Araškov, Jovana B.

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  • Araškov, Jovana B. (3)

Author's Bibliography

Zn(II) complexes with pyridyl-based 1,3-selen/thiazolyl-hydrazones: A comparative study

Višnjevac, Aleksandar; Araškov, Jovana B.; Nikolić, Milan; Bojić-Trbojević, Žanka; Pirković, Andrea; Dekanski, Dragana; Mitić, Dragana; Blagojević, Vladimir; Filipović, Nenad R.; Todorović, Tamara R.

(2023)

TY  - JOUR
AU  - Višnjevac, Aleksandar
AU  - Araškov, Jovana B.
AU  - Nikolić, Milan
AU  - Bojić-Trbojević, Žanka
AU  - Pirković, Andrea
AU  - Dekanski, Dragana
AU  - Mitić, Dragana
AU  - Blagojević, Vladimir
AU  - Filipović, Nenad R.
AU  - Todorović, Tamara R.
PY  - 2023
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/6304
AB  - The Zn(II) complexes [Zn(HLSe2)2](NO3)2∙CH3OH (2-NO3-Se) and [Zn(HLSe3)2](NO3)2·DMF (3-NO3-Se) with selenazolyl-hydrazone ligands 4-(4-methoxyphenyl)-2-(2-(pyridin-2-ylmethylene)hydrazinyl)-1,3-selenazole (HLSe2) and 4-(4-methylphenyl)-2-(2-(pyridin-2-ylmethylene)hydrazinyl)-1,3-selenazole (HLSe3) have been synthesized and characterized using singe crystal X-ray diffraction analysis. Antiproliferative activities of 2-NO3-Se and 3-NO3-Se, the corresponding ligands and sulphur isosteres of the complexes and the ligands were determined on non-malignant HTR-8/SVneo extravillous trophoblast cell line and malignant JEG-3 and JAr choriocarcinoma cell lines. All Zn complexes exhibited cytotoxic effect, comparable to that of a reference metal-based drug, cisplatin. The antioxidant activity of all compounds was determined in three antioxidant assays: ORAC (Oxygen Radical Absorbance Capacity), ABTS [(2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt] and CERAC [Ce(IV)-based reducing capacity]. As a result of synergy between Zn(II) and selenazolyl-hydrazone ligands, the complexes 2-NO3-Se and 3-NO3-Se appeared to be more active than Trolox, which is not the case for their sulfur counterparts. In-silico calculations of ADME properties pointed that the compounds possess some of desirable Lipinski rule principles. Applied algorithms did not report the compounds as potential PAINS or covalent inhibitors, although due to high molecular weight none of the compounds represent a potential lead compound. Toxicity prediction of the compounds is performed using machine learning models. The complexation of the ligands most likely reduces their toxicity or reduces their negative metabolic effects. © 2023 Elsevier B.V.
T2  - Journal of Molecular Structure
T2  - Journal of Molecular Structure
T1  - Zn(II) complexes with pyridyl-based 1,3-selen/thiazolyl-hydrazones: A comparative study
VL  - 1281
DO  - 10.1016/j.molstruc.2023.135193
ER  - 
@article{
author = "Višnjevac, Aleksandar and Araškov, Jovana B. and Nikolić, Milan and Bojić-Trbojević, Žanka and Pirković, Andrea and Dekanski, Dragana and Mitić, Dragana and Blagojević, Vladimir and Filipović, Nenad R. and Todorović, Tamara R.",
year = "2023",
abstract = "The Zn(II) complexes [Zn(HLSe2)2](NO3)2∙CH3OH (2-NO3-Se) and [Zn(HLSe3)2](NO3)2·DMF (3-NO3-Se) with selenazolyl-hydrazone ligands 4-(4-methoxyphenyl)-2-(2-(pyridin-2-ylmethylene)hydrazinyl)-1,3-selenazole (HLSe2) and 4-(4-methylphenyl)-2-(2-(pyridin-2-ylmethylene)hydrazinyl)-1,3-selenazole (HLSe3) have been synthesized and characterized using singe crystal X-ray diffraction analysis. Antiproliferative activities of 2-NO3-Se and 3-NO3-Se, the corresponding ligands and sulphur isosteres of the complexes and the ligands were determined on non-malignant HTR-8/SVneo extravillous trophoblast cell line and malignant JEG-3 and JAr choriocarcinoma cell lines. All Zn complexes exhibited cytotoxic effect, comparable to that of a reference metal-based drug, cisplatin. The antioxidant activity of all compounds was determined in three antioxidant assays: ORAC (Oxygen Radical Absorbance Capacity), ABTS [(2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt] and CERAC [Ce(IV)-based reducing capacity]. As a result of synergy between Zn(II) and selenazolyl-hydrazone ligands, the complexes 2-NO3-Se and 3-NO3-Se appeared to be more active than Trolox, which is not the case for their sulfur counterparts. In-silico calculations of ADME properties pointed that the compounds possess some of desirable Lipinski rule principles. Applied algorithms did not report the compounds as potential PAINS or covalent inhibitors, although due to high molecular weight none of the compounds represent a potential lead compound. Toxicity prediction of the compounds is performed using machine learning models. The complexation of the ligands most likely reduces their toxicity or reduces their negative metabolic effects. © 2023 Elsevier B.V.",
journal = "Journal of Molecular Structure, Journal of Molecular Structure",
title = "Zn(II) complexes with pyridyl-based 1,3-selen/thiazolyl-hydrazones: A comparative study",
volume = "1281",
doi = "10.1016/j.molstruc.2023.135193"
}
Višnjevac, A., Araškov, J. B., Nikolić, M., Bojić-Trbojević, Ž., Pirković, A., Dekanski, D., Mitić, D., Blagojević, V., Filipović, N. R.,& Todorović, T. R.. (2023). Zn(II) complexes with pyridyl-based 1,3-selen/thiazolyl-hydrazones: A comparative study. in Journal of Molecular Structure, 1281.
https://doi.org/10.1016/j.molstruc.2023.135193
Višnjevac A, Araškov JB, Nikolić M, Bojić-Trbojević Ž, Pirković A, Dekanski D, Mitić D, Blagojević V, Filipović NR, Todorović TR. Zn(II) complexes with pyridyl-based 1,3-selen/thiazolyl-hydrazones: A comparative study. in Journal of Molecular Structure. 2023;1281.
doi:10.1016/j.molstruc.2023.135193 .
Višnjevac, Aleksandar, Araškov, Jovana B., Nikolić, Milan, Bojić-Trbojević, Žanka, Pirković, Andrea, Dekanski, Dragana, Mitić, Dragana, Blagojević, Vladimir, Filipović, Nenad R., Todorović, Tamara R., "Zn(II) complexes with pyridyl-based 1,3-selen/thiazolyl-hydrazones: A comparative study" in Journal of Molecular Structure, 1281 (2023),
https://doi.org/10.1016/j.molstruc.2023.135193 . .
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Zn(II) complexes with thiazolyl–hydrazones: structure, intermolecular interactions, photophysical properties, computational study and anticancer activity

Araškov, Jovana B.; Višnjevac, Aleksandar; Popović, Jasminka; Blagojević, Vladimir; Fernandes, Henrique S.; Sousa, Sérgio F.; Novaković, Irena; Padrón, José M.; Holló, Berta Barta; Monge, Miguel; Rodríguez-Castillo, María; López-de-Luzuriaga, José M.; Filipović, Nenad R.; Todorović, Tamara R.

(2022)

TY  - JOUR
AU  - Araškov, Jovana B.
AU  - Višnjevac, Aleksandar
AU  - Popović, Jasminka
AU  - Blagojević, Vladimir
AU  - Fernandes, Henrique S.
AU  - Sousa, Sérgio F.
AU  - Novaković, Irena
AU  - Padrón, José M.
AU  - Holló, Berta Barta
AU  - Monge, Miguel
AU  - Rodríguez-Castillo, María
AU  - López-de-Luzuriaga, José M.
AU  - Filipović, Nenad R.
AU  - Todorović, Tamara R.
PY  - 2022
UR  - https://pubs.rsc.org/en/content/articlelanding/2022/ce/d2ce00443g
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/6118
AB  - Earth-abundant, cheap and non-toxic zinc-based coordination compounds are drawing research attention as promising candidates for various applications, such as photoluminescent materials and anticancer agents. In this paper we report six zinc complexes (1–3-NO3 and 1–3-Cl) with pyridyl-based thiazolyl–hydrazone ligands, which differ in the nature of substituents at the ligands' periphery, anion type, and geometry around the metal ion. The complexes were characterized by single-crystal and powder X-ray diffraction analysis, as well as IR and NMR spectroscopy. The symmetrical complexes 2-Cl and 3-Cl, where zinc atoms are located at a two-fold axis, do not exhibit photophysical properties, unlike their asymmetrical analogs 2-NO3 and 3-NO3 with the same complex cation. Asymmetrical pentacoordinated 1-Cl and hexacoordinated 1-NO3 complexes exhibit photophysical properties. An admixture of allowed intra-ligand (1IL) and chloro (X)-to-ligand charge-transfer (1XLCT) electronic transitions is responsible for the fluorescence of the 1-Cl complex. The origin of the emission of the 1-NO3 complex is ascribed to an admixture of 3IL and ligand-to-ligand charge-transfer (3LLCT) forbidden electronic transitions, while for 3-NO3 most electronic excitations are of LLCT character. The thermal stability of the complexes is in accord with the strength of respective intermolecular interactions. The antiproliferative activity of the complexes was in the nanomolar range on some of the investigated cancer cell lines. Contrary to the increase of antiproliferative activity of the complexes in comparison to the free ligands in cancer cell lines, an acute toxicity determined in the brine shrimp assay follows the opposite trend. The overall results suggest that Zn(II) thiazoyl–hydrazone complexes have considerable potential as multifunctional materials.
T2  - CrystEngComm
T2  - CrystEngCommCrystEngComm
T1  - Zn(II) complexes with thiazolyl–hydrazones: structure, intermolecular interactions, photophysical properties, computational study and anticancer activity
DO  - 10.1039/D2CE00443G
ER  - 
@article{
author = "Araškov, Jovana B. and Višnjevac, Aleksandar and Popović, Jasminka and Blagojević, Vladimir and Fernandes, Henrique S. and Sousa, Sérgio F. and Novaković, Irena and Padrón, José M. and Holló, Berta Barta and Monge, Miguel and Rodríguez-Castillo, María and López-de-Luzuriaga, José M. and Filipović, Nenad R. and Todorović, Tamara R.",
year = "2022",
abstract = "Earth-abundant, cheap and non-toxic zinc-based coordination compounds are drawing research attention as promising candidates for various applications, such as photoluminescent materials and anticancer agents. In this paper we report six zinc complexes (1–3-NO3 and 1–3-Cl) with pyridyl-based thiazolyl–hydrazone ligands, which differ in the nature of substituents at the ligands' periphery, anion type, and geometry around the metal ion. The complexes were characterized by single-crystal and powder X-ray diffraction analysis, as well as IR and NMR spectroscopy. The symmetrical complexes 2-Cl and 3-Cl, where zinc atoms are located at a two-fold axis, do not exhibit photophysical properties, unlike their asymmetrical analogs 2-NO3 and 3-NO3 with the same complex cation. Asymmetrical pentacoordinated 1-Cl and hexacoordinated 1-NO3 complexes exhibit photophysical properties. An admixture of allowed intra-ligand (1IL) and chloro (X)-to-ligand charge-transfer (1XLCT) electronic transitions is responsible for the fluorescence of the 1-Cl complex. The origin of the emission of the 1-NO3 complex is ascribed to an admixture of 3IL and ligand-to-ligand charge-transfer (3LLCT) forbidden electronic transitions, while for 3-NO3 most electronic excitations are of LLCT character. The thermal stability of the complexes is in accord with the strength of respective intermolecular interactions. The antiproliferative activity of the complexes was in the nanomolar range on some of the investigated cancer cell lines. Contrary to the increase of antiproliferative activity of the complexes in comparison to the free ligands in cancer cell lines, an acute toxicity determined in the brine shrimp assay follows the opposite trend. The overall results suggest that Zn(II) thiazoyl–hydrazone complexes have considerable potential as multifunctional materials.",
journal = "CrystEngComm, CrystEngCommCrystEngComm",
title = "Zn(II) complexes with thiazolyl–hydrazones: structure, intermolecular interactions, photophysical properties, computational study and anticancer activity",
doi = "10.1039/D2CE00443G"
}
Araškov, J. B., Višnjevac, A., Popović, J., Blagojević, V., Fernandes, H. S., Sousa, S. F., Novaković, I., Padrón, J. M., Holló, B. B., Monge, M., Rodríguez-Castillo, M., López-de-Luzuriaga, J. M., Filipović, N. R.,& Todorović, T. R.. (2022). Zn(II) complexes with thiazolyl–hydrazones: structure, intermolecular interactions, photophysical properties, computational study and anticancer activity. in CrystEngComm.
https://doi.org/10.1039/D2CE00443G
Araškov JB, Višnjevac A, Popović J, Blagojević V, Fernandes HS, Sousa SF, Novaković I, Padrón JM, Holló BB, Monge M, Rodríguez-Castillo M, López-de-Luzuriaga JM, Filipović NR, Todorović TR. Zn(II) complexes with thiazolyl–hydrazones: structure, intermolecular interactions, photophysical properties, computational study and anticancer activity. in CrystEngComm. 2022;.
doi:10.1039/D2CE00443G .
Araškov, Jovana B., Višnjevac, Aleksandar, Popović, Jasminka, Blagojević, Vladimir, Fernandes, Henrique S., Sousa, Sérgio F., Novaković, Irena, Padrón, José M., Holló, Berta Barta, Monge, Miguel, Rodríguez-Castillo, María, López-de-Luzuriaga, José M., Filipović, Nenad R., Todorović, Tamara R., "Zn(II) complexes with thiazolyl–hydrazones: structure, intermolecular interactions, photophysical properties, computational study and anticancer activity" in CrystEngComm (2022),
https://doi.org/10.1039/D2CE00443G . .
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Structural, antioxidant, antiproliferative and in‒silico study of pyridine-based hydrazonyl‒selenazoles and their sulphur isosteres

Araškov, Jovana B.; Nikolić, Milan; Armaković, Stevan; Armaković, Sanja; Rodić, Marko; Vušnjevac, Aleksandar; Padrón, José M.; Todorović, Tamara R.; Filipović, Nenad R.

(Elsevier B.V., 2021)

TY  - JOUR
AU  - Araškov, Jovana B.
AU  - Nikolić, Milan
AU  - Armaković, Stevan
AU  - Armaković, Sanja
AU  - Rodić, Marko
AU  - Vušnjevac, Aleksandar
AU  - Padrón, José M.
AU  - Todorović, Tamara R.
AU  - Filipović, Nenad R.
PY  - 2021
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/5849
AB  - To evaluate the impact of chalcogen atom type, we performed a comparative study of antioxidant capacity and antiproliferative activity of a focused library of three pyridine-based hydrazonyl-1,3-selenazoles and their sulfur isosteres in five antioxidant assays and in six human solid tumor cell lines, respectively. In-silico calculations were further used to check pharmacokinetic profiles of investigated compounds such as drug-likeness parameters and interaction with water. Generally, selenium compounds appear to be more potent in comparison to sulfur isosteres in the performed essays.
PB  - Elsevier B.V.
T2  - Journal of Molecular Structure
T1  - Structural, antioxidant, antiproliferative and in‒silico study of pyridine-based hydrazonyl‒selenazoles and their sulphur isosteres
SP  - 130512
VL  - 1240
DO  - 10.1016/j.molstruc.2021.130512
ER  - 
@article{
author = "Araškov, Jovana B. and Nikolić, Milan and Armaković, Stevan and Armaković, Sanja and Rodić, Marko and Vušnjevac, Aleksandar and Padrón, José M. and Todorović, Tamara R. and Filipović, Nenad R.",
year = "2021",
abstract = "To evaluate the impact of chalcogen atom type, we performed a comparative study of antioxidant capacity and antiproliferative activity of a focused library of three pyridine-based hydrazonyl-1,3-selenazoles and their sulfur isosteres in five antioxidant assays and in six human solid tumor cell lines, respectively. In-silico calculations were further used to check pharmacokinetic profiles of investigated compounds such as drug-likeness parameters and interaction with water. Generally, selenium compounds appear to be more potent in comparison to sulfur isosteres in the performed essays.",
publisher = "Elsevier B.V.",
journal = "Journal of Molecular Structure",
title = "Structural, antioxidant, antiproliferative and in‒silico study of pyridine-based hydrazonyl‒selenazoles and their sulphur isosteres",
pages = "130512",
volume = "1240",
doi = "10.1016/j.molstruc.2021.130512"
}
Araškov, J. B., Nikolić, M., Armaković, S., Armaković, S., Rodić, M., Vušnjevac, A., Padrón, J. M., Todorović, T. R.,& Filipović, N. R.. (2021). Structural, antioxidant, antiproliferative and in‒silico study of pyridine-based hydrazonyl‒selenazoles and their sulphur isosteres. in Journal of Molecular Structure
Elsevier B.V.., 1240, 130512.
https://doi.org/10.1016/j.molstruc.2021.130512
Araškov JB, Nikolić M, Armaković S, Armaković S, Rodić M, Vušnjevac A, Padrón JM, Todorović TR, Filipović NR. Structural, antioxidant, antiproliferative and in‒silico study of pyridine-based hydrazonyl‒selenazoles and their sulphur isosteres. in Journal of Molecular Structure. 2021;1240:130512.
doi:10.1016/j.molstruc.2021.130512 .
Araškov, Jovana B., Nikolić, Milan, Armaković, Stevan, Armaković, Sanja, Rodić, Marko, Vušnjevac, Aleksandar, Padrón, José M., Todorović, Tamara R., Filipović, Nenad R., "Structural, antioxidant, antiproliferative and in‒silico study of pyridine-based hydrazonyl‒selenazoles and their sulphur isosteres" in Journal of Molecular Structure, 1240 (2021):130512,
https://doi.org/10.1016/j.molstruc.2021.130512 . .
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