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  - Kokanov, Sanja B.
AU  - Filipović, Nenad R.
AU  - Višnjevac, Aleksandar
AU  - Nikolić, Milan
AU  - Novaković, Irena T.
AU  - Janjić, Goran
AU  - Holló, Berta Barta
AU  - Ramotowska, Sandra
AU  - Nowicka, Paulina
AU  - Makowski, Mariusz
AU  - Uğuz, Özlem
AU  - Koca, Atıf
AU  - Todorović, Tamara
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5986
AB  - Interest in Cd complexes has been growing in recent years. Cd complexes are considered a potential solution in the search for novel antibiotics that can fight antimicrobial resistance. In addition, Cd complexes draw attention to material chemistry. The main objective of this work was to prepare the first Cd(II) complexes with anionic forms of pyridine-based thiazolyl hydrazone (THs) ligands HLS2 [(E)-4-(4-methoxyphenyl)-2-(2-[pyridine-2-ylmethylene]hydrazinyl)thiazole] and HLS3 [(E)-2-(2-[pyridine-2-ylmethylene]hydrazinyl)-4-(p-tolyl)thiazole] and perform their structural and spectroscopic characterization, as well as stability in solution and upon heating. Studies related to their biological activities and possible electrochromic applications are also being conducted. Complexes [Cd(HLS2)2] (1) and [Cd(HLS3)2] (2) have been characterized by a single-crystal X-ray diffraction and computational analysis of intermolecular interactions responsible for their solid-state structures was performed. Thermal stability of 1 and 2 in the solid-state was analyzed by TGA/MS, where as their solution stability was determined by the spectrophotometric titration method. Electrochemical and in situ UV–Vis spectroelectrochemical analyses of 1 and 2 were carried out to determine redox mechanisms and the influence of the substituents and electrolytes on their redox responses. The antioxidant capacity of both complexes was tested in antioxidant assays, while their antimicrobial activity was tested against five Gram-positive and four Gram-negative bacteria, as well as against three fungi. The obtained results indicate their potent antioxidant capacity. The antimicrobial activity of investigated compounds on almost all tested bacterial strains was stronger than that of the standard antibiotic erythromycin. The results of docking studies indicate that the minor groove DNA is the possible biological target of 1 and 2.
PB  - Wiley
T2  - Applied Organometallic Chemistry
T1  - A detailed experimental and computational study of Cd complexes with pyridyl-based thiazolyl hydrazones
VL  - 37
IS  - 1
DO  - 10.1002/aoc.6942
ER  - 

@article{
author = "Kokanov, Sanja B. and Filipović, Nenad R. and Višnjevac, Aleksandar and Nikolić, Milan and Novaković, Irena T. and Janjić, Goran and Holló, Berta Barta and Ramotowska, Sandra and Nowicka, Paulina and Makowski, Mariusz and Uğuz, Özlem and Koca, Atıf and Todorović, Tamara",
year = "2023",
abstract = "Interest in Cd complexes has been growing in recent years. Cd complexes are considered a potential solution in the search for novel antibiotics that can fight antimicrobial resistance. In addition, Cd complexes draw attention to material chemistry. The main objective of this work was to prepare the first Cd(II) complexes with anionic forms of pyridine-based thiazolyl hydrazone (THs) ligands HLS2 [(E)-4-(4-methoxyphenyl)-2-(2-[pyridine-2-ylmethylene]hydrazinyl)thiazole] and HLS3 [(E)-2-(2-[pyridine-2-ylmethylene]hydrazinyl)-4-(p-tolyl)thiazole] and perform their structural and spectroscopic characterization, as well as stability in solution and upon heating. Studies related to their biological activities and possible electrochromic applications are also being conducted. Complexes [Cd(HLS2)2] (1) and [Cd(HLS3)2] (2) have been characterized by a single-crystal X-ray diffraction and computational analysis of intermolecular interactions responsible for their solid-state structures was performed. Thermal stability of 1 and 2 in the solid-state was analyzed by TGA/MS, where as their solution stability was determined by the spectrophotometric titration method. Electrochemical and in situ UV–Vis spectroelectrochemical analyses of 1 and 2 were carried out to determine redox mechanisms and the influence of the substituents and electrolytes on their redox responses. The antioxidant capacity of both complexes was tested in antioxidant assays, while their antimicrobial activity was tested against five Gram-positive and four Gram-negative bacteria, as well as against three fungi. The obtained results indicate their potent antioxidant capacity. The antimicrobial activity of investigated compounds on almost all tested bacterial strains was stronger than that of the standard antibiotic erythromycin. The results of docking studies indicate that the minor groove DNA is the possible biological target of 1 and 2.",
publisher = "Wiley",
journal = "Applied Organometallic Chemistry",
title = "A detailed experimental and computational study of Cd complexes with pyridyl-based thiazolyl hydrazones",
volume = "37",
number = "1",
doi = "10.1002/aoc.6942"
}

Kokanov, S. B., Filipović, N. R., Višnjevac, A., Nikolić, M., Novaković, I. T., Janjić, G., Holló, B. B., Ramotowska, S., Nowicka, P., Makowski, M., Uğuz, Ö., Koca, A.,& Todorović, T.. (2023). A detailed experimental and computational study of Cd complexes with pyridyl-based thiazolyl hydrazones. in Applied Organometallic Chemistry
Wiley., 37(1).
https://doi.org/10.1002/aoc.6942

Kokanov SB, Filipović NR, Višnjevac A, Nikolić M, Novaković IT, Janjić G, Holló BB, Ramotowska S, Nowicka P, Makowski M, Uğuz Ö, Koca A, Todorović T. A detailed experimental and computational study of Cd complexes with pyridyl-based thiazolyl hydrazones. in Applied Organometallic Chemistry. 2023;37(1).
doi:10.1002/aoc.6942 .

Kokanov, Sanja B., Filipović, Nenad R., Višnjevac, Aleksandar, Nikolić, Milan, Novaković, Irena T., Janjić, Goran, Holló, Berta Barta, Ramotowska, Sandra, Nowicka, Paulina, Makowski, Mariusz, Uğuz, Özlem, Koca, Atıf, Todorović, Tamara, "A detailed experimental and computational study of Cd complexes with pyridyl-based thiazolyl hydrazones" in Applied Organometallic Chemistry, 37, no. 1 (2023),
https://doi.org/10.1002/aoc.6942 . .