TY  - JOUR
AU  - Tadić, Julijana D.
AU  - Lađarević, Jelena M.
AU  - Vitnik, Željko J.
AU  - Vitnik, Vesna D.
AU  - Stanojković, Tatjana P.
AU  - Matić, Ivana Z.
AU  - Mijin, Dušan Ž.
PY  - 2021
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/10890
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 μM) and PC-3 (48.98 μM) cancer cells, and normal MRC-5 (91.11 μM) 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
SP  - 109123
DO  - 10.1016/j.dyepig.2020.109123
ER  - 

@article{
author = "Tadić, Julijana D. and Lađarević, Jelena M. and Vitnik, Željko J. and Vitnik, Vesna D. and Stanojković, Tatjana P. and Matić, Ivana Z. and Mijin, Dušan Ž.",
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 μM) and PC-3 (48.98 μM) cancer cells, and normal MRC-5 (91.11 μM) 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",
pages = "109123",
doi = "10.1016/j.dyepig.2020.109123"
}

Tadić, J. D., Lađarević, J. M., Vitnik, Ž. J., Vitnik, V. D., Stanojković, T. P., Matić, I. Z.,& Mijin, D. Ž.. (2021). Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity. in Dyes and Pigments, 187, 109123.
https://doi.org/10.1016/j.dyepig.2020.109123

Tadić JD, Lađarević JM, Vitnik ŽJ, Vitnik VD, Stanojković TP, Matić IZ, Mijin DŽ. Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity. in Dyes and Pigments. 2021;187:109123.
doi:10.1016/j.dyepig.2020.109123 .

Tadić, Julijana D., Lađarević, Jelena M., Vitnik, Željko J., Vitnik, Vesna D., Stanojković, Tatjana P., Matić, Ivana Z., Mijin, Dušan Ž., "Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity" in Dyes and Pigments, 187 (2021):109123,
https://doi.org/10.1016/j.dyepig.2020.109123 . .

TY  - JOUR
AU  - Porobić, Slavica
AU  - Božić, Bojan Đ.
AU  - Dramićanin, Miroslav
AU  - Vitnik, Vesna
AU  - Vitnik, Željko J.
AU  - Marinović-Cincović, Milena
AU  - Mijin, Dušan Ž.
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8475
AB  - A series of nine 5-(4-substituted phenylazo)-3-amido-6-hydroxy-4-methyl-2-pyridones were synthesized and characterized by FT–IR, 1H and 13C NMR, UV–Vis, and PL spectroscopy. Photophysical properties of the dyes were examined in solvents of various polarities and at different pH values. The solvent effects on the absorbance and emission spectral shift were analyzed using Lippert–Mataga, Reichardt–Dimroth and Kamlet-Taft equations. Moreover, UV–Vis absorption and emission frequencies were correlated with Hammett substituent constants applying the linear free energy relationships. DFT calculations of the investigated dyes were accomplished to determine their structural and electronic properties. © 2019
T2  - Dyes and Pigments
T1  - Absorption and fluorescence spectral properties of azo dyes based on 3-amido-6-hydroxy-4-methyl-2-pyridone: Solvent and substituent effects
VL  - 175
SP  - 108139
DO  - 10.1016/j.dyepig.2019.108139
ER  - 

@article{
author = "Porobić, Slavica and Božić, Bojan Đ. and Dramićanin, Miroslav and Vitnik, Vesna and Vitnik, Željko J. and Marinović-Cincović, Milena and Mijin, Dušan Ž.",
year = "2020",
abstract = "A series of nine 5-(4-substituted phenylazo)-3-amido-6-hydroxy-4-methyl-2-pyridones were synthesized and characterized by FT–IR, 1H and 13C NMR, UV–Vis, and PL spectroscopy. Photophysical properties of the dyes were examined in solvents of various polarities and at different pH values. The solvent effects on the absorbance and emission spectral shift were analyzed using Lippert–Mataga, Reichardt–Dimroth and Kamlet-Taft equations. Moreover, UV–Vis absorption and emission frequencies were correlated with Hammett substituent constants applying the linear free energy relationships. DFT calculations of the investigated dyes were accomplished to determine their structural and electronic properties. © 2019",
journal = "Dyes and Pigments",
title = "Absorption and fluorescence spectral properties of azo dyes based on 3-amido-6-hydroxy-4-methyl-2-pyridone: Solvent and substituent effects",
volume = "175",
pages = "108139",
doi = "10.1016/j.dyepig.2019.108139"
}

Porobić, S., Božić, B. Đ., Dramićanin, M., Vitnik, V., Vitnik, Ž. J., Marinović-Cincović, M.,& Mijin, D. Ž.. (2020). Absorption and fluorescence spectral properties of azo dyes based on 3-amido-6-hydroxy-4-methyl-2-pyridone: Solvent and substituent effects. in Dyes and Pigments, 175, 108139.
https://doi.org/10.1016/j.dyepig.2019.108139

Porobić S, Božić BĐ, Dramićanin M, Vitnik V, Vitnik ŽJ, Marinović-Cincović M, Mijin DŽ. Absorption and fluorescence spectral properties of azo dyes based on 3-amido-6-hydroxy-4-methyl-2-pyridone: Solvent and substituent effects. in Dyes and Pigments. 2020;175:108139.
doi:10.1016/j.dyepig.2019.108139 .

Porobić, Slavica, Božić, Bojan Đ., Dramićanin, Miroslav, Vitnik, Vesna, Vitnik, Željko J., Marinović-Cincović, Milena, Mijin, Dušan Ž., "Absorption and fluorescence spectral properties of azo dyes based on 3-amido-6-hydroxy-4-methyl-2-pyridone: Solvent and substituent effects" in Dyes and Pigments, 175 (2020):108139,
https://doi.org/10.1016/j.dyepig.2019.108139 . .

TY  - JOUR
AU  - Miodragović Đenana U.
AU  - Mitić, Dragana M.
AU  - Miodragovic, Zoran M.
AU  - Bogdanović, Goran A.
AU  - Vitnik, Željko J.
AU  - Vitorovic, Maja D.
AU  - Radulovic, Milanka D.
AU  - Nastasijević, Branislav J.
AU  - Juranić, Ivan O.
AU  - Anđelković, Katarina
PY  - 2008
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/3363
AB  - For the first time, complexes of Zn(II), Cd(II) and Co(II) (1-3) with N-benzyloxycarbonylglycine have been synthesized and characterized. The complexes adopt tetrahedral, pentagonal-bipyramidal and octahedral geometry, respectively. The structure of the polymeric cadmium complex was resolved by single crystal X-ray analysis. The cadmium ion has a distorted pentagonal-bipyramidal coordination formed by two water molecules and two N-benzyloxycarbonylglycinato ligands (N-Boc) coordinated in different fashions, one as bidentate and the second connecting three cadmium atoms. In a rather complicated 2D supramolecular structure, the phenyl rings interact mutually exclusively by the CH center dot center dot center dot pi interactions. Investigation of the antimicrobial activity of the obtained complexes and N-benzyloxycarbonylglycine revealed that the ligand does not inhibit the growth of Candida albicans, whereas the newly synthesized complexes suppress the growth of this human fungal pathogen. (c) 2007 Elsevier B.V. All rights reserved.
T2  - Inorganica Chimica Acta
T1  - Syntheses, characterization and antimicrobial activity of the first complexes of Zn(II), Cd(II) and Co(II) with N-benzyloxycarbonylglycine - X-ray crystal structure of the polymeric Cd(II) complex
VL  - 361
IS  - 1
SP  - 86
EP  - 94
DO  - 10.1016/j.ica.2007.06.041
ER  - 

@article{
author = "Miodragović Đenana U. and Mitić, Dragana M. and Miodragovic, Zoran M. and Bogdanović, Goran A. and Vitnik, Željko J. and Vitorovic, Maja D. and Radulovic, Milanka D. and Nastasijević, Branislav J. and Juranić, Ivan O. and Anđelković, Katarina",
year = "2008",
abstract = "For the first time, complexes of Zn(II), Cd(II) and Co(II) (1-3) with N-benzyloxycarbonylglycine have been synthesized and characterized. The complexes adopt tetrahedral, pentagonal-bipyramidal and octahedral geometry, respectively. The structure of the polymeric cadmium complex was resolved by single crystal X-ray analysis. The cadmium ion has a distorted pentagonal-bipyramidal coordination formed by two water molecules and two N-benzyloxycarbonylglycinato ligands (N-Boc) coordinated in different fashions, one as bidentate and the second connecting three cadmium atoms. In a rather complicated 2D supramolecular structure, the phenyl rings interact mutually exclusively by the CH center dot center dot center dot pi interactions. Investigation of the antimicrobial activity of the obtained complexes and N-benzyloxycarbonylglycine revealed that the ligand does not inhibit the growth of Candida albicans, whereas the newly synthesized complexes suppress the growth of this human fungal pathogen. (c) 2007 Elsevier B.V. All rights reserved.",
journal = "Inorganica Chimica Acta",
title = "Syntheses, characterization and antimicrobial activity of the first complexes of Zn(II), Cd(II) and Co(II) with N-benzyloxycarbonylglycine - X-ray crystal structure of the polymeric Cd(II) complex",
volume = "361",
number = "1",
pages = "86-94",
doi = "10.1016/j.ica.2007.06.041"
}

Miodragović Đenana U., Mitić, D. M., Miodragovic, Z. M., Bogdanović, G. A., Vitnik, Ž. J., Vitorovic, M. D., Radulovic, M. D., Nastasijević, B. J., Juranić, I. O.,& Anđelković, K.. (2008). Syntheses, characterization and antimicrobial activity of the first complexes of Zn(II), Cd(II) and Co(II) with N-benzyloxycarbonylglycine - X-ray crystal structure of the polymeric Cd(II) complex. in Inorganica Chimica Acta, 361(1), 86-94.
https://doi.org/10.1016/j.ica.2007.06.041

Miodragović Đenana U., Mitić DM, Miodragovic ZM, Bogdanović GA, Vitnik ŽJ, Vitorovic MD, Radulovic MD, Nastasijević BJ, Juranić IO, Anđelković K. Syntheses, characterization and antimicrobial activity of the first complexes of Zn(II), Cd(II) and Co(II) with N-benzyloxycarbonylglycine - X-ray crystal structure of the polymeric Cd(II) complex. in Inorganica Chimica Acta. 2008;361(1):86-94.
doi:10.1016/j.ica.2007.06.041 .

Miodragović Đenana U., Mitić, Dragana M., Miodragovic, Zoran M., Bogdanović, Goran A., Vitnik, Željko J., Vitorovic, Maja D., Radulovic, Milanka D., Nastasijević, Branislav J., Juranić, Ivan O., Anđelković, Katarina, "Syntheses, characterization and antimicrobial activity of the first complexes of Zn(II), Cd(II) and Co(II) with N-benzyloxycarbonylglycine - X-ray crystal structure of the polymeric Cd(II) complex" in Inorganica Chimica Acta, 361, no. 1 (2008):86-94,
https://doi.org/10.1016/j.ica.2007.06.041 . .