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Imidazole and Quinoline-Based Promising Agent for Cancer Treatment; Synthesis, Characterization, and Computational Calculations

Year 2024, , 798 - 810, 20.08.2024

Tolga Acar Yeşil , Ömer Dilek , Tahir Tilki

https://doi.org/10.35414/akufemubid.1432554

Abstract

In this study, a novel imidazole and quinoline-based azo compound (MITPDQ) was synthesized, starting from aniline derivative which was used as an intermediate to synthesize nilotinib, which was used in leukemia treatment, characterized, and its structure was elucidated with spectroscopic techniques such as NMR, FTIR, UV, FTIR, and MS. Theoretical calculations using DFT (B3LYP) method and 6-311G (d,p) basis set were done to obtain optimized geometry and spectral data of MITPDQ. Experimental results were compared with theoretical ones and it was observed that they were compatible with each other. Using the optimized geometry of MITPDQ, the molecular docking studies were also conducted with cancer-related proteins. From docking results, the highest docking score was found to be -11.0 kcal/mol between MITPDQ and 2XIR protein. Also, the ADMET properties of MITPDQ were calculated. From ADMET and docking studies, it was concluded that the MITPDQ has the potential to be a drug candidate after further investigations were done related with this field.

Keywords

Imidazole Quinoline Quantum Chemical Calculations Molecular Docking ADMET

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İmidazol ve Kinolin Bazlı Kanser Tedavisi için Ümit Verici Ajan; Sentezi, Karakterizasyonu ve Bilgisayarsal Hesaplamaları

Year 2024, , 798 - 810, 20.08.2024

Tolga Acar Yeşil , Ömer Dilek , Tahir Tilki

https://doi.org/10.35414/akufemubid.1432554

Abstract

Bu çalışmada lösemi tedavisinde kullanılan nilotinibin sentezinde ara madde olarak kullanılan anilin türevinden yola çıkılarak yeni bir imidazol ve kinolin bazlı azo bileşiği (MITPDQ) sentezlendi ve sentezlenen maddenin yapısı NMR, FTIR, UV, FTIR ve MS gibi tekniklerle karakterize edildi. MITPDQ'nun optimize edilmiş geometrisini ve spektral verilerini elde etmek için DFT (B3LYP) yöntemi ve 6-311G (d,p) temel seti kullanılarak teorik hesaplamalar yapıldı. Deneysel sonuçlar teorik sonuçlarla karşılaştırıldı ve birbirleriyle uyumlu oldukları görüldü. MITPDQ'nun optimize edilmiş geometrisi kullanılarak, kanserle ilişkili proteinlerle de moleküler yerleştirme çalışmaları gerçekleştirildi. Yerleştirme sonuçlarından en yüksek yerleştirme puanının MITPDQ ile 2XIR proteini arasında -11,0 kcal/mol olduğu bulundu. Ayrıca MITPDQ'nun ADMET özellikleri de hesaplandı. ADMET ve Moleküler yerleştirme çalışmalarından bu alanla ilgili ileri araştırmalar yapılarak MITPDQ'nun ilaç adayı olma potansiyeline sahip olduğu sonucuna varıldı.

Keywords

İmidazol Kinolin Kuantum Kimyasal Hesaplamalar Moleküler Yerleştirme ADMET

References

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  • Jiménez, J., Doerr, S., Martínez-Rosell, G., Rose, A. S., & De Fabritiis, G., 2017. DeepSite: protein-binding site predictor using 3D-convolutional neural networks. Bioinformatics, 33(19), 3036–3042. https://doi.org/10.1093/bioinformatics/btx350
  • Jung, H., Kim, J., Im, D., Moon, H., & Hah, J.-M., 2019. Design, synthesis, and in vitro evaluation of N-(3-(3-alkyl-1H-pyrazol-5-yl) phenyl)-aryl amide for selective RAF inhibition. Bioorganic & Medicinal Chemistry Letters, 29(4), 534–538. https://doi.org/10.1016/j.bmcl.2019.01.003
  • Kalinichenko, E., Faryna, A., Bozhok, T., Golyakovich, A., & Panibrat, A., 2023. Novel Phthalic-Based Anticancer Tyrosine Kinase Inhibitors: Design, Synthesis and Biological Activity. Current Issues in Molecular Biology, 45(3), 1820–1842. https://doi.org/10.3390/cimb45030117
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There are 49 citations in total.

Details

Primary Language English
Subjects Atomic, Molecular and Optical Physics (Other), Physical Chemistry (Other)
Journal Section Articles
Authors

Tolga Acar Yeşil 0000-0001-5983-8447

Ömer Dilek 0000-0003-1409-782X

Tahir Tilki 0000-0002-1040-2375

Early Pub Date July 23, 2024
Publication Date August 20, 2024
Submission Date February 6, 2024
Acceptance Date June 20, 2024
Published in Issue Year 2024

Cite

APA Yeşil, T. A., Dilek, Ö., & Tilki, T. (2024). Imidazole and Quinoline-Based Promising Agent for Cancer Treatment; Synthesis, Characterization, and Computational Calculations. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, 24(4), 798-810. https://doi.org/10.35414/akufemubid.1432554
AMA Yeşil TA, Dilek Ö, Tilki T. Imidazole and Quinoline-Based Promising Agent for Cancer Treatment; Synthesis, Characterization, and Computational Calculations. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. August 2024;24(4):798-810. doi:10.35414/akufemubid.1432554
Chicago Yeşil, Tolga Acar, Ömer Dilek, and Tahir Tilki. “Imidazole and Quinoline-Based Promising Agent for Cancer Treatment; Synthesis, Characterization, and Computational Calculations”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 24, no. 4 (August 2024): 798-810. https://doi.org/10.35414/akufemubid.1432554.
EndNote Yeşil TA, Dilek Ö, Tilki T (August 1, 2024) Imidazole and Quinoline-Based Promising Agent for Cancer Treatment; Synthesis, Characterization, and Computational Calculations. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 24 4 798–810.
IEEE T. A. Yeşil, Ö. Dilek, and T. Tilki, “Imidazole and Quinoline-Based Promising Agent for Cancer Treatment; Synthesis, Characterization, and Computational Calculations”, Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, vol. 24, no. 4, pp. 798–810, 2024, doi: 10.35414/akufemubid.1432554.
ISNAD Yeşil, Tolga Acar et al. “Imidazole and Quinoline-Based Promising Agent for Cancer Treatment; Synthesis, Characterization, and Computational Calculations”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 24/4 (August 2024), 798-810. https://doi.org/10.35414/akufemubid.1432554.
JAMA Yeşil TA, Dilek Ö, Tilki T. Imidazole and Quinoline-Based Promising Agent for Cancer Treatment; Synthesis, Characterization, and Computational Calculations. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2024;24:798–810.
MLA Yeşil, Tolga Acar et al. “Imidazole and Quinoline-Based Promising Agent for Cancer Treatment; Synthesis, Characterization, and Computational Calculations”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, vol. 24, no. 4, 2024, pp. 798-10, doi:10.35414/akufemubid.1432554.
Vancouver Yeşil TA, Dilek Ö, Tilki T. Imidazole and Quinoline-Based Promising Agent for Cancer Treatment; Synthesis, Characterization, and Computational Calculations. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2024;24(4):798-810.


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