Quinoline-based thiazolyl-hydrazones target cancer cells through autophagy inhibition
Само за регистроване кориснике
2024
Аутори
Ćurčić, VladimirOlszewski, Mateusz
Maciejewska, Natalia
Višnjevac, Aleksandar
Srdić-Rajić, Tatjana
Dobričić, Vladimir
García-Sosa, Alfonso T.
Kokanov, Sanja B.
Araškov, Jovana B.
Silvestri, Romano
Schüle, Roland
Jung, Manfred
Nikolić, Milan
Filipović, Nenad R.
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
DNA damage / anticancer activity / hydrazonyl-thiazoles / lysosomes targeting / quinoline derivativesИзвор:
Archiv der Pharmazie, 2024, 357, 2, 2300426-Издавач:
- John Wiley and Sons Inc
Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200168 (Универзитет у Београду, Хемијски факултет) (RS-MESTD-inst-2020-200168)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200161 (Универзитет у Београду, Фармацеутски факултет) (RS-MESTD-inst-2020-200161)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200116 (Универзитет у Београду, Пољопривредни факултет) (RS-MESTD-inst-2020-200116)
- AIRC IG 2020, code no. 24703. A.T.G.S.
- The Estonian Research Council (PRG1509)
- The Deutsche Forschungsgemeinschaft (DFG, German Research Founda- tion): SFB 992 (Project‐ID: 192904750)
- CIBBS Germany's Excel- lence Strategy–EXC‐2189–Project ID: 390939984 to M.J.
DOI: 10.1002/ardp.202300426
ISSN: 0365-6233
PubMed: 37991233
WoS: 001108118000001
Scopus: 2-s2.0-85177552592
Институција/група
PharmacyTY - 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 B. AU - Silvestri, Romano AU - Schüle, Roland AU - Jung, Manfred AU - Nikolić, Milan AU - Filipović, Nenad R. PY - 2024 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5298 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 T1 - Quinoline-based thiazolyl-hydrazones target cancer cells through autophagy inhibition VL - 357 IS - 2 SP - 2300426 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 B. and Silvestri, Romano and Schüle, Roland and Jung, Manfred and Nikolić, Milan and Filipović, Nenad R.", year = "2024", 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", title = "Quinoline-based thiazolyl-hydrazones target cancer cells through autophagy inhibition", volume = "357", number = "2", pages = "2300426", 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. B., Silvestri, R., Schüle, R., Jung, M., Nikolić, M.,& Filipović, N. R.. (2024). Quinoline-based thiazolyl-hydrazones target cancer cells through autophagy inhibition. in Archiv der Pharmazie John Wiley and Sons Inc., 357(2), 2300426. 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 JB, Silvestri R, Schüle R, Jung M, Nikolić M, Filipović NR. Quinoline-based thiazolyl-hydrazones target cancer cells through autophagy inhibition. in Archiv der Pharmazie. 2024;357(2):2300426. 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 B., 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, 357, no. 2 (2024):2300426, https://doi.org/10.1002/ardp.202300426 . .