Vitnik, Zeljko J.

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  • Vitnik, Zeljko J. (2)

Author's Bibliography

Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity

Tadić, Julijana; Lađarević, Jelena; Vitnik, Zeljko J.; Vitnik, Vesna D.; Stanojkovic, Tatjana P.; Matic, Ivana Z.; Mijin, Dušan

(2021)

TY  - JOUR
AU  - Tadić, Julijana
AU  - Lađarević, Jelena
AU  - Vitnik, Zeljko J.
AU  - Vitnik, Vesna D.
AU  - Stanojkovic, Tatjana P.
AU  - Matic, Ivana Z.
AU  - Mijin, Dušan
PY  - 2021
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4895
AB  - Seven novel azo dyes with 2-pyridone and dihydropyrimidinone moieties have been synthesized and thoroughly characterized. The azo-hydrazone tautomerism has been investigated by experimental and theoretical approaches. The optimizations of geometries have been performed with density functional theory (DFT). The vibrational and NMR spectra were calculated and correlated with experimental ones. Furthermore, quantum chemical descriptors were calculated and MEP maps were plotted to determine biological reactivity of dyes. The antioxidant assay evinced that 5, 6 and 7 are promising antioxidant candidates. In vitro cytotoxic activity was studied against three malignant cell lines: prostate adenocarcinoma (PC-3), lung carcinoma (A549) and chronic myelogenous leukemia (K562), as well as against human normal lung fibroblasts (MRC-5), using MTT assay. Examination of cytotoxic effects on human cancer cell lines showed the concentration dependent cytotoxicity of all investigated compounds. The K562 cells were the most sensitive to the cytotoxicity of the compounds 3, 5 and 6, wherein compound 5 was particularly prominent and selective in cytotoxic action between K562 (24.97 mu M) and PC-3 (48.98 mu M) cancer cells, and normal MRC-5 (91.11 mu M) cells. Moreover, the cell cycle analysis of compound 5 was examined in K562 cells, by flow cytometry, to study its mechanism of anticancer action. Finally, in silico evaluation of physicochemical parameters, druglikeness and ADME properties showed that investigated compounds are orally bioavailable with no permeation to the blood brain barrier.
T2  - Dyes and Pigments
T1  - Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity
VL  - 187
DO  - 10.1016/j.dyepig.2020.109123
ER  - 
@article{
author = "Tadić, Julijana and Lađarević, Jelena and Vitnik, Zeljko J. and Vitnik, Vesna D. and Stanojkovic, Tatjana P. and Matic, Ivana Z. and Mijin, Dušan",
year = "2021",
abstract = "Seven novel azo dyes with 2-pyridone and dihydropyrimidinone moieties have been synthesized and thoroughly characterized. The azo-hydrazone tautomerism has been investigated by experimental and theoretical approaches. The optimizations of geometries have been performed with density functional theory (DFT). The vibrational and NMR spectra were calculated and correlated with experimental ones. Furthermore, quantum chemical descriptors were calculated and MEP maps were plotted to determine biological reactivity of dyes. The antioxidant assay evinced that 5, 6 and 7 are promising antioxidant candidates. In vitro cytotoxic activity was studied against three malignant cell lines: prostate adenocarcinoma (PC-3), lung carcinoma (A549) and chronic myelogenous leukemia (K562), as well as against human normal lung fibroblasts (MRC-5), using MTT assay. Examination of cytotoxic effects on human cancer cell lines showed the concentration dependent cytotoxicity of all investigated compounds. The K562 cells were the most sensitive to the cytotoxicity of the compounds 3, 5 and 6, wherein compound 5 was particularly prominent and selective in cytotoxic action between K562 (24.97 mu M) and PC-3 (48.98 mu M) cancer cells, and normal MRC-5 (91.11 mu M) cells. Moreover, the cell cycle analysis of compound 5 was examined in K562 cells, by flow cytometry, to study its mechanism of anticancer action. Finally, in silico evaluation of physicochemical parameters, druglikeness and ADME properties showed that investigated compounds are orally bioavailable with no permeation to the blood brain barrier.",
journal = "Dyes and Pigments",
title = "Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity",
volume = "187",
doi = "10.1016/j.dyepig.2020.109123"
}
Tadić, J., Lađarević, J., Vitnik, Z. J., Vitnik, V. D., Stanojkovic, T. P., Matic, I. Z.,& Mijin, D.. (2021). Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity. in Dyes and Pigments, 187.
https://doi.org/10.1016/j.dyepig.2020.109123
Tadić J, Lađarević J, Vitnik ZJ, Vitnik VD, Stanojkovic TP, Matic IZ, Mijin D. Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity. in Dyes and Pigments. 2021;187.
doi:10.1016/j.dyepig.2020.109123 .
Tadić, Julijana, Lađarević, Jelena, Vitnik, Zeljko J., Vitnik, Vesna D., Stanojkovic, Tatjana P., Matic, Ivana Z., Mijin, Dušan, "Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity" in Dyes and Pigments, 187 (2021),
https://doi.org/10.1016/j.dyepig.2020.109123 . .
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Charge assisted assembly of zwitterionic pyridone hydrates

Mašulović, Aleksandra; Lađarević, Jelena; Radovanović, Lidija; Vitnik, Zeljko J.; Vitnik, Vesna D.; Rogan, Jelena; Mijin, Dušan

(2021)

TY  - JOUR
AU  - Mašulović, Aleksandra
AU  - Lađarević, Jelena
AU  - Radovanović, Lidija
AU  - Vitnik, Zeljko J.
AU  - Vitnik, Vesna D.
AU  - Rogan, Jelena
AU  - Mijin, Dušan
PY  - 2021
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4911
AB  - Two pyridone derivatives, bearing the pyridinium moiety (1), or dimethylpyridinium moiety (2), have been synthesized and their crystal structures have been determined. The compounds crystalize in hydrated zwitterionic forms with either two (1.2H(2)O) or four (2.4H(2)O) water molecules. The zwitteri-onic networks contain different types of water clusters, generated into channels, incorporating them into the network by sandwiching. The type of channel depends on the crystal lattice and the nature of non-covalent interactions established between zwitterions as well as the number of water molecules incorporated into the architecture. 1 affords tubes filled in with water channels formed by water tetramers, contrary to 2, which affords a layered network altering the zwitterionic layer and the layer formed by water tetramers and hexamers. A detailed study of intermolecular interactions of both crystal structures and a quantification of interaction energies has been performed using PIXEL lattice energy calculations, giving an insight to a quantitative evaluation of interactions through Coulombic, disperse, repulsion and polarization energies. The strongest pairwise, in both structures, is found to be a dipole-dipole interaction between oppositely charged heterocyclic rings. The differences in the crystal packings of these hydrates have been elucidated by the fingerplot analysis. The comparative studies between experimental and calculated (DFT) data of molecules 1.H2O and 2.4H(2)O for systems of different complexity are performed. Furthermore, correlations of experimental and calculated bond lengths and the simulation of compound solvation with the CPCM model are done.
T2  - Journal of Molecular Structure
T1  - Charge assisted assembly of zwitterionic pyridone hydrates
VL  - 1237
DO  - 10.1016/j.molstruc.2021.130419
ER  - 
@article{
author = "Mašulović, Aleksandra and Lađarević, Jelena and Radovanović, Lidija and Vitnik, Zeljko J. and Vitnik, Vesna D. and Rogan, Jelena and Mijin, Dušan",
year = "2021",
abstract = "Two pyridone derivatives, bearing the pyridinium moiety (1), or dimethylpyridinium moiety (2), have been synthesized and their crystal structures have been determined. The compounds crystalize in hydrated zwitterionic forms with either two (1.2H(2)O) or four (2.4H(2)O) water molecules. The zwitteri-onic networks contain different types of water clusters, generated into channels, incorporating them into the network by sandwiching. The type of channel depends on the crystal lattice and the nature of non-covalent interactions established between zwitterions as well as the number of water molecules incorporated into the architecture. 1 affords tubes filled in with water channels formed by water tetramers, contrary to 2, which affords a layered network altering the zwitterionic layer and the layer formed by water tetramers and hexamers. A detailed study of intermolecular interactions of both crystal structures and a quantification of interaction energies has been performed using PIXEL lattice energy calculations, giving an insight to a quantitative evaluation of interactions through Coulombic, disperse, repulsion and polarization energies. The strongest pairwise, in both structures, is found to be a dipole-dipole interaction between oppositely charged heterocyclic rings. The differences in the crystal packings of these hydrates have been elucidated by the fingerplot analysis. The comparative studies between experimental and calculated (DFT) data of molecules 1.H2O and 2.4H(2)O for systems of different complexity are performed. Furthermore, correlations of experimental and calculated bond lengths and the simulation of compound solvation with the CPCM model are done.",
journal = "Journal of Molecular Structure",
title = "Charge assisted assembly of zwitterionic pyridone hydrates",
volume = "1237",
doi = "10.1016/j.molstruc.2021.130419"
}
Mašulović, A., Lađarević, J., Radovanović, L., Vitnik, Z. J., Vitnik, V. D., Rogan, J.,& Mijin, D.. (2021). Charge assisted assembly of zwitterionic pyridone hydrates. in Journal of Molecular Structure, 1237.
https://doi.org/10.1016/j.molstruc.2021.130419
Mašulović A, Lađarević J, Radovanović L, Vitnik ZJ, Vitnik VD, Rogan J, Mijin D. Charge assisted assembly of zwitterionic pyridone hydrates. in Journal of Molecular Structure. 2021;1237.
doi:10.1016/j.molstruc.2021.130419 .
Mašulović, Aleksandra, Lađarević, Jelena, Radovanović, Lidija, Vitnik, Zeljko J., Vitnik, Vesna D., Rogan, Jelena, Mijin, Dušan, "Charge assisted assembly of zwitterionic pyridone hydrates" in Journal of Molecular Structure, 1237 (2021),
https://doi.org/10.1016/j.molstruc.2021.130419 . .
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