Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids

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Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids (en)
Интеракције природних производа, њихових деривата и комплексних једињења са протеинима и нуклеинским киселинама (sr)
Interakcije prirodnih proizvoda, njihovih derivata i kompleksnih jedinjenja sa proteinima i nukleinskim kiselinama (sr_RS)
Authors

Publications

A detailed experimental and computational study of monocarbohydrazones

Božić, Aleksandra R.; Filipović, Nenad R.; Verbić, Tatjana; Milčić, Miloš; Todorović, Tamara; Cvijetić, Ilija; Klisurić, Olivera; Radišić, Marina; Marinković, Aleksandar

(Elsevier, Amsterdam, 2020)

TY  - JOUR
AU  - Božić, Aleksandra R.
AU  - Filipović, Nenad R.
AU  - Verbić, Tatjana
AU  - Milčić, Miloš
AU  - Todorović, Tamara
AU  - Cvijetić, Ilija
AU  - Klisurić, Olivera
AU  - Radišić, Marina
AU  - Marinković, Aleksandar
PY  - 2020
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4355
AB  - The substituent and solvent effect on intramolecular charge transfer (ICT) of twelve monocarbohydrazones (mCHs) were studied using experimental and theoretical methodology. The effects of specific and non-specific solvent-solute interactions on the UV-Vis absorption maxima shifts were evaluated using linear free energy relationships (LFERs) principles, i.e. using the Kamlet-Taft and Catalan models. Linear free energy relationships in the form of single substituent parameter equation (SSP) was used to analyze substituent effect on UV-Vis, NMR and pK(a) change. According to crystallographic data and quantum chemical calculations, the trans (E) form was found to be more stable. A photochromism of compounds with 2-hydroxyphenyl and 2-pyridylimino groups substituted at imine carbon atom results in E/Z isomerization due to creation of intermolecular hydrogen bond in E and Z form, respectively. Multiple stage mass spectrometry (MS-MSn) analysis was applied to define main fragmentation pathways. Furthermore, the experimental findings were interpreted with the aid of ab initio MP2/6-311 G(d,p) and time-dependent density functional (TD-DFT) methods. TD-DFT calculations were performed to quantify the efficiency of intramolecular charge transfer (ICT) with the aid of the charge-transfer distance (DCT) and the amount of transferred charge (QCT) calculation. It was found that both substituents and solvents influence electron density shift i.e. extent of conjugation, and affect ICT character in the course of excitation.
PB  - Elsevier, Amsterdam
T2  - Arabian Journal of Chemistry
T1  - A detailed experimental and computational study of monocarbohydrazones
EP  - 953
IS  - 1
SP  - 932
VL  - 13
DO  - 10.1016/j.arabjc.2017.08.010
ER  - 
@article{
author = "Božić, Aleksandra R. and Filipović, Nenad R. and Verbić, Tatjana and Milčić, Miloš and Todorović, Tamara and Cvijetić, Ilija and Klisurić, Olivera and Radišić, Marina and Marinković, Aleksandar",
year = "2020",
abstract = "The substituent and solvent effect on intramolecular charge transfer (ICT) of twelve monocarbohydrazones (mCHs) were studied using experimental and theoretical methodology. The effects of specific and non-specific solvent-solute interactions on the UV-Vis absorption maxima shifts were evaluated using linear free energy relationships (LFERs) principles, i.e. using the Kamlet-Taft and Catalan models. Linear free energy relationships in the form of single substituent parameter equation (SSP) was used to analyze substituent effect on UV-Vis, NMR and pK(a) change. According to crystallographic data and quantum chemical calculations, the trans (E) form was found to be more stable. A photochromism of compounds with 2-hydroxyphenyl and 2-pyridylimino groups substituted at imine carbon atom results in E/Z isomerization due to creation of intermolecular hydrogen bond in E and Z form, respectively. Multiple stage mass spectrometry (MS-MSn) analysis was applied to define main fragmentation pathways. Furthermore, the experimental findings were interpreted with the aid of ab initio MP2/6-311 G(d,p) and time-dependent density functional (TD-DFT) methods. TD-DFT calculations were performed to quantify the efficiency of intramolecular charge transfer (ICT) with the aid of the charge-transfer distance (DCT) and the amount of transferred charge (QCT) calculation. It was found that both substituents and solvents influence electron density shift i.e. extent of conjugation, and affect ICT character in the course of excitation.",
publisher = "Elsevier, Amsterdam",
journal = "Arabian Journal of Chemistry",
title = "A detailed experimental and computational study of monocarbohydrazones",
pages = "953-932",
number = "1",
volume = "13",
doi = "10.1016/j.arabjc.2017.08.010"
}
Božić, A. R., Filipović, N. R., Verbić, T., Milčić, M., Todorović, T., Cvijetić, I., Klisurić, O., Radišić, M.,& Marinković, A.. (2020). A detailed experimental and computational study of monocarbohydrazones. in Arabian Journal of Chemistry
Elsevier, Amsterdam., 13(1), 932-953.
https://doi.org/10.1016/j.arabjc.2017.08.010
Božić AR, Filipović NR, Verbić T, Milčić M, Todorović T, Cvijetić I, Klisurić O, Radišić M, Marinković A. A detailed experimental and computational study of monocarbohydrazones. in Arabian Journal of Chemistry. 2020;13(1):932-953.
doi:10.1016/j.arabjc.2017.08.010 .
Božić, Aleksandra R., Filipović, Nenad R., Verbić, Tatjana, Milčić, Miloš, Todorović, Tamara, Cvijetić, Ilija, Klisurić, Olivera, Radišić, Marina, Marinković, Aleksandar, "A detailed experimental and computational study of monocarbohydrazones" in Arabian Journal of Chemistry, 13, no. 1 (2020):932-953,
https://doi.org/10.1016/j.arabjc.2017.08.010 . .
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Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study

Assaleh, Mohamed H.; Božić, Aleksandra R.; Bjelogrlić, Snežana K.; Milošević, Milena D.; Simić, Milena R.; Marinković, Aleksandar; Cvijetić, Ilija

(Springer/Plenum Publishers, New York, 2019)

TY  - JOUR
AU  - Assaleh, Mohamed H.
AU  - Božić, Aleksandra R.
AU  - Bjelogrlić, Snežana K.
AU  - Milošević, Milena D.
AU  - Simić, Milena R.
AU  - Marinković, Aleksandar
AU  - Cvijetić, Ilija
PY  - 2019
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4147
AB  - Thiocarbohydrazones (TCHs) and structurally related molecules are versatile organic compounds which exert antioxidant, anticancer, and other beneficial health effects. The combination of UV/Vis, NMR spectroscopy, and quantum chemical calculations was used to rationalize the experimentally observed increase in the radical scavenging activity upon the addition of water in DMSO solution of TCHs. Mono- and bis(salicylaldehyde) TCHs (compounds 1 and 2) undergo water-induced E-to-Z isomerization which is followed by disruption of intramolecular hydrogen bond, ground state destabilization, and 11 kcal/mol decrease in the bond dissociation enthalpy (BDE). Electron spin delocalization is more pronounced in Z-isomers of 1 and 2. On the other hand, 2-acetylpyridine TCHs (compounds 3 and 4) undergo thione-to-thiol tautomerism which also decreases the BDE and facilitates the hydrogen atom transfer to 2,2-diphenyl-1-picrylhydrazyl radical (DPPH.). The appearance of thiolic -SH group as another reactive site toward free radicals improves the antioxidant activity of 3 and 4. The spin density of 3- and 4-thiol radicals is delocalized over the entire thiocarbohydrazide moiety compared to more localized spin of thione radicals. Additional stabilization of thiol radicals corroborates with the increased antioxidant activity. This study provides the new insights on the solution structure of TCHs, and also highlights the importance of solution structure determination when studying the structure-antioxidant relationships of isomerizable compounds.
PB  - Springer/Plenum Publishers, New York
T2  - Structural Chemistry
T1  - Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study
EP  - 2457
IS  - 6
SP  - 2447
VL  - 30
DO  - 10.1007/s11224-019-01371-4
ER  - 
@article{
author = "Assaleh, Mohamed H. and Božić, Aleksandra R. and Bjelogrlić, Snežana K. and Milošević, Milena D. and Simić, Milena R. and Marinković, Aleksandar and Cvijetić, Ilija",
year = "2019",
abstract = "Thiocarbohydrazones (TCHs) and structurally related molecules are versatile organic compounds which exert antioxidant, anticancer, and other beneficial health effects. The combination of UV/Vis, NMR spectroscopy, and quantum chemical calculations was used to rationalize the experimentally observed increase in the radical scavenging activity upon the addition of water in DMSO solution of TCHs. Mono- and bis(salicylaldehyde) TCHs (compounds 1 and 2) undergo water-induced E-to-Z isomerization which is followed by disruption of intramolecular hydrogen bond, ground state destabilization, and 11 kcal/mol decrease in the bond dissociation enthalpy (BDE). Electron spin delocalization is more pronounced in Z-isomers of 1 and 2. On the other hand, 2-acetylpyridine TCHs (compounds 3 and 4) undergo thione-to-thiol tautomerism which also decreases the BDE and facilitates the hydrogen atom transfer to 2,2-diphenyl-1-picrylhydrazyl radical (DPPH.). The appearance of thiolic -SH group as another reactive site toward free radicals improves the antioxidant activity of 3 and 4. The spin density of 3- and 4-thiol radicals is delocalized over the entire thiocarbohydrazide moiety compared to more localized spin of thione radicals. Additional stabilization of thiol radicals corroborates with the increased antioxidant activity. This study provides the new insights on the solution structure of TCHs, and also highlights the importance of solution structure determination when studying the structure-antioxidant relationships of isomerizable compounds.",
publisher = "Springer/Plenum Publishers, New York",
journal = "Structural Chemistry",
title = "Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study",
pages = "2457-2447",
number = "6",
volume = "30",
doi = "10.1007/s11224-019-01371-4"
}
Assaleh, M. H., Božić, A. R., Bjelogrlić, S. K., Milošević, M. D., Simić, M. R., Marinković, A.,& Cvijetić, I.. (2019). Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study. in Structural Chemistry
Springer/Plenum Publishers, New York., 30(6), 2447-2457.
https://doi.org/10.1007/s11224-019-01371-4
Assaleh MH, Božić AR, Bjelogrlić SK, Milošević MD, Simić MR, Marinković A, Cvijetić I. Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study. in Structural Chemistry. 2019;30(6):2447-2457.
doi:10.1007/s11224-019-01371-4 .
Assaleh, Mohamed H., Božić, Aleksandra R., Bjelogrlić, Snežana K., Milošević, Milena D., Simić, Milena R., Marinković, Aleksandar, Cvijetić, Ilija, "Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study" in Structural Chemistry, 30, no. 6 (2019):2447-2457,
https://doi.org/10.1007/s11224-019-01371-4 . .
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Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment-Independent 3D QSAR Models

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

(Wiley-VCH Verlag Gmbh, Weinheim, 2018)

TY  - JOUR
AU  - Božić, Aleksandra R.
AU  - Bjelogrlić, Snežana K.
AU  - Novaković, Irena T.
AU  - Filipović, Nenad R.
AU  - Petrović, Predrag
AU  - Marinković, Aleksandar
AU  - Todorović, Tamara
AU  - Cvijetić, Ilija
PY  - 2018
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3957
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-VCH 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 K. and Novaković, Irena T. and Filipović, Nenad R. and Petrović, Predrag and Marinković, Aleksandar and Todorović, Tamara and Cvijetić, Ilija",
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-VCH 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. K., Novaković, I. T., Filipović, N. R., Petrović, P., Marinković, A., Todorović, T.,& Cvijetić, I.. (2018). Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment-Independent 3D QSAR Models. in Chemistryselect
Wiley-VCH Verlag Gmbh, Weinheim., 3(7), 2215-2221.
https://doi.org/10.1002/slct.201702691
Božić AR, Bjelogrlić SK, Novaković IT, Filipović NR, Petrović P, Marinković A, Todorović T, Cvijetić I. 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 K., Novaković, Irena T., Filipović, Nenad R., Petrović, Predrag, Marinković, Aleksandar, Todorović, Tamara, Cvijetić, Ilija, "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 . .
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Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues

Filipović, Nenad R.; Elshaflu, Hana; Grubišić, Sonja; Jovanović, Ljiljana S.; Rodić, Marko; Novaković, Irena T.; Malešević, Aleksandar; Đorđević, Ivana S.; Li, Haidong; Šojić, Nešo; Marinković, Aleksandar; Todorović, Tamara

(Royal Soc Chemistry, Cambridge, 2017)

TY  - JOUR
AU  - Filipović, Nenad R.
AU  - Elshaflu, Hana
AU  - Grubišić, Sonja
AU  - Jovanović, Ljiljana S.
AU  - Rodić, Marko
AU  - Novaković, Irena T.
AU  - Malešević, Aleksandar
AU  - Đorđević, Ivana S.
AU  - Li, Haidong
AU  - Šojić, Nešo
AU  - Marinković, Aleksandar
AU  - Todorović, Tamara
PY  - 2017
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3695
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 R. and Elshaflu, Hana and Grubišić, Sonja and Jovanović, Ljiljana S. and Rodić, Marko and Novaković, Irena T. and Malešević, Aleksandar and Đorđević, Ivana S. and Li, Haidong and Šojić, Nešo and Marinković, Aleksandar and Todorović, Tamara",
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. R., Elshaflu, H., Grubišić, S., Jovanović, L. S., Rodić, M., Novaković, I. T., Malešević, A., Đorđević, I. S., Li, H., Šojić, N., Marinković, A.,& Todorović, T.. (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 NR, Elshaflu H, Grubišić S, Jovanović LS, Rodić M, Novaković IT, Malešević A, Đorđević IS, Li H, Šojić N, Marinković A, Todorović T. 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 R., Elshaflu, Hana, Grubišić, Sonja, Jovanović, Ljiljana S., Rodić, Marko, Novaković, Irena T., Malešević, Aleksandar, Đorđević, Ivana S., Li, Haidong, Šojić, Nešo, Marinković, Aleksandar, Todorović, Tamara, "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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Quinoline based mono- and bis-(thio) carbohydrazones: synthesis, anticancer activity in 2D and 3D cancer and cancer stem cell models

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

(Royal Society of Chemistry, 2016)

TY  - JOUR
AU  - Božić, Aleksandra R.
AU  - Marinković, Aleksandar
AU  - Bjelogrlić, Snežana K.
AU  - Todorović, Tamara
AU  - Cvijetić, Ilija
AU  - Novaković, Irena T.
AU  - Muller, Christian D.
AU  - Filipović, Nenad R.
PY  - 2016
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3325
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 Society of Chemistry
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 R. and Marinković, Aleksandar and Bjelogrlić, Snežana K. and Todorović, Tamara and Cvijetić, Ilija and Novaković, Irena T. and Muller, Christian D. and Filipović, Nenad R.",
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 Society of Chemistry",
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. R., Marinković, A., Bjelogrlić, S. K., Todorović, T., Cvijetić, I., Novaković, I. T., Muller, C. D.,& Filipović, N. R.. (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 Society of Chemistry., 6(106), 104763-104781.
https://doi.org/10.1039/c6ra23940d
Božić AR, Marinković A, Bjelogrlić SK, Todorović T, Cvijetić I, Novaković IT, Muller CD, Filipović NR. 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 R., Marinković, Aleksandar, Bjelogrlić, Snežana K., Todorović, Tamara, Cvijetić, Ilija, Novaković, Irena T., Muller, Christian D., Filipović, Nenad R., "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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Co(III) complex with (E)-2-(2-(pyridine-2-ylmethylene)hydrazinyl)-4-(4-tolyl)-1,3-thiazole: structure and activity against 2-D and 3-D cancer cell models

Elshaflu, Hana; Bjelogrlić, Snežana K.; Muller, Christian D.; Todorović, Tamara; Rodić, Marko; Marinković, Aleksandar; Filipović, Nenad R.

(Taylor & Francis Ltd, Abingdon, 2016)

TY  - JOUR
AU  - Elshaflu, Hana
AU  - Bjelogrlić, Snežana K.
AU  - Muller, Christian D.
AU  - Todorović, Tamara
AU  - Rodić, Marko
AU  - Marinković, Aleksandar
AU  - Filipović, Nenad R.
PY  - 2016
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3327
AB  - Co(III) complex with a 2-hydrazonylthiazole ligand was synthesized and characterized by single-crystal X-ray diffraction. In the inner sphere of the complex, two monoionic ligands are coordinated tridentately forming octahedral geometry around Co(III). Activity of the complex was investigated on MCF-7 breast cancer cell line, with cisplatin (CDDP) as a reference compound. Results showed that after 24-h incubation, Co(III) complex revealed stronger cytotoxic activity compared to CDDP. Treatment of MCF-7 3-D cell model with the complex at 10M concentration achieved complete suppression of spheroid growth in almost the same extent as at 100M. In combination treatments on MCF-7 spheroids, the complex acted synergistically with CDDP, while additive interaction type was achieved when the complex was applied together with paclitaxel. [GRAPHICS] .
PB  - Taylor & Francis Ltd, Abingdon
T2  - Journal of Coordination Chemistry
T1  - Co(III) complex with (E)-2-(2-(pyridine-2-ylmethylene)hydrazinyl)-4-(4-tolyl)-1,3-thiazole: structure and activity against 2-D and 3-D cancer cell models
EP  - 3366
IS  - 22
SP  - 3354
VL  - 69
DO  - 10.1080/00958972.2016.1232404
ER  - 
@article{
author = "Elshaflu, Hana and Bjelogrlić, Snežana K. and Muller, Christian D. and Todorović, Tamara and Rodić, Marko and Marinković, Aleksandar and Filipović, Nenad R.",
year = "2016",
abstract = "Co(III) complex with a 2-hydrazonylthiazole ligand was synthesized and characterized by single-crystal X-ray diffraction. In the inner sphere of the complex, two monoionic ligands are coordinated tridentately forming octahedral geometry around Co(III). Activity of the complex was investigated on MCF-7 breast cancer cell line, with cisplatin (CDDP) as a reference compound. Results showed that after 24-h incubation, Co(III) complex revealed stronger cytotoxic activity compared to CDDP. Treatment of MCF-7 3-D cell model with the complex at 10M concentration achieved complete suppression of spheroid growth in almost the same extent as at 100M. In combination treatments on MCF-7 spheroids, the complex acted synergistically with CDDP, while additive interaction type was achieved when the complex was applied together with paclitaxel. [GRAPHICS] .",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Journal of Coordination Chemistry",
title = "Co(III) complex with (E)-2-(2-(pyridine-2-ylmethylene)hydrazinyl)-4-(4-tolyl)-1,3-thiazole: structure and activity against 2-D and 3-D cancer cell models",
pages = "3366-3354",
number = "22",
volume = "69",
doi = "10.1080/00958972.2016.1232404"
}
Elshaflu, H., Bjelogrlić, S. K., Muller, C. D., Todorović, T., Rodić, M., Marinković, A.,& Filipović, N. R.. (2016). Co(III) complex with (E)-2-(2-(pyridine-2-ylmethylene)hydrazinyl)-4-(4-tolyl)-1,3-thiazole: structure and activity against 2-D and 3-D cancer cell models. in Journal of Coordination Chemistry
Taylor & Francis Ltd, Abingdon., 69(22), 3354-3366.
https://doi.org/10.1080/00958972.2016.1232404
Elshaflu H, Bjelogrlić SK, Muller CD, Todorović T, Rodić M, Marinković A, Filipović NR. Co(III) complex with (E)-2-(2-(pyridine-2-ylmethylene)hydrazinyl)-4-(4-tolyl)-1,3-thiazole: structure and activity against 2-D and 3-D cancer cell models. in Journal of Coordination Chemistry. 2016;69(22):3354-3366.
doi:10.1080/00958972.2016.1232404 .
Elshaflu, Hana, Bjelogrlić, Snežana K., Muller, Christian D., Todorović, Tamara, Rodić, Marko, Marinković, Aleksandar, Filipović, Nenad R., "Co(III) complex with (E)-2-(2-(pyridine-2-ylmethylene)hydrazinyl)-4-(4-tolyl)-1,3-thiazole: structure and activity against 2-D and 3-D cancer cell models" in Journal of Coordination Chemistry, 69, no. 22 (2016):3354-3366,
https://doi.org/10.1080/00958972.2016.1232404 . .
18
10
17

Co(III) complex with (E)-2-(2-(pyridine-2-ylmethylene)hydrazinyl)-4-(4-tolyl)-1,3-thiazole: structure and activity against 2-D and 3-D cancer cell models

Elshaflu, Hana; Bjelogrlić, Snežana K.; Muller, Christian D.; Todorović, Tamara; Rodić, Marko; Marinković, Aleksandar; Filipović, Nenad R.

(Taylor & Francis Ltd, Abingdon, 2016)

TY  - JOUR
AU  - Elshaflu, Hana
AU  - Bjelogrlić, Snežana K.
AU  - Muller, Christian D.
AU  - Todorović, Tamara
AU  - Rodić, Marko
AU  - Marinković, Aleksandar
AU  - Filipović, Nenad R.
PY  - 2016
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4721
AB  - Co(III) complex with a 2-hydrazonylthiazole ligand was synthesized and characterized by single-crystal X-ray diffraction. In the inner sphere of the complex, two monoionic ligands are coordinated tridentately forming octahedral geometry around Co(III). Activity of the complex was investigated on MCF-7 breast cancer cell line, with cisplatin (CDDP) as a reference compound. Results showed that after 24-h incubation, Co(III) complex revealed stronger cytotoxic activity compared to CDDP. Treatment of MCF-7 3-D cell model with the complex at 10M concentration achieved complete suppression of spheroid growth in almost the same extent as at 100M. In combination treatments on MCF-7 spheroids, the complex acted synergistically with CDDP, while additive interaction type was achieved when the complex was applied together with paclitaxel.
PB  - Taylor & Francis Ltd, Abingdon
T2  - Journal of Coordination Chemistry
T1  - Co(III) complex with (E)-2-(2-(pyridine-2-ylmethylene)hydrazinyl)-4-(4-tolyl)-1,3-thiazole: structure and activity against 2-D and 3-D cancer cell models
EP  - 3366
IS  - 22
SP  - 3354
VL  - 69
DO  - 10.1080/00958972.2016.1232404
ER  - 
@article{
author = "Elshaflu, Hana and Bjelogrlić, Snežana K. and Muller, Christian D. and Todorović, Tamara and Rodić, Marko and Marinković, Aleksandar and Filipović, Nenad R.",
year = "2016",
abstract = "Co(III) complex with a 2-hydrazonylthiazole ligand was synthesized and characterized by single-crystal X-ray diffraction. In the inner sphere of the complex, two monoionic ligands are coordinated tridentately forming octahedral geometry around Co(III). Activity of the complex was investigated on MCF-7 breast cancer cell line, with cisplatin (CDDP) as a reference compound. Results showed that after 24-h incubation, Co(III) complex revealed stronger cytotoxic activity compared to CDDP. Treatment of MCF-7 3-D cell model with the complex at 10M concentration achieved complete suppression of spheroid growth in almost the same extent as at 100M. In combination treatments on MCF-7 spheroids, the complex acted synergistically with CDDP, while additive interaction type was achieved when the complex was applied together with paclitaxel.",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Journal of Coordination Chemistry",
title = "Co(III) complex with (E)-2-(2-(pyridine-2-ylmethylene)hydrazinyl)-4-(4-tolyl)-1,3-thiazole: structure and activity against 2-D and 3-D cancer cell models",
pages = "3366-3354",
number = "22",
volume = "69",
doi = "10.1080/00958972.2016.1232404"
}
Elshaflu, H., Bjelogrlić, S. K., Muller, C. D., Todorović, T., Rodić, M., Marinković, A.,& Filipović, N. R.. (2016). Co(III) complex with (E)-2-(2-(pyridine-2-ylmethylene)hydrazinyl)-4-(4-tolyl)-1,3-thiazole: structure and activity against 2-D and 3-D cancer cell models. in Journal of Coordination Chemistry
Taylor & Francis Ltd, Abingdon., 69(22), 3354-3366.
https://doi.org/10.1080/00958972.2016.1232404
Elshaflu H, Bjelogrlić SK, Muller CD, Todorović T, Rodić M, Marinković A, Filipović NR. Co(III) complex with (E)-2-(2-(pyridine-2-ylmethylene)hydrazinyl)-4-(4-tolyl)-1,3-thiazole: structure and activity against 2-D and 3-D cancer cell models. in Journal of Coordination Chemistry. 2016;69(22):3354-3366.
doi:10.1080/00958972.2016.1232404 .
Elshaflu, Hana, Bjelogrlić, Snežana K., Muller, Christian D., Todorović, Tamara, Rodić, Marko, Marinković, Aleksandar, Filipović, Nenad R., "Co(III) complex with (E)-2-(2-(pyridine-2-ylmethylene)hydrazinyl)-4-(4-tolyl)-1,3-thiazole: structure and activity against 2-D and 3-D cancer cell models" in Journal of Coordination Chemistry, 69, no. 22 (2016):3354-3366,
https://doi.org/10.1080/00958972.2016.1232404 . .
18
10
17

Ni(II) complex with bishydrazone ligand: synthesis, characterization, DNA binding studies and pro-apoptotic and pro-differentiation induction in human cancerous cell lines

Filipović, Nenad R.; Bjelogrlić, Snežana K.; Todorović, Tamara; Blagojević, Vladimir A.; Muller, Christian D.; Marinković, Aleksandar; Vujčić, Miroslava T.; Janović, Barbara S.; Malešević, Aleksandar; Begović, Nebojša; Senćanski, Milan V.; Minić, Dragica M.

(Royal Soc Chemistry, Cambridge, 2016)

TY  - JOUR
AU  - Filipović, Nenad R.
AU  - Bjelogrlić, Snežana K.
AU  - Todorović, Tamara
AU  - Blagojević, Vladimir A.
AU  - Muller, Christian D.
AU  - Marinković, Aleksandar
AU  - Vujčić, Miroslava T.
AU  - Janović, Barbara S.
AU  - Malešević, Aleksandar
AU  - Begović, Nebojša
AU  - Senćanski, Milan V.
AU  - Minić, Dragica M.
PY  - 2016
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3315
AB  - A new Ni(II) complex, [Ni(L)(H2O)] (1), with diethyl 3,3'-(2,2'-(1,1'-(pyridine-2,6-diyl) bis(ethan-1-yl-1-ylidene)) bis(hydrazin-1-yl-2-ylidene)) bis(3-oxopropanoate) ligand (H2L) was synthesized as a potential chemotherapeutic agent. Polidentate ligand was coordinated to Ni(II) NNN-tridentately, in dianionic form, while monodentate water coordination completed square-planar geometry around metal. Structure in the solution was determined by NMR spectroscopy and the same coordination mode was observed in the solid state using IR spectroscopy and further verified by DFT calculations and electrochemical studies. Thermal stability of 1 was determined in both air and nitrogen atmosphere. Anticancer activity of 1 was investigated on acute monocytic leukemia (THP-1) and pancreatic adenocarcinoma (AsPC-1) cell lines. On THP-1 cells 1 induced powerful apoptotic response (ED50 = 10 +/- 3 mu M), which was revealed to be only partially caspase-dependent, with activation of caspase-8 as the dominant course. This suggested that experimentally validated covalent binding of 1 to DNA is not the only mechanism responsible for programmed cell death. This was supported with experiments on AsPC-1 cells. Although treatment of those cells with 1 resulted in poor apoptotic response, cell cycle changes showed concentration-dependent shifts indicating a dual mechanism of activity. This study also reviews the results of preliminary biological screening, which demonstrates that 1 displays a unique pattern of anticancer activity with at least two mechanisms involved.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Ni(II) complex with bishydrazone ligand: synthesis, characterization, DNA binding studies and pro-apoptotic and pro-differentiation induction in human cancerous cell lines
EP  - 108740
IS  - 110
SP  - 108726
VL  - 6
DO  - 10.1039/c6ra24604d
ER  - 
@article{
author = "Filipović, Nenad R. and Bjelogrlić, Snežana K. and Todorović, Tamara and Blagojević, Vladimir A. and Muller, Christian D. and Marinković, Aleksandar and Vujčić, Miroslava T. and Janović, Barbara S. and Malešević, Aleksandar and Begović, Nebojša and Senćanski, Milan V. and Minić, Dragica M.",
year = "2016",
abstract = "A new Ni(II) complex, [Ni(L)(H2O)] (1), with diethyl 3,3'-(2,2'-(1,1'-(pyridine-2,6-diyl) bis(ethan-1-yl-1-ylidene)) bis(hydrazin-1-yl-2-ylidene)) bis(3-oxopropanoate) ligand (H2L) was synthesized as a potential chemotherapeutic agent. Polidentate ligand was coordinated to Ni(II) NNN-tridentately, in dianionic form, while monodentate water coordination completed square-planar geometry around metal. Structure in the solution was determined by NMR spectroscopy and the same coordination mode was observed in the solid state using IR spectroscopy and further verified by DFT calculations and electrochemical studies. Thermal stability of 1 was determined in both air and nitrogen atmosphere. Anticancer activity of 1 was investigated on acute monocytic leukemia (THP-1) and pancreatic adenocarcinoma (AsPC-1) cell lines. On THP-1 cells 1 induced powerful apoptotic response (ED50 = 10 +/- 3 mu M), which was revealed to be only partially caspase-dependent, with activation of caspase-8 as the dominant course. This suggested that experimentally validated covalent binding of 1 to DNA is not the only mechanism responsible for programmed cell death. This was supported with experiments on AsPC-1 cells. Although treatment of those cells with 1 resulted in poor apoptotic response, cell cycle changes showed concentration-dependent shifts indicating a dual mechanism of activity. This study also reviews the results of preliminary biological screening, which demonstrates that 1 displays a unique pattern of anticancer activity with at least two mechanisms involved.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Ni(II) complex with bishydrazone ligand: synthesis, characterization, DNA binding studies and pro-apoptotic and pro-differentiation induction in human cancerous cell lines",
pages = "108740-108726",
number = "110",
volume = "6",
doi = "10.1039/c6ra24604d"
}
Filipović, N. R., Bjelogrlić, S. K., Todorović, T., Blagojević, V. A., Muller, C. D., Marinković, A., Vujčić, M. T., Janović, B. S., Malešević, A., Begović, N., Senćanski, M. V.,& Minić, D. M.. (2016). Ni(II) complex with bishydrazone ligand: synthesis, characterization, DNA binding studies and pro-apoptotic and pro-differentiation induction in human cancerous cell lines. in RSC Advances
Royal Soc Chemistry, Cambridge., 6(110), 108726-108740.
https://doi.org/10.1039/c6ra24604d
Filipović NR, Bjelogrlić SK, Todorović T, Blagojević VA, Muller CD, Marinković A, Vujčić MT, Janović BS, Malešević A, Begović N, Senćanski MV, Minić DM. Ni(II) complex with bishydrazone ligand: synthesis, characterization, DNA binding studies and pro-apoptotic and pro-differentiation induction in human cancerous cell lines. in RSC Advances. 2016;6(110):108726-108740.
doi:10.1039/c6ra24604d .
Filipović, Nenad R., Bjelogrlić, Snežana K., Todorović, Tamara, Blagojević, Vladimir A., Muller, Christian D., Marinković, Aleksandar, Vujčić, Miroslava T., Janović, Barbara S., Malešević, Aleksandar, Begović, Nebojša, Senćanski, Milan V., Minić, Dragica M., "Ni(II) complex with bishydrazone ligand: synthesis, characterization, DNA binding studies and pro-apoptotic and pro-differentiation induction in human cancerous cell lines" in RSC Advances, 6, no. 110 (2016):108726-108740,
https://doi.org/10.1039/c6ra24604d . .
16
12
16

Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction

Filipović, Nenad R.; Bjelogrlić, Snežana K.; Marinković, Aleksandar; Verbić, Tatjana; Cvijetić, Ilija; Senćanski, Milan V.; Rodić, Marko; Vujčić, Miroslava T.; Sladić, Dušan M.; Striković, Zlatko; Todorović, Tamara; Muller, Christian D.

(Royal Society of Chemistry, 2015)

TY  - JOUR
AU  - Filipović, Nenad R.
AU  - Bjelogrlić, Snežana K.
AU  - Marinković, Aleksandar
AU  - Verbić, Tatjana
AU  - Cvijetić, Ilija
AU  - Senćanski, Milan V.
AU  - Rodić, Marko
AU  - Vujčić, Miroslava T.
AU  - Sladić, Dušan M.
AU  - Striković, Zlatko
AU  - Todorović, Tamara
AU  - Muller, Christian D.
PY  - 2015
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3058
AB  - A new Zn(II)-based potential chemotherapeutic agent was synthesized from the ligand 2-quinolinecarboxaldehyde selenosemicarbazone (Hqasesc). Single crystal X-ray diffraction analysis showed that the Zn(II) complex consists of a cation [Zn(Hqasesc)(2)](2+), two perchlorate anions and one ethanol solvent molecule. The interaction of calf thymus (CT) DNA and human serum albumin (HSA) with the Zn(II) complex was explored using absorption and emission spectral methods, and also has been supported by molecular docking studies. The complex has more affinity to minor DNA groove than major, with no significant intercalation. The HSA interaction studies of the complex revealed the quenching of the intrinsic fluorescence of the HSA through a static quenching mechanism. The antitumor activity of the ligand and the complex against pancreatic adenocarcinoma cell line (AsPC-1) and acute monocytic leukemia (THP-1) cells was evaluated. Both compounds are strong concentration-dependent apoptosis inducers in THP-1 cells. While Hqasesc in AsPC-1 cells induces apoptosis only at the highest concentration, treatment with the Zn complex shows a concentration-dependent apoptotic response, where the treated cells are arrested in the G1-to-S phase accompanied with extensive activation of caspase-8 and -9. These results indicate that the ligand and Zn(II) complex display cell phenotype specific activity.
PB  - Royal Society of Chemistry
T2  - RSC Advances
T1  - Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction
EP  - 95211
IS  - 115
SP  - 95191
VL  - 5
DO  - 10.1039/c5ra19849f
ER  - 
@article{
author = "Filipović, Nenad R. and Bjelogrlić, Snežana K. and Marinković, Aleksandar and Verbić, Tatjana and Cvijetić, Ilija and Senćanski, Milan V. and Rodić, Marko and Vujčić, Miroslava T. and Sladić, Dušan M. and Striković, Zlatko and Todorović, Tamara and Muller, Christian D.",
year = "2015",
abstract = "A new Zn(II)-based potential chemotherapeutic agent was synthesized from the ligand 2-quinolinecarboxaldehyde selenosemicarbazone (Hqasesc). Single crystal X-ray diffraction analysis showed that the Zn(II) complex consists of a cation [Zn(Hqasesc)(2)](2+), two perchlorate anions and one ethanol solvent molecule. The interaction of calf thymus (CT) DNA and human serum albumin (HSA) with the Zn(II) complex was explored using absorption and emission spectral methods, and also has been supported by molecular docking studies. The complex has more affinity to minor DNA groove than major, with no significant intercalation. The HSA interaction studies of the complex revealed the quenching of the intrinsic fluorescence of the HSA through a static quenching mechanism. The antitumor activity of the ligand and the complex against pancreatic adenocarcinoma cell line (AsPC-1) and acute monocytic leukemia (THP-1) cells was evaluated. Both compounds are strong concentration-dependent apoptosis inducers in THP-1 cells. While Hqasesc in AsPC-1 cells induces apoptosis only at the highest concentration, treatment with the Zn complex shows a concentration-dependent apoptotic response, where the treated cells are arrested in the G1-to-S phase accompanied with extensive activation of caspase-8 and -9. These results indicate that the ligand and Zn(II) complex display cell phenotype specific activity.",
publisher = "Royal Society of Chemistry",
journal = "RSC Advances",
title = "Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction",
pages = "95211-95191",
number = "115",
volume = "5",
doi = "10.1039/c5ra19849f"
}
Filipović, N. R., Bjelogrlić, S. K., Marinković, A., Verbić, T., Cvijetić, I., Senćanski, M. V., Rodić, M., Vujčić, M. T., Sladić, D. M., Striković, Z., Todorović, T.,& Muller, C. D.. (2015). Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction. in RSC Advances
Royal Society of Chemistry., 5(115), 95191-95211.
https://doi.org/10.1039/c5ra19849f
Filipović NR, Bjelogrlić SK, Marinković A, Verbić T, Cvijetić I, Senćanski MV, Rodić M, Vujčić MT, Sladić DM, Striković Z, Todorović T, Muller CD. Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction. in RSC Advances. 2015;5(115):95191-95211.
doi:10.1039/c5ra19849f .
Filipović, Nenad R., Bjelogrlić, Snežana K., Marinković, Aleksandar, Verbić, Tatjana, Cvijetić, Ilija, Senćanski, Milan V., Rodić, Marko, Vujčić, Miroslava T., Sladić, Dušan M., Striković, Zlatko, Todorović, Tamara, Muller, Christian D., "Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction" in RSC Advances, 5, no. 115 (2015):95191-95211,
https://doi.org/10.1039/c5ra19849f . .
32
27
33

Palladium(II) Complexes with N-Heteroaromatic Bidentate Hydrazone Ligands: The Effect of the Chelate Ring Size and Lipophilicity on in vitro Cytotoxic Activity

Filipović, Nenad R.; Grubišić, Sonja; Jovanović, Maja; Dulović, Marija; Marković, Ivanka; Klisurić, Olivera; Marinković, Aleksandar; Mitić, Dragana; Anđelković, Katarina K.; Todorović, Tamara

(Wiley, Hoboken, 2014)

TY  - JOUR
AU  - Filipović, Nenad R.
AU  - Grubišić, Sonja
AU  - Jovanović, Maja
AU  - Dulović, Marija
AU  - Marković, Ivanka
AU  - Klisurić, Olivera
AU  - Marinković, Aleksandar
AU  - Mitić, Dragana
AU  - Anđelković, Katarina K.
AU  - Todorović, Tamara
PY  - 2014
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2733
AB  - Novel Pd(II) complex with N-heteroaromatic Schiff base ligand, derived from 8-quinolinecarboxaldehyde (q8a) and ethyl hydrazinoacetate (haOEt), was synthesized and characterized by analytical and spectroscopy methods. The structure of novel complex, as well as structures of its quinoline and pyridine analogues, was optimized by density functional theory calculations, and theoretical data show good agreement with experimental results. A cytotoxic action of the complexes was evaluated on cultures of human promyelocytic leukemia (HL-60), human glioma (U251), rat glioma (C6), and mouse fibrosarcoma (L929) cell lines. Among investigated compounds, only complexes with quinoline-based ligands reduce the cell numbers in a dose-dependent manner in investigated cell lines. The observed cytotoxic effect of two isomeric quinoline-based complexes is predominantly mediated through the induction of apoptotic cell death in HL-60 cell line. The cytotoxicity of most efficient novel Pd(II) complex is comparable to the activity of cisplatin, in all cell lines investigated.
PB  - Wiley, Hoboken
T2  - Chemical Biology & Drug Design
T1  - Palladium(II) Complexes with N-Heteroaromatic Bidentate Hydrazone Ligands: The Effect of the Chelate Ring Size and Lipophilicity on in vitro Cytotoxic Activity
EP  - 341
IS  - 3
SP  - 333
VL  - 84
DO  - 10.1111/cbdd.12322
ER  - 
@article{
author = "Filipović, Nenad R. and Grubišić, Sonja and Jovanović, Maja and Dulović, Marija and Marković, Ivanka and Klisurić, Olivera and Marinković, Aleksandar and Mitić, Dragana and Anđelković, Katarina K. and Todorović, Tamara",
year = "2014",
abstract = "Novel Pd(II) complex with N-heteroaromatic Schiff base ligand, derived from 8-quinolinecarboxaldehyde (q8a) and ethyl hydrazinoacetate (haOEt), was synthesized and characterized by analytical and spectroscopy methods. The structure of novel complex, as well as structures of its quinoline and pyridine analogues, was optimized by density functional theory calculations, and theoretical data show good agreement with experimental results. A cytotoxic action of the complexes was evaluated on cultures of human promyelocytic leukemia (HL-60), human glioma (U251), rat glioma (C6), and mouse fibrosarcoma (L929) cell lines. Among investigated compounds, only complexes with quinoline-based ligands reduce the cell numbers in a dose-dependent manner in investigated cell lines. The observed cytotoxic effect of two isomeric quinoline-based complexes is predominantly mediated through the induction of apoptotic cell death in HL-60 cell line. The cytotoxicity of most efficient novel Pd(II) complex is comparable to the activity of cisplatin, in all cell lines investigated.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology & Drug Design",
title = "Palladium(II) Complexes with N-Heteroaromatic Bidentate Hydrazone Ligands: The Effect of the Chelate Ring Size and Lipophilicity on in vitro Cytotoxic Activity",
pages = "341-333",
number = "3",
volume = "84",
doi = "10.1111/cbdd.12322"
}
Filipović, N. R., Grubišić, S., Jovanović, M., Dulović, M., Marković, I., Klisurić, O., Marinković, A., Mitić, D., Anđelković, K. K.,& Todorović, T.. (2014). Palladium(II) Complexes with N-Heteroaromatic Bidentate Hydrazone Ligands: The Effect of the Chelate Ring Size and Lipophilicity on in vitro Cytotoxic Activity. in Chemical Biology & Drug Design
Wiley, Hoboken., 84(3), 333-341.
https://doi.org/10.1111/cbdd.12322
Filipović NR, Grubišić S, Jovanović M, Dulović M, Marković I, Klisurić O, Marinković A, Mitić D, Anđelković KK, Todorović T. Palladium(II) Complexes with N-Heteroaromatic Bidentate Hydrazone Ligands: The Effect of the Chelate Ring Size and Lipophilicity on in vitro Cytotoxic Activity. in Chemical Biology & Drug Design. 2014;84(3):333-341.
doi:10.1111/cbdd.12322 .
Filipović, Nenad R., Grubišić, Sonja, Jovanović, Maja, Dulović, Marija, Marković, Ivanka, Klisurić, Olivera, Marinković, Aleksandar, Mitić, Dragana, Anđelković, Katarina K., Todorović, Tamara, "Palladium(II) Complexes with N-Heteroaromatic Bidentate Hydrazone Ligands: The Effect of the Chelate Ring Size and Lipophilicity on in vitro Cytotoxic Activity" in Chemical Biology & Drug Design, 84, no. 3 (2014):333-341,
https://doi.org/10.1111/cbdd.12322 . .
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Kinetics and mechanism of degradation of Co(II)-N-benzyloxycarbonylglycinato complex

Minić, Dragica M.; Šumar-Ristović, Maja; Miodragović Đenana U.; Anđelković, Katarina K.; Poleti, Dejan

(Springer, Dordrecht, 2012)

TY  - JOUR
AU  - Minić, Dragica M.
AU  - Šumar-Ristović, Maja
AU  - Miodragović Đenana U.
AU  - Anđelković, Katarina K.
AU  - Poleti, Dejan
PY  - 2012
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5695
AB  - The kinetics of multi-step thermal degradation of Co(II) complex with N-benzyloxycarbonyl glycinato ligand [Co(N-Boc-gly)(2)(H2O)(4)]center dot 2H(2)O, in non-isothermal conditions was studied using isoconversional and non-isoconversional methods. The degradation of complex occurs in three well-separated steps involving the loss of water molecules in first step followed by two degradation steps of dehydrated complex. The dependence of Arrhenius parameters on conversion degree showed that all observed steps of thermal degradation are very complex, involving more than one elementary step, as can be expected for most solid-state heterogeneous reactions with solid reactants and solid and gaseous products. It was shown that step 1, corresponding to the dehydration, involves a series of competitive dehydration steps of differently bound water molecules complicated by diffusion. Second step involves two parallel reactions related to the loss of two identical C6H5CH2O-ligand fragments complicated by the presence of products in gaseous state. Further degradation in step 3 corresponds to complex process with a change in the limiting stage, in this case from the kinetic to the diffusion regime, connected with the presence of gaseous products diffusing through the solid product.
PB  - Springer, Dordrecht
T2  - Journal of Thermal Analysis and Calorimetry
T1  - Kinetics and mechanism of degradation of Co(II)-N-benzyloxycarbonylglycinato complex
EP  - 1176
IS  - 3
SP  - 1167
VL  - 107
DO  - 10.1007/s10973-011-1368-1
ER  - 
@article{
author = "Minić, Dragica M. and Šumar-Ristović, Maja and Miodragović Đenana U. and Anđelković, Katarina K. and Poleti, Dejan",
year = "2012",
abstract = "The kinetics of multi-step thermal degradation of Co(II) complex with N-benzyloxycarbonyl glycinato ligand [Co(N-Boc-gly)(2)(H2O)(4)]center dot 2H(2)O, in non-isothermal conditions was studied using isoconversional and non-isoconversional methods. The degradation of complex occurs in three well-separated steps involving the loss of water molecules in first step followed by two degradation steps of dehydrated complex. The dependence of Arrhenius parameters on conversion degree showed that all observed steps of thermal degradation are very complex, involving more than one elementary step, as can be expected for most solid-state heterogeneous reactions with solid reactants and solid and gaseous products. It was shown that step 1, corresponding to the dehydration, involves a series of competitive dehydration steps of differently bound water molecules complicated by diffusion. Second step involves two parallel reactions related to the loss of two identical C6H5CH2O-ligand fragments complicated by the presence of products in gaseous state. Further degradation in step 3 corresponds to complex process with a change in the limiting stage, in this case from the kinetic to the diffusion regime, connected with the presence of gaseous products diffusing through the solid product.",
publisher = "Springer, Dordrecht",
journal = "Journal of Thermal Analysis and Calorimetry",
title = "Kinetics and mechanism of degradation of Co(II)-N-benzyloxycarbonylglycinato complex",
pages = "1176-1167",
number = "3",
volume = "107",
doi = "10.1007/s10973-011-1368-1"
}
Minić, D. M., Šumar-Ristović, M., Miodragović Đenana U., Anđelković, K. K.,& Poleti, D.. (2012). Kinetics and mechanism of degradation of Co(II)-N-benzyloxycarbonylglycinato complex. in Journal of Thermal Analysis and Calorimetry
Springer, Dordrecht., 107(3), 1167-1176.
https://doi.org/10.1007/s10973-011-1368-1
Minić DM, Šumar-Ristović M, Miodragović Đenana U., Anđelković KK, Poleti D. Kinetics and mechanism of degradation of Co(II)-N-benzyloxycarbonylglycinato complex. in Journal of Thermal Analysis and Calorimetry. 2012;107(3):1167-1176.
doi:10.1007/s10973-011-1368-1 .
Minić, Dragica M., Šumar-Ristović, Maja, Miodragović Đenana U., Anđelković, Katarina K., Poleti, Dejan, "Kinetics and mechanism of degradation of Co(II)-N-benzyloxycarbonylglycinato complex" in Journal of Thermal Analysis and Calorimetry, 107, no. 3 (2012):1167-1176,
https://doi.org/10.1007/s10973-011-1368-1 . .
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Kinetics, mechanism, and DFT calculations of thermal degradation of a Zn(II) complex with N-benzyloxycarbonylglycinato ligands

Šumar-Ristović, Maja; Gruden-Pavlović, Maja; Zlatar, Matija; Blagojević, Vladimir A.; Anđelković, Katarina K.; Poleti, Dejan; Minić, Dragica M.

(Springer Wien, Wien, 2012)

TY  - JOUR
AU  - Šumar-Ristović, Maja
AU  - Gruden-Pavlović, Maja
AU  - Zlatar, Matija
AU  - Blagojević, Vladimir A.
AU  - Anđelković, Katarina K.
AU  - Poleti, Dejan
AU  - Minić, Dragica M.
PY  - 2012
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5696
AB  - A Zn(II) complex with N-benzyloxycarbonylglycinato ligands was studied by non-isothermal methods, in particular Kissinger-Akahira-Sunose's method, and further analysis of these results was performed by Vyazovkin's algorithm and an artificial compensation effect. Density functional theory calculations of thermodynamic quantities were performed, and results obtained by both methods are consistent, thus clarifying the mechanism of this very interesting multi-step degradation.
PB  - Springer Wien, Wien
T2  - Monatshefte Fur Chemie
T1  - Kinetics, mechanism, and DFT calculations of thermal degradation of a Zn(II) complex with N-benzyloxycarbonylglycinato ligands
EP  - 1139
IS  - 8
SP  - 1133
VL  - 143
DO  - 10.1007/s00706-012-0793-6
ER  - 
@article{
author = "Šumar-Ristović, Maja and Gruden-Pavlović, Maja and Zlatar, Matija and Blagojević, Vladimir A. and Anđelković, Katarina K. and Poleti, Dejan and Minić, Dragica M.",
year = "2012",
abstract = "A Zn(II) complex with N-benzyloxycarbonylglycinato ligands was studied by non-isothermal methods, in particular Kissinger-Akahira-Sunose's method, and further analysis of these results was performed by Vyazovkin's algorithm and an artificial compensation effect. Density functional theory calculations of thermodynamic quantities were performed, and results obtained by both methods are consistent, thus clarifying the mechanism of this very interesting multi-step degradation.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "Kinetics, mechanism, and DFT calculations of thermal degradation of a Zn(II) complex with N-benzyloxycarbonylglycinato ligands",
pages = "1139-1133",
number = "8",
volume = "143",
doi = "10.1007/s00706-012-0793-6"
}
Šumar-Ristović, M., Gruden-Pavlović, M., Zlatar, M., Blagojević, V. A., Anđelković, K. K., Poleti, D.,& Minić, D. M.. (2012). Kinetics, mechanism, and DFT calculations of thermal degradation of a Zn(II) complex with N-benzyloxycarbonylglycinato ligands. in Monatshefte Fur Chemie
Springer Wien, Wien., 143(8), 1133-1139.
https://doi.org/10.1007/s00706-012-0793-6
Šumar-Ristović M, Gruden-Pavlović M, Zlatar M, Blagojević VA, Anđelković KK, Poleti D, Minić DM. Kinetics, mechanism, and DFT calculations of thermal degradation of a Zn(II) complex with N-benzyloxycarbonylglycinato ligands. in Monatshefte Fur Chemie. 2012;143(8):1133-1139.
doi:10.1007/s00706-012-0793-6 .
Šumar-Ristović, Maja, Gruden-Pavlović, Maja, Zlatar, Matija, Blagojević, Vladimir A., Anđelković, Katarina K., Poleti, Dejan, Minić, Dragica M., "Kinetics, mechanism, and DFT calculations of thermal degradation of a Zn(II) complex with N-benzyloxycarbonylglycinato ligands" in Monatshefte Fur Chemie, 143, no. 8 (2012):1133-1139,
https://doi.org/10.1007/s00706-012-0793-6 . .
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Thermal degradation of coordination polymer [Cd(N-Boc-gly)(2)(H2O)(2)](n)

Šumar-Ristović, Maja; Anđelković, Katarina K.; Poleti, Dejan; Minić, Dragica M.

(Elsevier Science Bv, Amsterdam, 2011)

TY  - JOUR
AU  - Šumar-Ristović, Maja
AU  - Anđelković, Katarina K.
AU  - Poleti, Dejan
AU  - Minić, Dragica M.
PY  - 2011
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5662
AB  - Multi-step thermal degradation of coordination polymer [Cd(N-Boc-gly)(2)(H2O)(2)](n) in non-isothermal conditions was studied. The kinetic parameters were determined from the thermal decomposition data using the isoconversion and non-isoconversion techniques. It was shown that the coordination polymer is stable up to 60 C, when the multi-step process of thermal dehydration, followed by steps of degradation, starts. The kinetic triplet for the step of dehydration was established as f(alpha) = 3/2(1 - alpha)(2/3)[1 - (1 - alpha)(1/3)](-1). E-inv = 170.4 +/- 6.4 kJ mol(-1) and Z(inv) =2.6 x 10(23). The established kinetic model, known as "D3 model", was confirmed by application criteria defined by Malek, Perez-Maqueda et al. as well as Master plot method. Dehydration step is followed by two steps of dehydrated coordination polymer degradation. On the base of the dependence of Arrhenius parameters (E-a and Z) on conversion degree (alpha), the mechanisms of degradation were discussed. In this way it was shown that second and third steps of degradation of coordination polymer are complex involving more than one elementary step. The second step corresponds to the loss of two C6H5CH2O- fragments in two parallel steps. The third step of degradation, ascribed to the loss of two -C(=O)NHCH2- fragments, is complicated by changing kinetically to diffusion control. (C) 2011 Elsevier B.V. All rights reserved.
PB  - Elsevier Science Bv, Amsterdam
T2  - Thermochimica Acta
T1  - Thermal degradation of coordination polymer [Cd(N-Boc-gly)(2)(H2O)(2)](n)
EP  - 30
IS  - 1-2
SP  - 25
VL  - 525
DO  - 10.1016/j.tca.2011.07.017
ER  - 
@article{
author = "Šumar-Ristović, Maja and Anđelković, Katarina K. and Poleti, Dejan and Minić, Dragica M.",
year = "2011",
abstract = "Multi-step thermal degradation of coordination polymer [Cd(N-Boc-gly)(2)(H2O)(2)](n) in non-isothermal conditions was studied. The kinetic parameters were determined from the thermal decomposition data using the isoconversion and non-isoconversion techniques. It was shown that the coordination polymer is stable up to 60 C, when the multi-step process of thermal dehydration, followed by steps of degradation, starts. The kinetic triplet for the step of dehydration was established as f(alpha) = 3/2(1 - alpha)(2/3)[1 - (1 - alpha)(1/3)](-1). E-inv = 170.4 +/- 6.4 kJ mol(-1) and Z(inv) =2.6 x 10(23). The established kinetic model, known as "D3 model", was confirmed by application criteria defined by Malek, Perez-Maqueda et al. as well as Master plot method. Dehydration step is followed by two steps of dehydrated coordination polymer degradation. On the base of the dependence of Arrhenius parameters (E-a and Z) on conversion degree (alpha), the mechanisms of degradation were discussed. In this way it was shown that second and third steps of degradation of coordination polymer are complex involving more than one elementary step. The second step corresponds to the loss of two C6H5CH2O- fragments in two parallel steps. The third step of degradation, ascribed to the loss of two -C(=O)NHCH2- fragments, is complicated by changing kinetically to diffusion control. (C) 2011 Elsevier B.V. All rights reserved.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Thermochimica Acta",
title = "Thermal degradation of coordination polymer [Cd(N-Boc-gly)(2)(H2O)(2)](n)",
pages = "30-25",
number = "1-2",
volume = "525",
doi = "10.1016/j.tca.2011.07.017"
}
Šumar-Ristović, M., Anđelković, K. K., Poleti, D.,& Minić, D. M.. (2011). Thermal degradation of coordination polymer [Cd(N-Boc-gly)(2)(H2O)(2)](n). in Thermochimica Acta
Elsevier Science Bv, Amsterdam., 525(1-2), 25-30.
https://doi.org/10.1016/j.tca.2011.07.017
Šumar-Ristović M, Anđelković KK, Poleti D, Minić DM. Thermal degradation of coordination polymer [Cd(N-Boc-gly)(2)(H2O)(2)](n). in Thermochimica Acta. 2011;525(1-2):25-30.
doi:10.1016/j.tca.2011.07.017 .
Šumar-Ristović, Maja, Anđelković, Katarina K., Poleti, Dejan, Minić, Dragica M., "Thermal degradation of coordination polymer [Cd(N-Boc-gly)(2)(H2O)(2)](n)" in Thermochimica Acta, 525, no. 1-2 (2011):25-30,
https://doi.org/10.1016/j.tca.2011.07.017 . .
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