2, and triphenylstannyl (E)-4-((4-(dimethylamino)phenyl)diazenyl)benzoate, 3, were synthesized and characterized by elemental analysis, FTIR and NMR (1H, 13C, 119Sn) spectroscopy. The structures and spectra of compounds were predicted by Density Functional Theory (DFT) methods at B3LYP-D3BJ/6–311++G(d,p)(H,C,N,O)/LanL2DZ(Sn) level of theory. Furthermore, the antitumor potential of ligand precursors, HL1–HL3, and appropriate organotin(IV) compounds 1–3 was evaluated across mouse melanoma B16F1, human breast adenocarcinoma MCF-7, human colorectal HT-29 and human prostate PC3 cell lines using MTT and CV assays. The organotin(IV) compounds exhibit enhanced cellular uptake and efficacy in reducing viable cell numbers when compared to free acids. Specifically, compound 3 demonstrates a notable impact at lower nanomolar concentrations on all tested cell lines. Moreover, 3 induces cell death in MCF-7 cells by inhibiting cell division and promoting the overproduction of cellular nitric oxide (NO), ultimately leading to caspase-independent apoptosis. Importantly, this process occurs without concurrent activation of autophagy or the generation of ROS/RNS species. The binding affinity of 1–3 with calf thymus DNA (CT-DNA) and bovine serum albumin (BSA) was investigated by fluorescence spectroscopy and molecular docking simulations, suggesting their capacity to interact with these biomolecules. PB - Elsevier B.V. T2 - Journal of Organometallic Chemistry T1 - Triphenyltin(IV) compounds bearing modulated azo-carboxylato ligands: Synthesis, structural characterization, in vitro cytotoxicity, BSA/DNA binding affinity, and in silico studies SP - 123158 VL - 1013 DO - 10.1016/j.jorganchem.2024.123158 ER -
@article{ author = "Pantelić, Nebojša Đ. and Dimić, Dušan and Saoud, Mohamad and Matović, Luka R. and Jovanović Stević, Snežana and Kasalović, Marijana P. and Dojčinović, Biljana and Zmejkovski, Bojana B. and Banjac, Nebojša R. and Kaluđerović, Goran N.", year = "2024-06", abstract = "Three novel triphenyltin(IV) compounds with modulated azo-carboxylato ligands: triphenylstannyl (E)-4-((2-hydroxynaphthalen-1-yl)diazenyl)benzoate, 1, triphenylstannyl (E)-4-((4-hydroxyphenyl)diazenyl)benzoate, 2, and triphenylstannyl (E)-4-((4-(dimethylamino)phenyl)diazenyl)benzoate, 3, were synthesized and characterized by elemental analysis, FTIR and NMR (1H, 13C, 119Sn) spectroscopy. The structures and spectra of compounds were predicted by Density Functional Theory (DFT) methods at B3LYP-D3BJ/6–311++G(d,p)(H,C,N,O)/LanL2DZ(Sn) level of theory. Furthermore, the antitumor potential of ligand precursors, HL1–HL3, and appropriate organotin(IV) compounds 1–3 was evaluated across mouse melanoma B16F1, human breast adenocarcinoma MCF-7, human colorectal HT-29 and human prostate PC3 cell lines using MTT and CV assays. The organotin(IV) compounds exhibit enhanced cellular uptake and efficacy in reducing viable cell numbers when compared to free acids. Specifically, compound 3 demonstrates a notable impact at lower nanomolar concentrations on all tested cell lines. Moreover, 3 induces cell death in MCF-7 cells by inhibiting cell division and promoting the overproduction of cellular nitric oxide (NO), ultimately leading to caspase-independent apoptosis. Importantly, this process occurs without concurrent activation of autophagy or the generation of ROS/RNS species. The binding affinity of 1–3 with calf thymus DNA (CT-DNA) and bovine serum albumin (BSA) was investigated by fluorescence spectroscopy and molecular docking simulations, suggesting their capacity to interact with these biomolecules.", publisher = "Elsevier B.V.", journal = "Journal of Organometallic Chemistry", title = "Triphenyltin(IV) compounds bearing modulated azo-carboxylato ligands: Synthesis, structural characterization, in vitro cytotoxicity, BSA/DNA binding affinity, and in silico studies", pages = "123158", volume = "1013", doi = "10.1016/j.jorganchem.2024.123158" }
Pantelić, N. Đ., Dimić, D., Saoud, M., Matović, L. R., Jovanović Stević, S., Kasalović, M. P., Dojčinović, B., Zmejkovski, B. B., Banjac, N. R.,& Kaluđerović, G. N.. (2024-06). Triphenyltin(IV) compounds bearing modulated azo-carboxylato ligands: Synthesis, structural characterization, in vitro cytotoxicity, BSA/DNA binding affinity, and in silico studies. in Journal of Organometallic Chemistry Elsevier B.V.., 1013, 123158. https://doi.org/10.1016/j.jorganchem.2024.123158
Pantelić NĐ, Dimić D, Saoud M, Matović LR, Jovanović Stević S, Kasalović MP, Dojčinović B, Zmejkovski BB, Banjac NR, Kaluđerović GN. Triphenyltin(IV) compounds bearing modulated azo-carboxylato ligands: Synthesis, structural characterization, in vitro cytotoxicity, BSA/DNA binding affinity, and in silico studies. in Journal of Organometallic Chemistry. 2024;1013:123158. doi:10.1016/j.jorganchem.2024.123158 .
Pantelić, Nebojša Đ., Dimić, Dušan, Saoud, Mohamad, Matović, Luka R., Jovanović Stević, Snežana, Kasalović, Marijana P., Dojčinović, Biljana, Zmejkovski, Bojana B., Banjac, Nebojša R., Kaluđerović, Goran N., "Triphenyltin(IV) compounds bearing modulated azo-carboxylato ligands: Synthesis, structural characterization, in vitro cytotoxicity, BSA/DNA binding affinity, and in silico studies" in Journal of Organometallic Chemistry, 1013 (2024-06):123158, https://doi.org/10.1016/j.jorganchem.2024.123158 . .