Novel thiazole/ethyl thiazole carboxylate-acetamide derivatives and their cytotoxic effect evaluation

Yıl 2024, Cilt: 17 Sayı: 2, 104 – 116, 30.06.2024

Asaf Evrim Evren , Sam Dawbaa , Demokrat Nuha , Aybüke Züleyha Kaya , Zerrin Canturk , Leyla Yurttaş

https://doi.org/10.30607/kvj.1430771

Öz

In this study, the main goal is to determine the anticancer compound(s) that can be used against A549 non-small lung epithelial carcinoma, Caco-2 colon carcinoma, and SHSY-5Y neuroblastoma cells with high selectivity. For this purpose, our study group synthesized two similar acetamide series: four compounds (3a–3d), including thiazole, and four compounds (3e–3h), including ethyl (4-methyl-thiazol-5-yl)carboxylate. The structural analyses of eight compounds were identified by HRMS, 1H-NMR, and 13C-NMR. After approving the purity, their anticancer profiles were evaluated against above cancer cells, and the cytotoxicity effect was also tested against NIH/3T3 fibroblast cells. Meanwhile, ADME and DFT calculations indicated that compounds have good ADME profiles and chemical stability. Among the targeted compounds, compound 3g exhibits greater stability. In chemical systems, stability is important because it represents the energy balance within a molecule. The results showed that compounds have significant impact on SHSY-5Y cells with higher selectivity than other cells. The combination of ester groups on thiazole and thiazoline (compound 3g) was found to be significantly more effective than doxorubicin and highly selective on SHSY-5Y cells than healthy cells. Besides that, combination of thiazole and triazole (3d and 3h) decreased antiproliferative activity in three cancer cells while increasing cytotoxicity in healthy cells. This study suggests that future perspectives in studies regarding the treatments of neuroblastoma and its related diseases of ethyl 2-acetamido-4-methylthiazole-5-carboxylate and thiazoline combination are encouraging.

Anahtar Kelimeler

Thiazole, Ethyl carboxylate, DFT, Anticancer activity, SHSY-5Y

Kaynakça

• Ahmed, K., Matsuya, Y., Nemoto, H., Zaidi, S.F., Sugiyama, T., Yoshihisa, Y., Shimizu, T., Kondo, T. (2009). Mechanism of apoptosis induced by a newly synthesized derivative of macrosphelides with a thiazole side chain. Chem Biol Interact, 177 (3), 218-226. 10.1016/j.cbi.2008.10.030
• Altintop, M.D., Kaplancikli, Z.A., Ciftci, G.A., Demirel, R. (2014). Synthesis and biological evaluation of thiazoline derivatives as new antimicrobial and anticancer agents. Eur. J. Med. Chem., 74, 264-277. 10.1016/j.ejmech.2013.12.060
• Bhagat, D.S., Chawla, P.A., Gurnule, W.B., Shejul, S.K., Bumbrah, G.S. (2021). An Insight into Synthesis and Anticancer Potential of Thiazole and 4-thiazolidinone Containing Motifs. Current Organic Chemistry, 25 (7), 819-841. 10.2174/1385272825999210101234704
• Bhat, U.G., Halasi, M., Gartel, A.L. (2009). Thiazole antibiotics target FoxM1 and induce apoptosis in human cancer cells. PLoS One, 4 (5), e5592. 10.1371/journal.pone.0005592
• Catarzi, D., Varano, F., Vigiani, E., Lambertucci, C., Spinaci, A., Volpini, R., Colotta, V. (2022). Casein Kinase 1delta Inhibitors as Promising Therapeutic Agents for Neurodegenerative Disorders. Curr Med Chem, 29 (27), 4698-4737. 10.2174/0929867329666220301115124
• Cavalier, H., Trasande, L., Porta, M. (2023). Exposures to pesticides and risk of cancer: Evaluation of recent epidemiological evidence in humans and paths forward. International Journal of Cancer, 152 (5), 879-912.
• Cortes, A.J. (2019). Molecular biology of cancer: similarities between humans and animals. Revista Veterinaria y Zootecnia (On Line), 13 (2), 81-95.
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Yeni tiyazol/etil tiyazol karboksilat-asetamid türevleri ve bunların sitotoksik etkisinin değerlendirilmesi

Yıl 2024, Cilt: 17 Sayı: 2, 104 – 116, 30.06.2024

Asaf Evrim Evren , Sam Dawbaa , Demokrat Nuha , Aybüke Züleyha Kaya , Zerrin Canturk , Leyla Yurttaş

https://doi.org/10.30607/kvj.1430771

Öz

Bu çalışmada A549 küçük olmayan akciğer epitelyal karsinomu, Caco-2 kolon karsinomu ve SHSY-5Y nöroblastoma hücrelerine karşı kullanılabilecek yüksek seçiciliğe sahip antikanser bileşik(ler)in belirlenmesi temel amaçtır. Bu amaçla çalışma grubumuz tiyazol içeren dört bileşik (3a-3d) ve etil (4-metil-tiyazol-5-il)karboksilat içeren dört bileşik (3e-3h) şeklinde benzer iki asetamit serisi sentezledi. Sekiz bileşiğin yapısal analizleri HRMS, 1H-NMR ve 13C-NMR ile tanımlandı. Saflık onaylandıktan sonra yukarıdaki kanser hücrelerine karşı antikanser profilleri değerlendirildi ve ayrıca NIH/3T3 fibroblast hücrelerine karşı sitotoksisite etkisi test edildi. Bu arada ADME ve DFT hesaplamaları bileşiklerin iyi ADME profillerine ve kimyasal stabiliteye sahip olduğu belirlendi. Hedeflenen bileşikler arasında bileşik 3g daha fazla stabilite sergilemektedir. Kimyasal sistemlerde stabilite önemlidir çünkü bir molekül içindeki enerji dengesini temsil eder. Sonuçlar, bileşiklerin SHSY-5Y hücreleri üzerinde diğer hücrelere göre daha seçici bir etkiye sahip olduğunu gösterdi. Tiyazol üzerindeki ester grubu ile tiyazolidin (bileşik 3g) kombinasyonunun doksorubisinden anlamlı derecede etkili olduğu ve SHSY-5Y hücreleri üzerinde sağlıklı hücrelere göre oldukça seçici olduğu bulundu. Bunun yanı sıra, tiyazol-triazol kombinasyonu (3d ve 3h) üç kanser hücresinde de antiproliferatif aktiviteyi azaltırken, sağlıklı hücrede sitotoksisiteyi arttırdı. Bu çalışma ile nöroblastoma ve bununla ilişkili hastalıkların tedavisine ilişkin çalışmalarda etil 2-asetamido-4-metiltiyazol-5-karboksilat ve tiyazolin kombinasyonunun gelecekteki yaklaşımlar için ümit verici olduğunu ileri sürmektedir.

Anahtar Kelimeler

Tiyazol, Etil karboksilat, DFT, Antikanser aktivite, SHSY-5Y

Kaynakça

• Ahmed, K., Matsuya, Y., Nemoto, H., Zaidi, S.F., Sugiyama, T., Yoshihisa, Y., Shimizu, T., Kondo, T. (2009). Mechanism of apoptosis induced by a newly synthesized derivative of macrosphelides with a thiazole side chain. Chem Biol Interact, 177 (3), 218-226. 10.1016/j.cbi.2008.10.030
• Altintop, M.D., Kaplancikli, Z.A., Ciftci, G.A., Demirel, R. (2014). Synthesis and biological evaluation of thiazoline derivatives as new antimicrobial and anticancer agents. Eur. J. Med. Chem., 74, 264-277. 10.1016/j.ejmech.2013.12.060
• Bhagat, D.S., Chawla, P.A., Gurnule, W.B., Shejul, S.K., Bumbrah, G.S. (2021). An Insight into Synthesis and Anticancer Potential of Thiazole and 4-thiazolidinone Containing Motifs. Current Organic Chemistry, 25 (7), 819-841. 10.2174/1385272825999210101234704
• Bhat, U.G., Halasi, M., Gartel, A.L. (2009). Thiazole antibiotics target FoxM1 and induce apoptosis in human cancer cells. PLoS One, 4 (5), e5592. 10.1371/journal.pone.0005592
• Catarzi, D., Varano, F., Vigiani, E., Lambertucci, C., Spinaci, A., Volpini, R., Colotta, V. (2022). Casein Kinase 1delta Inhibitors as Promising Therapeutic Agents for Neurodegenerative Disorders. Curr Med Chem, 29 (27), 4698-4737. 10.2174/0929867329666220301115124
• Cavalier, H., Trasande, L., Porta, M. (2023). Exposures to pesticides and risk of cancer: Evaluation of recent epidemiological evidence in humans and paths forward. International Journal of Cancer, 152 (5), 879-912.
• Cortes, A.J. (2019). Molecular biology of cancer: similarities between humans and animals. Revista Veterinaria y Zootecnia (On Line), 13 (2), 81-95.
• Dawbaa, S., Evren, A.E., Cantürk, Z., Yurttaş, L. (2021). Synthesis of new thiazole derivatives and evaluation of their antimicrobial and cytotoxic activities. Phosphorus Sulfur Silicon Relat Elem, 196 (12), 1093-1102. 10.1080/10426507.2021.1972299
• Dawbaa, S., Nuha, D., Evren, A.E., Cankiliç, M.Y., Yurttaş, L., Turan, G. (2023). New oxadiazole/triazole derivatives with antimicrobial and antioxidant properties. J Mol Struct, 1282, 135213. 10.1016/j.molstruc.2023.135213
• Delaney, G., Jacob, S., Featherstone, C., Barton, M. (2005). The role of radiotherapy in cancer treatment: estimating optimal utilization from a review of evidence-based clinical guidelines. Cancer, 104 (6), 1129-1137. 10.1002/cncr.21324
• Dennington, R., Keith, T., Millam, J. (2009): GaussView, version 5.
• Dileep, K., Katiki, M.R., Rao, B.R., Vardhan, V.P.S.V., Sistla, R., Nanubolu, B., Murty, M.S.R. (2017). Regioselective synthesis and preliminary cytotoxic activity properties of tetrazole appendage N-substituted piperazine derivatives. Organic Communications, 10 (3), 178-189. 10.25135/acg.oc.20.17.04.018
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