Novaković, Irena

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orcid::0000-0001-9881-1204
  • Novaković, Irena (8)
Projects

Author's Bibliography

Study of the anticancer potential of Cd complexes of selenazoyl-hydrazones and their sulfur isosters

Marković, Sanja B.; Maciejewska, Natalia; Olszewski, Mateusz; Višnjevac, Aleksandar; Puerta, Adrián; Padrón, José M.; Novaković, Irena; Kojić, Snežana; Fernandes, Henrique S.; Sousa, Sérgio F.; Ramotowska, Sandra; Chylewska, Agnieszka; Makowski, Mariusz; Todorović, Tamara R.; Filipović, Nenad R.

(2022)

TY  - JOUR
AU  - Marković, Sanja B.
AU  - Maciejewska, Natalia
AU  - Olszewski, Mateusz
AU  - Višnjevac, Aleksandar
AU  - Puerta, Adrián
AU  - Padrón, José M.
AU  - Novaković, Irena
AU  - Kojić, Snežana
AU  - Fernandes, Henrique S.
AU  - Sousa, Sérgio F.
AU  - Ramotowska, Sandra
AU  - Chylewska, Agnieszka
AU  - Makowski, Mariusz
AU  - Todorović, Tamara R.
AU  - Filipović, Nenad R.
PY  - 2022
UR  - https://www.sciencedirect.com/science/article/pii/S0223523422003518
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/6098
AB  - The biological activity of Cd compounds has been investigated scarce since Cd has been recognized as a human carcinogen. However, the toxicity of cadmium is comparable to the toxicity of noble metals such as Pt and Pd. The paradigm of metal toxicity has been challenged suggesting that metal toxicity is not a constant property, yet it depends on many factors like the presence of appropriate ligands. Studies on anticancer activity of cadmium complexes showed that the complexation of various ligands resulted in complexes that showed better activities than approved drugs. In the present study, cadmium complexes with biologically potent thiazolyl/selenazoyl-hydrazone ligands have been prepared, and tested for their activity against different types of tumor cell models. The complexation of ligands with Cd(II) resulted in a synergistic effect. The antiproliferative activity study revealed that all complexes are more active compared to 5-fluorouracil and cisplatin. The mechanism of tumor cell growth inhibition reveal that selenium-based compounds induce cell death in T-47D (gland carcinoma) cells through apoptosis via caspase-3/7 activation. Additionally, their pro-apoptotic effect was stronger compared to etoposide and cisplatin. Nuclease activity, detected by gel electrophoresis, may be the possible mechanism of anticancer action of investigated complexes.
T2  - European Journal of Medicinal Chemistry
T2  - European Journal of Medicinal ChemistryEuropean Journal of Medicinal Chemistry
T1  - Study of the anticancer potential of Cd complexes of selenazoyl-hydrazones and their sulfur isosters
EP  - 
SP  - 114449
VL  - 238
DO  - 10.1016/j.ejmech.2022.114449
ER  - 
@article{
author = "Marković, Sanja B. and Maciejewska, Natalia and Olszewski, Mateusz and Višnjevac, Aleksandar and Puerta, Adrián and Padrón, José M. and Novaković, Irena and Kojić, Snežana and Fernandes, Henrique S. and Sousa, Sérgio F. and Ramotowska, Sandra and Chylewska, Agnieszka and Makowski, Mariusz and Todorović, Tamara R. and Filipović, Nenad R.",
year = "2022",
abstract = "The biological activity of Cd compounds has been investigated scarce since Cd has been recognized as a human carcinogen. However, the toxicity of cadmium is comparable to the toxicity of noble metals such as Pt and Pd. The paradigm of metal toxicity has been challenged suggesting that metal toxicity is not a constant property, yet it depends on many factors like the presence of appropriate ligands. Studies on anticancer activity of cadmium complexes showed that the complexation of various ligands resulted in complexes that showed better activities than approved drugs. In the present study, cadmium complexes with biologically potent thiazolyl/selenazoyl-hydrazone ligands have been prepared, and tested for their activity against different types of tumor cell models. The complexation of ligands with Cd(II) resulted in a synergistic effect. The antiproliferative activity study revealed that all complexes are more active compared to 5-fluorouracil and cisplatin. The mechanism of tumor cell growth inhibition reveal that selenium-based compounds induce cell death in T-47D (gland carcinoma) cells through apoptosis via caspase-3/7 activation. Additionally, their pro-apoptotic effect was stronger compared to etoposide and cisplatin. Nuclease activity, detected by gel electrophoresis, may be the possible mechanism of anticancer action of investigated complexes.",
journal = "European Journal of Medicinal Chemistry, European Journal of Medicinal ChemistryEuropean Journal of Medicinal Chemistry",
title = "Study of the anticancer potential of Cd complexes of selenazoyl-hydrazones and their sulfur isosters",
pages = "-114449",
volume = "238",
doi = "10.1016/j.ejmech.2022.114449"
}
Marković, S. B., Maciejewska, N., Olszewski, M., Višnjevac, A., Puerta, A., Padrón, J. M., Novaković, I., Kojić, S., Fernandes, H. S., Sousa, S. F., Ramotowska, S., Chylewska, A., Makowski, M., Todorović, T. R.,& Filipović, N. R.. (2022). Study of the anticancer potential of Cd complexes of selenazoyl-hydrazones and their sulfur isosters. in European Journal of Medicinal Chemistry, 238, 114449-.
https://doi.org/10.1016/j.ejmech.2022.114449
Marković SB, Maciejewska N, Olszewski M, Višnjevac A, Puerta A, Padrón JM, Novaković I, Kojić S, Fernandes HS, Sousa SF, Ramotowska S, Chylewska A, Makowski M, Todorović TR, Filipović NR. Study of the anticancer potential of Cd complexes of selenazoyl-hydrazones and their sulfur isosters. in European Journal of Medicinal Chemistry. 2022;238:114449-.
doi:10.1016/j.ejmech.2022.114449 .
Marković, Sanja B., Maciejewska, Natalia, Olszewski, Mateusz, Višnjevac, Aleksandar, Puerta, Adrián, Padrón, José M., Novaković, Irena, Kojić, Snežana, Fernandes, Henrique S., Sousa, Sérgio F., Ramotowska, Sandra, Chylewska, Agnieszka, Makowski, Mariusz, Todorović, Tamara R., Filipović, Nenad R., "Study of the anticancer potential of Cd complexes of selenazoyl-hydrazones and their sulfur isosters" in European Journal of Medicinal Chemistry, 238 (2022):114449-,
https://doi.org/10.1016/j.ejmech.2022.114449 . .
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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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Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment-Independent 3D QSAR Models

Božić, Aleksandra R.; Bjelogrlić, Snežana; Novaković, Irena; Filipović, Nenad; Petrović, Predrag M.; Marinković, Aleksandar D.; Todorović, Tamara R.; Cvijetić, Ilija N.

(Wiley-V C H Verlag Gmbh, Weinheim, 2018)

TY  - JOUR
AU  - Božić, Aleksandra R.
AU  - Bjelogrlić, Snežana
AU  - Novaković, Irena
AU  - Filipović, Nenad
AU  - Petrović, Predrag M.
AU  - Marinković, Aleksandar D.
AU  - Todorović, Tamara R.
AU  - Cvijetić, Ilija N.
PY  - 2018
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/4753
AB  - Due to the rise of microbial strains resistant to conventional therapies, there is an urgent need for finding the new antimicrobial chemotypes. Heterocyclic compounds such as thiocarbohydrazones (TCHs) are able to interact with many metalloenzymes essential for microbes, while sulfur atom increases lipophilicity which is generally positively correlated with potency. In this paper, we report antibacterial and antifungal activity of twenty-two TCHs toward eight bacterial and three fungal strains. Furthermore, three alignment independent 3D QSAR models based on descriptors derived from molecular interaction fields (MIFs) are developed in order to rationalize structure-activity relationships for activities of TCHs toward S. aureus, P. aeruginosa and C. albicans. Several structural fragments important for biological activity are recognized in each model, and structural modifications which could lead to increased potency are suggested. Designed structures will be synthesized accordingly and tested toward the same microbial strains in order to obtain more potent derivatives.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistryselect
T1  - Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment-Independent 3D QSAR Models
EP  - 2221
IS  - 7
SP  - 2215
VL  - 3
DO  - 10.1002/slct.201702691
ER  - 
@article{
author = "Božić, Aleksandra R. and Bjelogrlić, Snežana and Novaković, Irena and Filipović, Nenad and Petrović, Predrag M. and Marinković, Aleksandar D. and Todorović, Tamara R. and Cvijetić, Ilija N.",
year = "2018",
abstract = "Due to the rise of microbial strains resistant to conventional therapies, there is an urgent need for finding the new antimicrobial chemotypes. Heterocyclic compounds such as thiocarbohydrazones (TCHs) are able to interact with many metalloenzymes essential for microbes, while sulfur atom increases lipophilicity which is generally positively correlated with potency. In this paper, we report antibacterial and antifungal activity of twenty-two TCHs toward eight bacterial and three fungal strains. Furthermore, three alignment independent 3D QSAR models based on descriptors derived from molecular interaction fields (MIFs) are developed in order to rationalize structure-activity relationships for activities of TCHs toward S. aureus, P. aeruginosa and C. albicans. Several structural fragments important for biological activity are recognized in each model, and structural modifications which could lead to increased potency are suggested. Designed structures will be synthesized accordingly and tested toward the same microbial strains in order to obtain more potent derivatives.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistryselect",
title = "Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment-Independent 3D QSAR Models",
pages = "2221-2215",
number = "7",
volume = "3",
doi = "10.1002/slct.201702691"
}
Božić, A. R., Bjelogrlić, S., Novaković, I., Filipović, N., Petrović, P. M., Marinković, A. D., Todorović, T. R.,& Cvijetić, I. N.. (2018). Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment-Independent 3D QSAR Models. in Chemistryselect
Wiley-V C H Verlag Gmbh, Weinheim., 3(7), 2215-2221.
https://doi.org/10.1002/slct.201702691
Božić AR, Bjelogrlić S, Novaković I, Filipović N, Petrović PM, Marinković AD, Todorović TR, Cvijetić IN. Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment-Independent 3D QSAR Models. in Chemistryselect. 2018;3(7):2215-2221.
doi:10.1002/slct.201702691 .
Božić, Aleksandra R., Bjelogrlić, Snežana, Novaković, Irena, Filipović, Nenad, Petrović, Predrag M., Marinković, Aleksandar D., Todorović, Tamara R., Cvijetić, Ilija N., "Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment-Independent 3D QSAR Models" in Chemistryselect, 3, no. 7 (2018):2215-2221,
https://doi.org/10.1002/slct.201702691 . .
1
16
6
17

Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues

Filipović, Nenad; Elshaflu, Hana; Grubisić, Sonja; Jovanović, Ljiljana S.; Rodić, Marko; Novaković, Irena; Malesević, Aleksandar; Djordjević, Ivana S.; Li, Haidong; Sojić, Neso; Marinković, Aleksandar; Todorović, Tamara R.

(Royal Soc Chemistry, Cambridge, 2017)

TY  - JOUR
AU  - Filipović, Nenad
AU  - Elshaflu, Hana
AU  - Grubisić, Sonja
AU  - Jovanović, Ljiljana S.
AU  - Rodić, Marko
AU  - Novaković, Irena
AU  - Malesević, Aleksandar
AU  - Djordjević, Ivana S.
AU  - Li, Haidong
AU  - Sojić, Neso
AU  - Marinković, Aleksandar
AU  - Todorović, Tamara R.
PY  - 2017
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/4392
AB  - The first Co(III) complexes with (1,3-selenazol-2-yl)hydrazones as an unexplored class of ligands were prepared and characterized by NMR spectroscopy and X-ray diffraction analysis. The novel ligands act as NNN tridentate chelators forming octahedral Co(III) complexes. The impact of structural changes on ligands' periphery as well as that of isosteric replacement of sulphur with selenium on the electrochemical and electronic absorption features of complexes are explored. To support the experimental data, density functional theory (DFT) calculations were also conducted. Theoretical NMR chemical shifts, the relative energies and natural bond orbital (NBO) analysis are calculated within the DFT approach, while the singlet excited state energies and HOMO-LUMO energy gap were calculated with time-dependent density functional theory (TD-DFT). The electrophilic f(-) and nucleophilic f(+) Fukui functions are well adapted to find the electrophile and nucleophile centres in the molecules. Both (1,3-selenazol-2-yl)- and (1,3-thiazol-2-yl) hydrazone Co(III) complexes showed potent antimicrobial and antioxidant activity. A significant difference among them was a smaller cytotoxicity of selenium compounds.
PB  - Royal Soc Chemistry, Cambridge
T2  - Dalton Transactions
T1  - Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues
EP  - 2924
IS  - 9
SP  - 2910
VL  - 46
DO  - 10.1039/c6dt04785h
ER  - 
@article{
author = "Filipović, Nenad and Elshaflu, Hana and Grubisić, Sonja and Jovanović, Ljiljana S. and Rodić, Marko and Novaković, Irena and Malesević, Aleksandar and Djordjević, Ivana S. and Li, Haidong and Sojić, Neso and Marinković, Aleksandar and Todorović, Tamara R.",
year = "2017",
abstract = "The first Co(III) complexes with (1,3-selenazol-2-yl)hydrazones as an unexplored class of ligands were prepared and characterized by NMR spectroscopy and X-ray diffraction analysis. The novel ligands act as NNN tridentate chelators forming octahedral Co(III) complexes. The impact of structural changes on ligands' periphery as well as that of isosteric replacement of sulphur with selenium on the electrochemical and electronic absorption features of complexes are explored. To support the experimental data, density functional theory (DFT) calculations were also conducted. Theoretical NMR chemical shifts, the relative energies and natural bond orbital (NBO) analysis are calculated within the DFT approach, while the singlet excited state energies and HOMO-LUMO energy gap were calculated with time-dependent density functional theory (TD-DFT). The electrophilic f(-) and nucleophilic f(+) Fukui functions are well adapted to find the electrophile and nucleophile centres in the molecules. Both (1,3-selenazol-2-yl)- and (1,3-thiazol-2-yl) hydrazone Co(III) complexes showed potent antimicrobial and antioxidant activity. A significant difference among them was a smaller cytotoxicity of selenium compounds.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Dalton Transactions",
title = "Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues",
pages = "2924-2910",
number = "9",
volume = "46",
doi = "10.1039/c6dt04785h"
}
Filipović, N., Elshaflu, H., Grubisić, S., Jovanović, L. S., Rodić, M., Novaković, I., Malesević, A., Djordjević, I. S., Li, H., Sojić, N., Marinković, A.,& Todorović, T. R.. (2017). Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues. in Dalton Transactions
Royal Soc Chemistry, Cambridge., 46(9), 2910-2924.
https://doi.org/10.1039/c6dt04785h
Filipović N, Elshaflu H, Grubisić S, Jovanović LS, Rodić M, Novaković I, Malesević A, Djordjević IS, Li H, Sojić N, Marinković A, Todorović TR. Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues. in Dalton Transactions. 2017;46(9):2910-2924.
doi:10.1039/c6dt04785h .
Filipović, Nenad, Elshaflu, Hana, Grubisić, Sonja, Jovanović, Ljiljana S., Rodić, Marko, Novaković, Irena, Malesević, Aleksandar, Djordjević, Ivana S., Li, Haidong, Sojić, Neso, Marinković, Aleksandar, Todorović, Tamara R., "Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues" in Dalton Transactions, 46, no. 9 (2017):2910-2924,
https://doi.org/10.1039/c6dt04785h . .
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Synthesis, antioxidant and antimicrobial activity of carbohydrazones

Božić, Aleksandra R.; Filipović, Nenad; Novaković, Irena; Bjelogrlić, Snežana; Nikolić, Jasmina B.; Drmanić, Sasa Z.; Marinković, Aleksandar D.

(Srpsko hemijsko društvo, Beograd, 2017)

TY  - JOUR
AU  - Božić, Aleksandra R.
AU  - Filipović, Nenad
AU  - Novaković, Irena
AU  - Bjelogrlić, Snežana
AU  - Nikolić, Jasmina B.
AU  - Drmanić, Sasa Z.
AU  - Marinković, Aleksandar D.
PY  - 2017
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/4456
AB  - Fourteen mono- and bis-carbohydrazone ligands have been synthesized and characterized. Antioxidant activity of the substances was investigated together with possible (E)/(Z) isomerization, and explained on the most active antioxidant compound 4 in various dimethyl sulphoxide-water mixtures. The addition of water to the system was involved in the formation of hydrated molecules which was confirmed in NMR after the addition of D2O. The ligands were tested in vitro against Gram-positive and Gram-negative bacteria and fungi, and their activity was discussed in relation to the structure of investigated carbohydrazone.
PB  - Srpsko hemijsko društvo, Beograd
T2  - JOURNAL OF THE SERBIAN CHEMICAL SOCIETY
T1  - Synthesis, antioxidant and antimicrobial activity of carbohydrazones
EP  - 508
IS  - 5
SP  - 495
VL  - 82
DO  - 10.2298/JSC161220045B
ER  - 
@article{
author = "Božić, Aleksandra R. and Filipović, Nenad and Novaković, Irena and Bjelogrlić, Snežana and Nikolić, Jasmina B. and Drmanić, Sasa Z. and Marinković, Aleksandar D.",
year = "2017",
abstract = "Fourteen mono- and bis-carbohydrazone ligands have been synthesized and characterized. Antioxidant activity of the substances was investigated together with possible (E)/(Z) isomerization, and explained on the most active antioxidant compound 4 in various dimethyl sulphoxide-water mixtures. The addition of water to the system was involved in the formation of hydrated molecules which was confirmed in NMR after the addition of D2O. The ligands were tested in vitro against Gram-positive and Gram-negative bacteria and fungi, and their activity was discussed in relation to the structure of investigated carbohydrazone.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "JOURNAL OF THE SERBIAN CHEMICAL SOCIETY",
title = "Synthesis, antioxidant and antimicrobial activity of carbohydrazones",
pages = "508-495",
number = "5",
volume = "82",
doi = "10.2298/JSC161220045B"
}
Božić, A. R., Filipović, N., Novaković, I., Bjelogrlić, S., Nikolić, J. B., Drmanić, S. Z.,& Marinković, A. D.. (2017). Synthesis, antioxidant and antimicrobial activity of carbohydrazones. in JOURNAL OF THE SERBIAN CHEMICAL SOCIETY
Srpsko hemijsko društvo, Beograd., 82(5), 495-508.
https://doi.org/10.2298/JSC161220045B
Božić AR, Filipović N, Novaković I, Bjelogrlić S, Nikolić JB, Drmanić SZ, Marinković AD. Synthesis, antioxidant and antimicrobial activity of carbohydrazones. in JOURNAL OF THE SERBIAN CHEMICAL SOCIETY. 2017;82(5):495-508.
doi:10.2298/JSC161220045B .
Božić, Aleksandra R., Filipović, Nenad, Novaković, Irena, Bjelogrlić, Snežana, Nikolić, Jasmina B., Drmanić, Sasa Z., Marinković, Aleksandar D., "Synthesis, antioxidant and antimicrobial activity of carbohydrazones" in JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 82, no. 5 (2017):495-508,
https://doi.org/10.2298/JSC161220045B . .
17
10
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Quinoline based mono- and bis-(thio) carbohydrazones: synthesis, anticancer activity in 2D and 3D cancer and cancer stem cell models

Božić, Aleksandra; Marinković, Aleksandar; Bjelogrlić, Snežana; Todorović, Tamara R.; Cvijetić, Ilija N.; Novaković, Irena; Muller, Christian D.; Filipović, Nenad

(Royal Soc Chemistry, Cambridge, 2016)

TY  - JOUR
AU  - Božić, Aleksandra
AU  - Marinković, Aleksandar
AU  - Bjelogrlić, Snežana
AU  - Todorović, Tamara R.
AU  - Cvijetić, Ilija N.
AU  - Novaković, Irena
AU  - Muller, Christian D.
AU  - Filipović, Nenad
PY  - 2016
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/4065
AB  - A comparative study of antitumor activity of mono- and bis-quinoline based (thio) carbohydrazones was investigated by a series of tests on two human malignant cell lines: acute monocytic leukemia (THP-1) and pancreatic adenocarcinoma cancer stem cells (AsPC-1). Thiocarbohydrazones (TCHs) revealed superior pro-apoptotic activity over carbohydrazones (CHs) on both tested cell phenotypes, also displaying multi-target profile activities. Programmed cell death triggered by TCHs was partially caspase-dependent, mainly caspase-8 related. Activity against cancer stem cells (CSCs) was evaluated on 2D monolayers and 3D spheroidal models, where two out of three tested bis-TCHs successfully stimulated apoptosis accompanied by a reduction in size of treated spheres. Additionally, all bis-TCHs induced significant decrease in percentage of CD44-expressing AsPC-1 cells that indicate on their ability to induce reprogramming of CSC phenotype. Current results highly support further assessment of bis-TCHs in order to specify their specific targets in cancer cells and particularly in the CSCs subpopulation.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Quinoline based mono- and bis-(thio) carbohydrazones: synthesis, anticancer activity in 2D and 3D cancer and cancer stem cell models
EP  - 104781
IS  - 106
SP  - 104763
VL  - 6
DO  - 10.1039/c6ra23940d
ER  - 
@article{
author = "Božić, Aleksandra and Marinković, Aleksandar and Bjelogrlić, Snežana and Todorović, Tamara R. and Cvijetić, Ilija N. and Novaković, Irena and Muller, Christian D. and Filipović, Nenad",
year = "2016",
abstract = "A comparative study of antitumor activity of mono- and bis-quinoline based (thio) carbohydrazones was investigated by a series of tests on two human malignant cell lines: acute monocytic leukemia (THP-1) and pancreatic adenocarcinoma cancer stem cells (AsPC-1). Thiocarbohydrazones (TCHs) revealed superior pro-apoptotic activity over carbohydrazones (CHs) on both tested cell phenotypes, also displaying multi-target profile activities. Programmed cell death triggered by TCHs was partially caspase-dependent, mainly caspase-8 related. Activity against cancer stem cells (CSCs) was evaluated on 2D monolayers and 3D spheroidal models, where two out of three tested bis-TCHs successfully stimulated apoptosis accompanied by a reduction in size of treated spheres. Additionally, all bis-TCHs induced significant decrease in percentage of CD44-expressing AsPC-1 cells that indicate on their ability to induce reprogramming of CSC phenotype. Current results highly support further assessment of bis-TCHs in order to specify their specific targets in cancer cells and particularly in the CSCs subpopulation.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Quinoline based mono- and bis-(thio) carbohydrazones: synthesis, anticancer activity in 2D and 3D cancer and cancer stem cell models",
pages = "104781-104763",
number = "106",
volume = "6",
doi = "10.1039/c6ra23940d"
}
Božić, A., Marinković, A., Bjelogrlić, S., Todorović, T. R., Cvijetić, I. N., Novaković, I., Muller, C. D.,& Filipović, N.. (2016). Quinoline based mono- and bis-(thio) carbohydrazones: synthesis, anticancer activity in 2D and 3D cancer and cancer stem cell models. in RSC Advances
Royal Soc Chemistry, Cambridge., 6(106), 104763-104781.
https://doi.org/10.1039/c6ra23940d
Božić A, Marinković A, Bjelogrlić S, Todorović TR, Cvijetić IN, Novaković I, Muller CD, Filipović N. Quinoline based mono- and bis-(thio) carbohydrazones: synthesis, anticancer activity in 2D and 3D cancer and cancer stem cell models. in RSC Advances. 2016;6(106):104763-104781.
doi:10.1039/c6ra23940d .
Božić, Aleksandra, Marinković, Aleksandar, Bjelogrlić, Snežana, Todorović, Tamara R., Cvijetić, Ilija N., Novaković, Irena, Muller, Christian D., Filipović, Nenad, "Quinoline based mono- and bis-(thio) carbohydrazones: synthesis, anticancer activity in 2D and 3D cancer and cancer stem cell models" in RSC Advances, 6, no. 106 (2016):104763-104781,
https://doi.org/10.1039/c6ra23940d . .
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Copper(II) complexes of N-heteroaromatic hydrazones: Synthesis, X-ray structure, magnetic behavior, and antibacterial activity

Filipović, Nenad; Borrmann, Horst; Todorović, Tamara; Borna, Marija; Spasojević, Vojislav; Sladić, Dušan M.; Novaković, Irena; Andjelković, Katarina

(Elsevier Science Sa, Lausanne, 2009)

TY  - JOUR
AU  - Filipović, Nenad
AU  - Borrmann, Horst
AU  - Todorović, Tamara
AU  - Borna, Marija
AU  - Spasojević, Vojislav
AU  - Sladić, Dušan M.
AU  - Novaković, Irena
AU  - Andjelković, Katarina
PY  - 2009
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/1998
AB  - Three novel copper(II) complexes as condensation derivatives of 2-pyridinecarboxaldehyde, 2-acetylpyridine or 2-quinolinecarboxaldehyde with ethyl hydrazinoacetate hydrochloride were synthesized. X-ray crystal structures of all three complexes were determined. Crystallographic data indicate a common basis of the structures with some major differences. Both pyridine derivatives form complexes of the type [CuCl2L] with distorted square-planar geometry around copper(II), but show a decisive difference in the side chain orientation. The quinoline derivative forms a dimeric complex of type [Cu2Cl4L2] with distorted trigonal bipyramidal geometry around copper(II), but a rather short Cu center dot center dot center dot Cu contact, which is reflected in its magnetic properties. All three complexes showed antibacterial activity.
PB  - Elsevier Science Sa, Lausanne
T2  - Inorganica Chimica Acta
T1  - Copper(II) complexes of N-heteroaromatic hydrazones: Synthesis, X-ray structure, magnetic behavior, and antibacterial activity
EP  - 2000
IS  - 6
SP  - 1996
VL  - 362
DO  - 10.1016/j.ica.2008.09.019
ER  - 
@article{
author = "Filipović, Nenad and Borrmann, Horst and Todorović, Tamara and Borna, Marija and Spasojević, Vojislav and Sladić, Dušan M. and Novaković, Irena and Andjelković, Katarina",
year = "2009",
abstract = "Three novel copper(II) complexes as condensation derivatives of 2-pyridinecarboxaldehyde, 2-acetylpyridine or 2-quinolinecarboxaldehyde with ethyl hydrazinoacetate hydrochloride were synthesized. X-ray crystal structures of all three complexes were determined. Crystallographic data indicate a common basis of the structures with some major differences. Both pyridine derivatives form complexes of the type [CuCl2L] with distorted square-planar geometry around copper(II), but show a decisive difference in the side chain orientation. The quinoline derivative forms a dimeric complex of type [Cu2Cl4L2] with distorted trigonal bipyramidal geometry around copper(II), but a rather short Cu center dot center dot center dot Cu contact, which is reflected in its magnetic properties. All three complexes showed antibacterial activity.",
publisher = "Elsevier Science Sa, Lausanne",
journal = "Inorganica Chimica Acta",
title = "Copper(II) complexes of N-heteroaromatic hydrazones: Synthesis, X-ray structure, magnetic behavior, and antibacterial activity",
pages = "2000-1996",
number = "6",
volume = "362",
doi = "10.1016/j.ica.2008.09.019"
}
Filipović, N., Borrmann, H., Todorović, T., Borna, M., Spasojević, V., Sladić, D. M., Novaković, I.,& Andjelković, K.. (2009). Copper(II) complexes of N-heteroaromatic hydrazones: Synthesis, X-ray structure, magnetic behavior, and antibacterial activity. in Inorganica Chimica Acta
Elsevier Science Sa, Lausanne., 362(6), 1996-2000.
https://doi.org/10.1016/j.ica.2008.09.019
Filipović N, Borrmann H, Todorović T, Borna M, Spasojević V, Sladić DM, Novaković I, Andjelković K. Copper(II) complexes of N-heteroaromatic hydrazones: Synthesis, X-ray structure, magnetic behavior, and antibacterial activity. in Inorganica Chimica Acta. 2009;362(6):1996-2000.
doi:10.1016/j.ica.2008.09.019 .
Filipović, Nenad, Borrmann, Horst, Todorović, Tamara, Borna, Marija, Spasojević, Vojislav, Sladić, Dušan M., Novaković, Irena, Andjelković, Katarina, "Copper(II) complexes of N-heteroaromatic hydrazones: Synthesis, X-ray structure, magnetic behavior, and antibacterial activity" in Inorganica Chimica Acta, 362, no. 6 (2009):1996-2000,
https://doi.org/10.1016/j.ica.2008.09.019 . .
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44

Synthesis, characterization and biological activity evaluation of novel Pd(II) and Pt(II) complexes with heterocyclic hydrazone ligands

Filipović, Nenad; Todorović, Tamara; Sladić, Dušan M.; Novaković, Irena; Jeremić, D.A.; Andjelković, K.K.

(8th Conference of the Yugoslav Materials Research Society, 2007)

TY  - CONF
AU  - Filipović, Nenad
AU  - Todorović, Tamara
AU  - Sladić, Dušan M.
AU  - Novaković, Irena
AU  - Jeremić, D.A.
AU  - Andjelković, K.K.
PY  - 2007
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/1361
AB  - New complexes of Pt(II) with condensation derivatives of ethyl hydrazino acetate and either 2-acetylpyridine or 2-quinolinecarboxaldehyde, and of Pd(II) with the condensation derivative of ethyl hydrazinoacetate and 2-quinolinecarboxaldehyde were synthesized and characterized by elemental analysis, IR, H-1- and C-13-NMR spectroscopy, and molar conductivity measurements. The complexes have a square planar geometry, ligands binding as bidentates in the neutral form, and the remaining two coordination sites being occupied by chloride ions. Biological activity of new complexes, and of previously synthesized Pd(II), Cd(II), Co(III) and Zn(II) complexes with this ligand type was evaluated by the brine shrimp test. All the complexes showed a moderate activity.
PB  - 8th Conference of the Yugoslav Materials Research Society
C3  - Materials Science Forum
T1  - Synthesis, characterization and biological activity evaluation of novel Pd(II) and Pt(II) complexes with heterocyclic hydrazone ligands
EP  - 427
SP  - 423
VL  - 555
DO  - 10.4028/0-87849-441-3.423
ER  - 
@conference{
author = "Filipović, Nenad and Todorović, Tamara and Sladić, Dušan M. and Novaković, Irena and Jeremić, D.A. and Andjelković, K.K.",
year = "2007",
abstract = "New complexes of Pt(II) with condensation derivatives of ethyl hydrazino acetate and either 2-acetylpyridine or 2-quinolinecarboxaldehyde, and of Pd(II) with the condensation derivative of ethyl hydrazinoacetate and 2-quinolinecarboxaldehyde were synthesized and characterized by elemental analysis, IR, H-1- and C-13-NMR spectroscopy, and molar conductivity measurements. The complexes have a square planar geometry, ligands binding as bidentates in the neutral form, and the remaining two coordination sites being occupied by chloride ions. Biological activity of new complexes, and of previously synthesized Pd(II), Cd(II), Co(III) and Zn(II) complexes with this ligand type was evaluated by the brine shrimp test. All the complexes showed a moderate activity.",
publisher = "8th Conference of the Yugoslav Materials Research Society",
journal = "Materials Science Forum",
title = "Synthesis, characterization and biological activity evaluation of novel Pd(II) and Pt(II) complexes with heterocyclic hydrazone ligands",
pages = "427-423",
volume = "555",
doi = "10.4028/0-87849-441-3.423"
}
Filipović, N., Todorović, T., Sladić, D. M., Novaković, I., Jeremić, D.A.,& Andjelković, K.K.. (2007). Synthesis, characterization and biological activity evaluation of novel Pd(II) and Pt(II) complexes with heterocyclic hydrazone ligands. in Materials Science Forum
8th Conference of the Yugoslav Materials Research Society., 555, 423-427.
https://doi.org/10.4028/0-87849-441-3.423
Filipović N, Todorović T, Sladić DM, Novaković I, Jeremić D, Andjelković K. Synthesis, characterization and biological activity evaluation of novel Pd(II) and Pt(II) complexes with heterocyclic hydrazone ligands. in Materials Science Forum. 2007;555:423-427.
doi:10.4028/0-87849-441-3.423 .
Filipović, Nenad, Todorović, Tamara, Sladić, Dušan M., Novaković, Irena, Jeremić, D.A., Andjelković, K.K., "Synthesis, characterization and biological activity evaluation of novel Pd(II) and Pt(II) complexes with heterocyclic hydrazone ligands" in Materials Science Forum, 555 (2007):423-427,
https://doi.org/10.4028/0-87849-441-3.423 . .
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