TY  - JOUR
AU  - Ćurčić, Vladimir
AU  - Olszewski, Mateusz
AU  - Maciejewska, Natalia
AU  - Višnjevac, Aleksandar
AU  - Srdić-Rajić, Tatjana
AU  - Dobričić, Vladimir
AU  - García-Sosa, Alfonso T.
AU  - Kokanov, Sanja B.
AU  - Araškov, Jovana
AU  - Silvestri, Romano
AU  - Schüle, Roland
AU  - Jung, Manfred
AU  - Nikolić, Milan
AU  - Filipović, Nenad R.
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6392
AB  - Heterocyclic pharmacophores such as thiazole and quinoline rings have a significant role in medicinal chemistry. They are considered privileged structures since they constitute several Food and Drug Administration (FDA)-approved drugs for cancer treatment. Herein, we report the synthesis, in silico evaluation of the ADMET profiles, and in vitro investigation of the anticancer activity of a series of novel thiazolyl-hydrazones based on the 8-quinoline (1a–c), 2-quinoline (2a–c), and 8-hydroxy-2-quinolyl moiety (3a–c). The panel of several human cancer cell lines and the nontumorigenic human embryonic kidney cell line HEK-293 were used to evaluate the compound-mediated in vitro anticancer activities, leading to [2-(2-(quinolyl-8-ol-2-ylmethylene)hydrazinyl)]-4-(4-methoxyphenyl)-1,3-thiazole (3c) as the most promising compound. The study revealed that 3c blocks the cell-cycle progression of a human colon cancer cell line (HCT-116) in the S phase and induces DNA double-strand breaks. Also, our findings demonstrate that 3c accumulates in lysosomes, ultimately leading to the cell death of the hepatocellular carcinoma cell line (Hep-G2) and HCT-116 cells, by the mechanism of autophagy inhibition.
PB  - John Wiley and Sons Inc
T2  - Archiv der Pharmazie
T2  - Archiv der Pharmazie
T1  - Quinoline-based thiazolyl-hydrazones target cancer cells through autophagy inhibition
VL  - n/a
IS  - n/a
SP  - e2300426
DO  - 10.1002/ardp.202300426
ER  - 

@article{
author = "Ćurčić, Vladimir and Olszewski, Mateusz and Maciejewska, Natalia and Višnjevac, Aleksandar and Srdić-Rajić, Tatjana and Dobričić, Vladimir and García-Sosa, Alfonso T. and Kokanov, Sanja B. and Araškov, Jovana and Silvestri, Romano and Schüle, Roland and Jung, Manfred and Nikolić, Milan and Filipović, Nenad R.",
abstract = "Heterocyclic pharmacophores such as thiazole and quinoline rings have a significant role in medicinal chemistry. They are considered privileged structures since they constitute several Food and Drug Administration (FDA)-approved drugs for cancer treatment. Herein, we report the synthesis, in silico evaluation of the ADMET profiles, and in vitro investigation of the anticancer activity of a series of novel thiazolyl-hydrazones based on the 8-quinoline (1a–c), 2-quinoline (2a–c), and 8-hydroxy-2-quinolyl moiety (3a–c). The panel of several human cancer cell lines and the nontumorigenic human embryonic kidney cell line HEK-293 were used to evaluate the compound-mediated in vitro anticancer activities, leading to [2-(2-(quinolyl-8-ol-2-ylmethylene)hydrazinyl)]-4-(4-methoxyphenyl)-1,3-thiazole (3c) as the most promising compound. The study revealed that 3c blocks the cell-cycle progression of a human colon cancer cell line (HCT-116) in the S phase and induces DNA double-strand breaks. Also, our findings demonstrate that 3c accumulates in lysosomes, ultimately leading to the cell death of the hepatocellular carcinoma cell line (Hep-G2) and HCT-116 cells, by the mechanism of autophagy inhibition.",
publisher = "John Wiley and Sons Inc",
journal = "Archiv der Pharmazie, Archiv der Pharmazie",
title = "Quinoline-based thiazolyl-hydrazones target cancer cells through autophagy inhibition",
volume = "n/a",
number = "n/a",
pages = "e2300426",
doi = "10.1002/ardp.202300426"
}

Ćurčić, V., Olszewski, M., Maciejewska, N., Višnjevac, A., Srdić-Rajić, T., Dobričić, V., García-Sosa, A. T., Kokanov, S. B., Araškov, J., Silvestri, R., Schüle, R., Jung, M., Nikolić, M.,& Filipović, N. R..Quinoline-based thiazolyl-hydrazones target cancer cells through autophagy inhibition. in Archiv der Pharmazie
John Wiley and Sons Inc., n/a(n/a), e2300426.
https://doi.org/10.1002/ardp.202300426

Ćurčić V, Olszewski M, Maciejewska N, Višnjevac A, Srdić-Rajić T, Dobričić V, García-Sosa AT, Kokanov SB, Araškov J, Silvestri R, Schüle R, Jung M, Nikolić M, Filipović NR. Quinoline-based thiazolyl-hydrazones target cancer cells through autophagy inhibition. in Archiv der Pharmazie.n/a(n/a):e2300426.
doi:10.1002/ardp.202300426 .

Ćurčić, Vladimir, Olszewski, Mateusz, Maciejewska, Natalia, Višnjevac, Aleksandar, Srdić-Rajić, Tatjana, Dobričić, Vladimir, García-Sosa, Alfonso T., Kokanov, Sanja B., Araškov, Jovana, Silvestri, Romano, Schüle, Roland, Jung, Manfred, Nikolić, Milan, Filipović, Nenad R., "Quinoline-based thiazolyl-hydrazones target cancer cells through autophagy inhibition" in Archiv der Pharmazie, n/a, no. n/a:e2300426,
https://doi.org/10.1002/ardp.202300426 . .

TY  - JOUR
AU  - Filipović, Nenad R.
AU  - Bjelogrlić, Snežana K.
AU  - Portalone, Gustavo
AU  - Pelliccia, Sveva
AU  - Silvestri, Romano
AU  - Klisurić, Olivera
AU  - Senćanski, Milan
AU  - Stanković, Dalibor
AU  - Todorović, Tamara
AU  - Muller, Christian D.
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2293
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.
PB  - Royal Soc Chemistry, Cambridge
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 K. and Portalone, Gustavo and Pelliccia, Sveva and Silvestri, Romano and Klisurić, Olivera and Senćanski, Milan and Stanković, Dalibor and Todorović, Tamara 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.",
publisher = "Royal Soc Chemistry, Cambridge",
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. K., Portalone, G., Pelliccia, S., Silvestri, R., Klisurić, O., Senćanski, M., Stanković, D., Todorović, T.,& 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
Royal Soc Chemistry, Cambridge., 7(8), 1604-1616.
https://doi.org/10.1039/c6md00199h

Filipović NR, Bjelogrlić SK, Portalone G, Pelliccia S, Silvestri R, Klisurić O, Senćanski M, Stanković D, Todorović T, 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 K., Portalone, Gustavo, Pelliccia, Sveva, Silvestri, Romano, Klisurić, Olivera, Senćanski, Milan, Stanković, Dalibor, Todorović, Tamara, 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 K.
AU  - Portalone, Gustavo
AU  - Pelliccia, Sveva
AU  - Silvestri, Romano
AU  - Klisurić, Olivera
AU  - Senćanski, Milan
AU  - Stanković, Dalibor
AU  - Todorović, Tamara
AU  - Muller, Christian D.
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3598
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.
PB  - Royal Soc Chemistry, Cambridge
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 K. and Portalone, Gustavo and Pelliccia, Sveva and Silvestri, Romano and Klisurić, Olivera and Senćanski, Milan and Stanković, Dalibor and Todorović, Tamara 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.",
publisher = "Royal Soc Chemistry, Cambridge",
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. K., Portalone, G., Pelliccia, S., Silvestri, R., Klisurić, O., Senćanski, M., Stanković, D., Todorović, T.,& 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
Royal Soc Chemistry, Cambridge., 7(8), 1604-1616.
https://doi.org/10.1039/c6md00199h

Filipović NR, Bjelogrlić SK, Portalone G, Pelliccia S, Silvestri R, Klisurić O, Senćanski M, Stanković D, Todorović T, 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 K., Portalone, Gustavo, Pelliccia, Sveva, Silvestri, Romano, Klisurić, Olivera, Senćanski, Milan, Stanković, Dalibor, Todorović, Tamara, 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  - DATA
AU  - Filipović, Nenad R.
AU  - Bjelogrlić, Snežana K.
AU  - Portalone, Gustavo
AU  - Pelliccia, Sveva
AU  - Silvestri, Romano
AU  - Klisurić, Olivera
AU  - Senćanski, Milan
AU  - Stanković, Dalibor
AU  - Todorović, Tamara
AU  - Muller, Christian D.
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3599
PB  - Royal Soc Chemistry, Cambridge
T2  - MedChemComm
T1  - Supplementary data for the article: Filipović, N. R.; Bjelogrlić, S.; Portalone, G.; Pelliccia, S.; Silvestri, R.; Klisurić, O.; Senćanski, M.; Stanković, D.; Todorović, T. R.; Muller, C. D. Pro-Apoptotic and pro-Differentiation Induction by 8-Quinolinecarboxaldehyde Selenosemicarbazone and Its Co(III) Complex in Human Cancer Cell Lines. MedChemComm 2016, 7 (8), 1604–1616. https://doi.org/10.1039/c6md00199h
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3599
ER  - 

@misc{
author = "Filipović, Nenad R. and Bjelogrlić, Snežana K. and Portalone, Gustavo and Pelliccia, Sveva and Silvestri, Romano and Klisurić, Olivera and Senćanski, Milan and Stanković, Dalibor and Todorović, Tamara and Muller, Christian D.",
year = "2016",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "MedChemComm",
title = "Supplementary data for the article: Filipović, N. R.; Bjelogrlić, S.; Portalone, G.; Pelliccia, S.; Silvestri, R.; Klisurić, O.; Senćanski, M.; Stanković, D.; Todorović, T. R.; Muller, C. D. Pro-Apoptotic and pro-Differentiation Induction by 8-Quinolinecarboxaldehyde Selenosemicarbazone and Its Co(III) Complex in Human Cancer Cell Lines. MedChemComm 2016, 7 (8), 1604–1616. https://doi.org/10.1039/c6md00199h",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3599"
}

Filipović, N. R., Bjelogrlić, S. K., Portalone, G., Pelliccia, S., Silvestri, R., Klisurić, O., Senćanski, M., Stanković, D., Todorović, T.,& Muller, C. D.. (2016). Supplementary data for the article: Filipović, N. R.; Bjelogrlić, S.; Portalone, G.; Pelliccia, S.; Silvestri, R.; Klisurić, O.; Senćanski, M.; Stanković, D.; Todorović, T. R.; Muller, C. D. Pro-Apoptotic and pro-Differentiation Induction by 8-Quinolinecarboxaldehyde Selenosemicarbazone and Its Co(III) Complex in Human Cancer Cell Lines. MedChemComm 2016, 7 (8), 1604–1616. https://doi.org/10.1039/c6md00199h. in MedChemComm
Royal Soc Chemistry, Cambridge..
https://hdl.handle.net/21.15107/rcub_cherry_3599

Filipović NR, Bjelogrlić SK, Portalone G, Pelliccia S, Silvestri R, Klisurić O, Senćanski M, Stanković D, Todorović T, Muller CD. Supplementary data for the article: Filipović, N. R.; Bjelogrlić, S.; Portalone, G.; Pelliccia, S.; Silvestri, R.; Klisurić, O.; Senćanski, M.; Stanković, D.; Todorović, T. R.; Muller, C. D. Pro-Apoptotic and pro-Differentiation Induction by 8-Quinolinecarboxaldehyde Selenosemicarbazone and Its Co(III) Complex in Human Cancer Cell Lines. MedChemComm 2016, 7 (8), 1604–1616. https://doi.org/10.1039/c6md00199h. in MedChemComm. 2016;.
https://hdl.handle.net/21.15107/rcub_cherry_3599 .

Filipović, Nenad R., Bjelogrlić, Snežana K., Portalone, Gustavo, Pelliccia, Sveva, Silvestri, Romano, Klisurić, Olivera, Senćanski, Milan, Stanković, Dalibor, Todorović, Tamara, Muller, Christian D., "Supplementary data for the article: Filipović, N. R.; Bjelogrlić, S.; Portalone, G.; Pelliccia, S.; Silvestri, R.; Klisurić, O.; Senćanski, M.; Stanković, D.; Todorović, T. R.; Muller, C. D. Pro-Apoptotic and pro-Differentiation Induction by 8-Quinolinecarboxaldehyde Selenosemicarbazone and Its Co(III) Complex in Human Cancer Cell Lines. MedChemComm 2016, 7 (8), 1604–1616. https://doi.org/10.1039/c6md00199h" in MedChemComm (2016),
https://hdl.handle.net/21.15107/rcub_cherry_3599 .