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  - Rodríguez-Castillo, María
AU  - Monge, Miguel
AU  - Holló, Berta Barta
AU  - Padrón, José M.
AU  - Puerta, Adrián
AU  - Sousa, Sérgio F.
AU  - Fernandes, Henrique S.
AU  - Blagojević, Vladimir
AU  - Višnjevac, Aleksandar
AU  - Olszewski, Mateusz
AU  - Maciejewska, Natalia
AU  - Araškov, Jovana
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5885
AB  - Thiazolyl-hydrazones (THs) exhibit a wide spectrum of biological activity that can be enhanced by complexation with various metal ions. Zn(II) complexes with α-pyridine-1,3-TH ligands may represent an alternative to the standard platinum-based chemotherapeutics. In addition, they show photoluminescence properties and thus can be regarded as multifunctional materials. In this study, we synthesized and characterized three neutral Zn(II) complexes (1–3) with pyridine-based TH ligands HLS1‒3 in order to investigate the influence of the ligands charge on the structure and intermolecular interactions in the solid state, and consequently photophysical properties. The deprotonation of the ligands mainly affects the relative energies of electronic levels in the complexes, compared to cationic counterparts, resulting in similar photoluminescence mechanisms and quantum yields with a small shift in emission energy. The influence of the substitution at the ligands’ periphery on the selected quantum molecular descriptors of the complexes is localized to the substitution site. Also, the substituents did not considerably influence the redox responses of the complexes. However, predominant spectral changes were observed in the course of the first reduction and oxidation processes which caused distinct spectral color changes indicating their possible functionality for electrochromic applications. In addition, complex 1 showed antiproliferative activity with GI50 values below 2 µM on all tested cancer cell lines.
PB  - Elsevier
T2  - Journal of Molecular Structure
T1  - Structural, physicochemical and anticancer study of Zn complexes with pyridyl-based thiazolyl-hydrazones
VL  - 1281
SP  - 135157
DO  - 10.1016/j.molstruc.2023.135157
ER  - 

@article{
author = "Rodríguez-Castillo, María and Monge, Miguel and Holló, Berta Barta and Padrón, José M. and Puerta, Adrián and Sousa, Sérgio F. and Fernandes, Henrique S. and Blagojević, Vladimir and Višnjevac, Aleksandar and Olszewski, Mateusz and Maciejewska, Natalia and Araškov, Jovana",
year = "2023",
abstract = "Thiazolyl-hydrazones (THs) exhibit a wide spectrum of biological activity that can be enhanced by complexation with various metal ions. Zn(II) complexes with α-pyridine-1,3-TH ligands may represent an alternative to the standard platinum-based chemotherapeutics. In addition, they show photoluminescence properties and thus can be regarded as multifunctional materials. In this study, we synthesized and characterized three neutral Zn(II) complexes (1–3) with pyridine-based TH ligands HLS1‒3 in order to investigate the influence of the ligands charge on the structure and intermolecular interactions in the solid state, and consequently photophysical properties. The deprotonation of the ligands mainly affects the relative energies of electronic levels in the complexes, compared to cationic counterparts, resulting in similar photoluminescence mechanisms and quantum yields with a small shift in emission energy. The influence of the substitution at the ligands’ periphery on the selected quantum molecular descriptors of the complexes is localized to the substitution site. Also, the substituents did not considerably influence the redox responses of the complexes. However, predominant spectral changes were observed in the course of the first reduction and oxidation processes which caused distinct spectral color changes indicating their possible functionality for electrochromic applications. In addition, complex 1 showed antiproliferative activity with GI50 values below 2 µM on all tested cancer cell lines.",
publisher = "Elsevier",
journal = "Journal of Molecular Structure",
title = "Structural, physicochemical and anticancer study of Zn complexes with pyridyl-based thiazolyl-hydrazones",
volume = "1281",
pages = "135157",
doi = "10.1016/j.molstruc.2023.135157"
}

Rodríguez-Castillo, M., Monge, M., Holló, B. B., Padrón, J. M., Puerta, A., Sousa, S. F., Fernandes, H. S., Blagojević, V., Višnjevac, A., Olszewski, M., Maciejewska, N.,& Araškov, J.. (2023). Structural, physicochemical and anticancer study of Zn complexes with pyridyl-based thiazolyl-hydrazones. in Journal of Molecular Structure
Elsevier., 1281, 135157.
https://doi.org/10.1016/j.molstruc.2023.135157

Rodríguez-Castillo M, Monge M, Holló BB, Padrón JM, Puerta A, Sousa SF, Fernandes HS, Blagojević V, Višnjevac A, Olszewski M, Maciejewska N, Araškov J. Structural, physicochemical and anticancer study of Zn complexes with pyridyl-based thiazolyl-hydrazones. in Journal of Molecular Structure. 2023;1281:135157.
doi:10.1016/j.molstruc.2023.135157 .

Rodríguez-Castillo, María, Monge, Miguel, Holló, Berta Barta, Padrón, José M., Puerta, Adrián, Sousa, Sérgio F., Fernandes, Henrique S., Blagojević, Vladimir, Višnjevac, Aleksandar, Olszewski, Mateusz, Maciejewska, Natalia, Araškov, Jovana, "Structural, physicochemical and anticancer study of Zn complexes with pyridyl-based thiazolyl-hydrazones" in Journal of Molecular Structure, 1281 (2023):135157,
https://doi.org/10.1016/j.molstruc.2023.135157 . .

TY  - JOUR
AU  - Marković, Sanja B.
AU  - Maciejewska, Natalia
AU  - Olszewski, Mateusz
AU  - Višnjevac, Aleksandar
AU  - Puerta, Adrián
AU  - Padrón, José M.
AU  - Novaković, Irena T.
AU  - Kojić, Snežana
AU  - Fernandes, Henrique S.
AU  - Sousa, Sérgio F.
AU  - Ramotowska, Sandra
AU  - Chylewska, Agnieszka
AU  - Makowski, Mariusz
AU  - Todorović, Tamara
AU  - Filipović, Nenad R.
PY  - 2022
UR  - https://www.sciencedirect.com/science/article/pii/S0223523422003518
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5209
AB  - The biological activity of Cd compounds has been investigated scarce since Cd has been recognized as a human carcinogen. However, the toxicity of cadmium is comparable to the toxicity of noble metals such as Pt and Pd. The paradigm of metal toxicity has been challenged suggesting that metal toxicity is not a constant property, yet it depends on many factors like the presence of appropriate ligands. Studies on anticancer activity of cadmium complexes showed that the complexation of various ligands resulted in complexes that showed better activities than approved drugs. In the present study, cadmium complexes with biologically potent thiazolyl/selenazoyl-hydrazone ligands have been prepared, and tested for their activity against different types of tumor cell models. The complexation of ligands with Cd(II) resulted in a synergistic effect. The antiproliferative activity study revealed that all complexes are more active compared to 5-fluorouracil and cisplatin. The mechanism of tumor cell growth inhibition reveal that selenium-based compounds induce cell death in T-47D (gland carcinoma) cells through apoptosis via caspase-3/7 activation. Additionally, their pro-apoptotic effect was stronger compared to etoposide and cisplatin. Nuclease activity, detected by gel electrophoresis, may be the possible mechanism of anticancer action of investigated complexes.
PB  - Elsevier
T2  - European Journal of Medicinal Chemistry
T1  - Study of the anticancer potential of Cd complexes of selenazoyl-hydrazones and their sulfur isosters
VL  - 238
SP  - 114449
DO  - 10.1016/j.ejmech.2022.114449
ER  - 

@article{
author = "Marković, Sanja B. and Maciejewska, Natalia and Olszewski, Mateusz and Višnjevac, Aleksandar and Puerta, Adrián and Padrón, José M. and Novaković, Irena T. and Kojić, Snežana and Fernandes, Henrique S. and Sousa, Sérgio F. and Ramotowska, Sandra and Chylewska, Agnieszka and Makowski, Mariusz and Todorović, Tamara and Filipović, Nenad R.",
year = "2022",
abstract = "The biological activity of Cd compounds has been investigated scarce since Cd has been recognized as a human carcinogen. However, the toxicity of cadmium is comparable to the toxicity of noble metals such as Pt and Pd. The paradigm of metal toxicity has been challenged suggesting that metal toxicity is not a constant property, yet it depends on many factors like the presence of appropriate ligands. Studies on anticancer activity of cadmium complexes showed that the complexation of various ligands resulted in complexes that showed better activities than approved drugs. In the present study, cadmium complexes with biologically potent thiazolyl/selenazoyl-hydrazone ligands have been prepared, and tested for their activity against different types of tumor cell models. The complexation of ligands with Cd(II) resulted in a synergistic effect. The antiproliferative activity study revealed that all complexes are more active compared to 5-fluorouracil and cisplatin. The mechanism of tumor cell growth inhibition reveal that selenium-based compounds induce cell death in T-47D (gland carcinoma) cells through apoptosis via caspase-3/7 activation. Additionally, their pro-apoptotic effect was stronger compared to etoposide and cisplatin. Nuclease activity, detected by gel electrophoresis, may be the possible mechanism of anticancer action of investigated complexes.",
publisher = "Elsevier",
journal = "European Journal of Medicinal Chemistry",
title = "Study of the anticancer potential of Cd complexes of selenazoyl-hydrazones and their sulfur isosters",
volume = "238",
pages = "114449",
doi = "10.1016/j.ejmech.2022.114449"
}

Marković, S. B., Maciejewska, N., Olszewski, M., Višnjevac, A., Puerta, A., Padrón, J. M., Novaković, I. T., Kojić, S., Fernandes, H. S., Sousa, S. F., Ramotowska, S., Chylewska, A., Makowski, M., Todorović, T.,& Filipović, N. R.. (2022). Study of the anticancer potential of Cd complexes of selenazoyl-hydrazones and their sulfur isosters. in European Journal of Medicinal Chemistry
Elsevier., 238, 114449.
https://doi.org/10.1016/j.ejmech.2022.114449

Marković SB, Maciejewska N, Olszewski M, Višnjevac A, Puerta A, Padrón JM, Novaković IT, Kojić S, Fernandes HS, Sousa SF, Ramotowska S, Chylewska A, Makowski M, Todorović T, Filipović NR. Study of the anticancer potential of Cd complexes of selenazoyl-hydrazones and their sulfur isosters. in European Journal of Medicinal Chemistry. 2022;238:114449.
doi:10.1016/j.ejmech.2022.114449 .

Marković, Sanja B., Maciejewska, Natalia, Olszewski, Mateusz, Višnjevac, Aleksandar, Puerta, Adrián, Padrón, José M., Novaković, Irena T., Kojić, Snežana, Fernandes, Henrique S., Sousa, Sérgio F., Ramotowska, Sandra, Chylewska, Agnieszka, Makowski, Mariusz, Todorović, Tamara, Filipović, Nenad R., "Study of the anticancer potential of Cd complexes of selenazoyl-hydrazones and their sulfur isosters" in European Journal of Medicinal Chemistry, 238 (2022):114449,
https://doi.org/10.1016/j.ejmech.2022.114449 . .