TY  - JOUR
AU  - Filipović, Nenad R.
AU  - Bjelogrlić, Snežana
AU  - Portalone, Gustavo
AU  - Pelliccia, Sveva
AU  - Silvestri, Romano
AU  - Klisuric, Olivera
AU  - Senćanski, Milan V.
AU  - Stanković, Dalibor M.
AU  - Todorović, Tamara R.
AU  - Muller, Christian D.
PY  - 2016
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1206
AB  - 8-Quinolinecarboxaldehyde selenosemicarbazone (H8qasesc) and its octahedral Co(III) complex were characterized by single crystal X-ray diffraction analysis, spectroscopy methods and cyclic voltammetry. The antineoplastic activity of the ligand and the complex has been assessed on an acute monocytic leukemia cell line (THP-1) and AsPC-1 cancer stem cell (CSC) line derived from a patient suffering from pancreatic adenocarcinoma, with cisplatin (CDDP) as a reference compound. Evaluation involved determination of pro-apoptotic activity, changes in cell cycle distribution, the role of caspase activation in the process of cell death, and the ability of the investigated compounds to challenge reprogramming of the CSC phenotype. Compared to CDDP, treatment with H8qasesc induced a higher apoptotic response in both investigated cell lines. Apoptosis triggered by H8qasesc was highly caspase-dependent but did not include activation of either caspase-8 or -9. According to cell cycle changes H8qasesc delayed the transition of cells during DNA replication but in a manner different from that of CDDP. The ligand did not show nuclease activity on pUC19 plasmid, while docking studies disclosed that it does not have intercalating properties. Treatment of THP-1 cells with the Co(III) complex resulted in a strong toxic response, whereas cell death in the treated AsPC-1 line was not achieved for 24 h. Additionally, the complex concentration-dependently digested plasmid DNA which might be the cause of its cytotoxic activity. Finally, H8qasesc successfully initiated reprogramming of the CSC phenotype in the AsPC-1 cell line.
T2  - MedChemComm
T1  - Pro-apoptotic and pro-differentiation induction by 8-quinolinecarboxaldehyde selenosemicarbazone and its Co(III) complex in human cancer cell lines
VL  - 7
IS  - 8
SP  - 1604
EP  - 1616
DO  - 10.1039/c6md00199h
ER  - 

@article{
author = "Filipović, Nenad R. and Bjelogrlić, Snežana and Portalone, Gustavo and Pelliccia, Sveva and Silvestri, Romano and Klisuric, Olivera and Senćanski, Milan V. and Stanković, Dalibor M. and Todorović, Tamara R. and Muller, Christian D.",
year = "2016",
abstract = "8-Quinolinecarboxaldehyde selenosemicarbazone (H8qasesc) and its octahedral Co(III) complex were characterized by single crystal X-ray diffraction analysis, spectroscopy methods and cyclic voltammetry. The antineoplastic activity of the ligand and the complex has been assessed on an acute monocytic leukemia cell line (THP-1) and AsPC-1 cancer stem cell (CSC) line derived from a patient suffering from pancreatic adenocarcinoma, with cisplatin (CDDP) as a reference compound. Evaluation involved determination of pro-apoptotic activity, changes in cell cycle distribution, the role of caspase activation in the process of cell death, and the ability of the investigated compounds to challenge reprogramming of the CSC phenotype. Compared to CDDP, treatment with H8qasesc induced a higher apoptotic response in both investigated cell lines. Apoptosis triggered by H8qasesc was highly caspase-dependent but did not include activation of either caspase-8 or -9. According to cell cycle changes H8qasesc delayed the transition of cells during DNA replication but in a manner different from that of CDDP. The ligand did not show nuclease activity on pUC19 plasmid, while docking studies disclosed that it does not have intercalating properties. Treatment of THP-1 cells with the Co(III) complex resulted in a strong toxic response, whereas cell death in the treated AsPC-1 line was not achieved for 24 h. Additionally, the complex concentration-dependently digested plasmid DNA which might be the cause of its cytotoxic activity. Finally, H8qasesc successfully initiated reprogramming of the CSC phenotype in the AsPC-1 cell line.",
journal = "MedChemComm",
title = "Pro-apoptotic and pro-differentiation induction by 8-quinolinecarboxaldehyde selenosemicarbazone and its Co(III) complex in human cancer cell lines",
volume = "7",
number = "8",
pages = "1604-1616",
doi = "10.1039/c6md00199h"
}

Filipović, N. R., Bjelogrlić, S., Portalone, G., Pelliccia, S., Silvestri, R., Klisuric, O., Senćanski, M. V., Stanković, D. M., Todorović, T. R.,& Muller, C. D.. (2016). Pro-apoptotic and pro-differentiation induction by 8-quinolinecarboxaldehyde selenosemicarbazone and its Co(III) complex in human cancer cell lines. in MedChemComm, 7(8), 1604-1616.
https://doi.org/10.1039/c6md00199h

Filipović NR, Bjelogrlić S, Portalone G, Pelliccia S, Silvestri R, Klisuric O, Senćanski MV, Stanković DM, Todorović TR, Muller CD. Pro-apoptotic and pro-differentiation induction by 8-quinolinecarboxaldehyde selenosemicarbazone and its Co(III) complex in human cancer cell lines. in MedChemComm. 2016;7(8):1604-1616.
doi:10.1039/c6md00199h .

Filipović, Nenad R., Bjelogrlić, Snežana, Portalone, Gustavo, Pelliccia, Sveva, Silvestri, Romano, Klisuric, Olivera, Senćanski, Milan V., Stanković, Dalibor M., Todorović, Tamara R., Muller, Christian D., "Pro-apoptotic and pro-differentiation induction by 8-quinolinecarboxaldehyde selenosemicarbazone and its Co(III) complex in human cancer cell lines" in MedChemComm, 7, no. 8 (2016):1604-1616,
https://doi.org/10.1039/c6md00199h . .

TY  - JOUR
AU  - Filipović, Nenad R.
AU  - Bjelogrlić, Snežana
AU  - Todorović, Tamara R.
AU  - Blagojević, Vladimir A.
AU  - Muller, Christian D.
AU  - Marinković, Aleksandar D.
AU  - Vujčić, Miroslava T.
AU  - Janović, Barbara S.
AU  - Malešević, Aleksandar S.
AU  - Begović, Nebojša
AU  - Senćanski, Milan V.
AU  - Minić, Dragica M.
PY  - 2016
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1331
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.
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
VL  - 6
IS  - 110
SP  - 108726
EP  - 108740
DO  - 10.1039/c6ra24604d
ER  - 

@article{
author = "Filipović, Nenad R. and Bjelogrlić, Snežana and Todorović, Tamara R. and Blagojević, Vladimir A. and Muller, Christian D. and Marinković, Aleksandar D. and Vujčić, Miroslava T. and Janović, Barbara S. and Malešević, Aleksandar S. 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.",
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",
volume = "6",
number = "110",
pages = "108726-108740",
doi = "10.1039/c6ra24604d"
}

Filipović, N. R., Bjelogrlić, S., Todorović, T. R., Blagojević, V. A., Muller, C. D., Marinković, A. D., Vujčić, M. T., Janović, B. S., Malešević, A. S., 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, 6(110), 108726-108740.
https://doi.org/10.1039/c6ra24604d

Filipović NR, Bjelogrlić S, Todorović TR, Blagojević VA, Muller CD, Marinković AD, Vujčić MT, Janović BS, Malešević AS, 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, Todorović, Tamara R., Blagojević, Vladimir A., Muller, Christian D., Marinković, Aleksandar D., Vujčić, Miroslava T., Janović, Barbara S., Malešević, Aleksandar S., 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 . .

TY  - JOUR
AU  - Filipović, Nenad R.
AU  - Bjelogrlić, Snežana
AU  - Marinković, Aleksandar D.
AU  - Verbić, Tatjana Z.
AU  - Cvijetić, Ilija N.
AU  - Senćanski, Milan V.
AU  - Rodić, Marko
AU  - Vujčić, Miroslava T.
AU  - Sladić, Dušan M.
AU  - Striković, Zlatko
AU  - Todorović, Tamara R.
AU  - Muller, Christian D.
PY  - 2015
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/809
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.
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
VL  - 5
IS  - 115
SP  - 95191
EP  - 95211
DO  - 10.1039/c5ra19849f
ER  - 

@article{
author = "Filipović, Nenad R. and Bjelogrlić, Snežana and Marinković, Aleksandar D. and Verbić, Tatjana Z. and Cvijetić, Ilija N. and Senćanski, Milan V. and Rodić, Marko and Vujčić, Miroslava T. and Sladić, Dušan M. and Striković, Zlatko and Todorović, Tamara R. 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.",
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",
volume = "5",
number = "115",
pages = "95191-95211",
doi = "10.1039/c5ra19849f"
}

Filipović, N. R., Bjelogrlić, S., Marinković, A. D., Verbić, T. Z., Cvijetić, I. N., Senćanski, M. V., Rodić, M., Vujčić, M. T., Sladić, D. M., Striković, Z., Todorović, T. R.,& 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, 5(115), 95191-95211.
https://doi.org/10.1039/c5ra19849f

Filipović NR, Bjelogrlić S, Marinković AD, Verbić TZ, Cvijetić IN, Senćanski MV, Rodić M, Vujčić MT, Sladić DM, Striković Z, Todorović TR, 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, Marinković, Aleksandar D., Verbić, Tatjana Z., Cvijetić, Ilija N., Senćanski, Milan V., Rodić, Marko, Vujčić, Miroslava T., Sladić, Dušan M., Striković, Zlatko, Todorović, Tamara R., 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 . .

TY  - JOUR
AU  - Filipović, Nenad R.
AU  - Borrmann, Horst
AU  - Todorović, Tamara
AU  - Borna, Marija
AU  - Spasojević, Vojislav
AU  - Sladić, Dušan M.
AU  - Novaković, Irena T.
AU  - Anđelković, Katarina
PY  - 2009
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/3680
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 [CuCl(2)L] 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 [Cu(2)Cl(4)L(2)] 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. (c) 2008 Elsevier B.V. All rights reserved.
T2  - Inorganica Chimica Acta
T1  - Copper(II) complexes of N-heteroaromatic hydrazones: Synthesis, X-ray structure, magnetic behavior, and antibacterial activity
VL  - 362
IS  - 6
SP  - 1996
EP  - 2000
DO  - 10.1016/j.ica.2008.09.019
ER  - 

@article{
author = "Filipović, Nenad R. and Borrmann, Horst and Todorović, Tamara and Borna, Marija and Spasojević, Vojislav and Sladić, Dušan M. and Novaković, Irena T. and Anđelković, 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 [CuCl(2)L] 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 [Cu(2)Cl(4)L(2)] 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. (c) 2008 Elsevier B.V. All rights reserved.",
journal = "Inorganica Chimica Acta",
title = "Copper(II) complexes of N-heteroaromatic hydrazones: Synthesis, X-ray structure, magnetic behavior, and antibacterial activity",
volume = "362",
number = "6",
pages = "1996-2000",
doi = "10.1016/j.ica.2008.09.019"
}

Filipović, N. R., Borrmann, H., Todorović, T., Borna, M., Spasojević, V., Sladić, D. M., Novaković, I. T.,& Anđelković, K.. (2009). Copper(II) complexes of N-heteroaromatic hydrazones: Synthesis, X-ray structure, magnetic behavior, and antibacterial activity. in Inorganica Chimica Acta, 362(6), 1996-2000.
https://doi.org/10.1016/j.ica.2008.09.019

Filipović NR, Borrmann H, Todorović T, Borna M, Spasojević V, Sladić DM, Novaković IT, Anđelković 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 R., Borrmann, Horst, Todorović, Tamara, Borna, Marija, Spasojević, Vojislav, Sladić, Dušan M., Novaković, Irena T., Anđelković, 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 . .