A study of the anticancer effect of 1,8 cineole: Molecular docking analysis

Yıl 2024, Cilt: 8 Sayı: 1, 50 - 55, 31.03.2024

Bilge Bıçak

https://doi.org/10.30516/bilgesci.1415844

Öz

Since cancer is a serious disease that affects many people around the world, scientists focus on studies on the diagnosis and treatment of cancer. Plants have been used for therapeutic purposes for many years. Plants that form the basis of traditional medicine contain therapeutic compounds. These compounds have important properties such as anticancer, anti-inflammatory, analgesic, antimicrobial and antioxidant. Essential oils obtained from various plants are known to have therapeutic effects. Terpenes make up the largest part of the composition of plant essential oils. Terpenes have various beneficial effects such as anti-anxiety, anti-depressant, anti-inflammatory, anti-bacterial, anti-cancer, analgesic and mood-boosting. 1,8 cineole is one of the monoterpene compounds found in essential oils. 1,8 cineole is an important compound with various properties such as antioxidant, anti-inflammatory and anticancer. The molecular docking method is one of the computational modeling methods used in drug development programs. In this study, the interactions of 1,8 cineole, which is known to have anticancer properties, with various receptors prominent in anticancer studies (estrogen receptor beta (ER-β), epidermal growth factor receptor (EGFR), Receptor tyrosine-protein kinase erbB-2 (HER2) and Tankyrase 1) were examined with the help of the molecular docking method, the interaction profile was determined and presented in comparison with literature studies. As a result of docking studies, it was predicted that the interaction with Tankyrase-1 would be stronger.

Anahtar Kelimeler

Essential oil, Molecular docking, Cancer, Plant

Destekleyen Kurum

The authors declared that this study has received no financial support.

Teşekkür

I would like to thank Prof. Dr. Uğur Gündüz and Prof. Dr. Serda Kecel Gündüz for their support.

Kaynakça

• Abdalla, A. N., Shaheen, U., Abdallah, Q. M., Flamini, G., Bkhaitan, M. M., Abdelhady, M. I., . . . Bader, A. (2020). Proapoptotic activity of Achillea membranacea essential oil and its major constituent 1, 8-cineole against A2780 ovarian cancer cells. Molecules, 25(7), 1582.
• Ahcene Djaballah, S., Daniel, F., Milani, A., Ricagno, G., & Lonardi, S. (2022). HER2 in colorectal cancer: the long and winding road from negative predictive factor to positive actionable target. American Society of Clinical Oncology Educational Book, 42, 219-232.
• Arqués, O., Chicote, I., Puig, I., Tenbaum, S. P., Argilés, G., Dienstmann, R., . . . Silberschmidt, D. (2016). Tankyrase inhibition blocks Wnt/β-catenin pathway and reverts resistance to PI3K and AKT inhibitors in the treatment of colorectal cancer. Clinical cancer research, 22(3), 644-656.
• Bethune, G., Bethune, D., Ridgway, N., & Xu, Z. (2010). Epidermal growth factor receptor (EGFR) in lung cancer: an overview and update. Journal of thoracic disease, 2(1), 48.
• de Castro-Carpeño, J., Belda-Iniesta, C., Sáenz, E. C., Agudo, E. H., Batlle, J. F., & Barón, M. G. (2008). EGFR and colon cancer: a clinical view. Clinical and Translational Oncology, 10, 6-13.
• Dehelean, C. A., Marcovici, I., Soica, C., Mioc, M., Coricovac, D., Iurciuc, S., . . . Pinzaru, I. (2021). Plant-derived anticancer compounds as new perspectives in drug discovery and alternative therapy. Molecules, 26(4), 1109.
• DeLano, W. L. (2002). Pymol: An open-source molecular graphics tool. CCP4 Newsl. Protein Crystallogr, 40(1), 82-92.
• Frisch, M., Trucks, G., Schlegel, H., Scuseria, G., Robb, M., Cheeseman, J., . . . Petersson, G. (2009). Gaussian 09 Revision A. 02, 2009, Gaussian Inc. Wallingford CT, 66, 219.
• Glaysher, S., Bolton, L., Johnson, P., Atkey, N., Dyson, M., Torrance, C., & Cree, I. (2013). Targeting EGFR and PI3K pathways in ovarian cancer. British journal of cancer, 109(7), 1786-1794.
• Hoch, C. C., Petry, J., Griesbaum, L., Weiser, T., Werner, K., Ploch, M., . . . Wollenberg, B. (2023). 1, 8-cineole (eucalyptol): A versatile phytochemical with therapeutic applications across multiple diseases. Biomedicine & Pharmacotherapy, 167, 115467.
• Hsu, L.-H., Chu, N.-M., & Kao, S.-H. (2017). Estrogen, estrogen receptor and lung cancer. International journal of molecular sciences, 18(8), 1713.
• Iqbal, N., & Iqbal, N. (2014). Human epidermal growth factor receptor 2 (HER2) in cancers: overexpression and therapeutic implications. Molecular biology international, 2014.
• Ishikawa, T., Seto, M., Banno, H., Kawakita, Y., Oorui, M., Taniguchi, T., . . . Miki, H. (2011). Design and synthesis of novel human epidermal growth factor receptor 2 (HER2)/epidermal growth factor receptor (EGFR) dual inhibitors bearing a pyrrolo [3, 2-d] pyrimidine scaffold. Journal of medicinal chemistry, 54(23), 8030-8050.
• Ivanova, M., Venetis, K., Guerini-Rocco, E., Bottiglieri, L., Mastropasqua, M. G., Garrone, O., . . . Ghidini, M. (2022). HER2 in metastatic colorectal cancer: pathology, somatic alterations, and perspectives for novel therapeutic schemes. Life, 12(9), 1403.
• Johannes, J. W., Almeida, L., Barlaam, B., Boriack-Sjodin, P. A., Casella, R., Croft, R. A., . . . Hawkins, J. L. (2015). Pyrimidinone nicotinamide mimetics as selective tankyrase and wnt pathway inhibitors suitable for in vivo pharmacology. ACS medicinal chemistry letters, 6(3), 254-259.
• Kamal, A., Riyaz, S., Kumar Srivastava, A., & Rahim, A. (2014). Tankyrase inhibitors as therapeutic targets for cancer. Current Topics in Medicinal Chemistry, 14(17), 1967-1976.
• Korkmaz, T. B., & Ayaz, F. (2023). Molecular docking: A powerful tool for predicting protein-ligand interactions. Advanced Engineering Days (AED), 7, 4-6.
• Lazennec, G. (2006). Estrogen receptor beta, a possible tumor suppressor involved in ovarian carcinogenesis. Cancer letters, 231(2), 151-157.
• Lee, S. (2006). Is EGFR expression important in non-small cell lung cancer? In (Vol. 61, pp. 98-99): BMJ Publishing Group Ltd.
• Manas, E. S., Xu, Z. B., Unwalla, R. J., & Somers, W. S. (2004). Understanding the selectivity of genistein for human estrogen receptor-β using X-ray crystallography and computational methods. Structure, 12(12), 2197-2207.
• Mehta, C. C., & Bhatt, H. G. (2021). Tankyrase inhibitors as antitumor agents: a patent update (2013–2020). Expert Opinion on Therapeutic Patents, 31(7), 645-661.
• Murata, S., Shiragami, R., Kosugi, C., Tezuka, T., Yamazaki, M., Hirano, A., . . . Ohkohchi, N. (2013). Antitumor effect of 1, 8-cineole against colon cancer. Oncology reports, 30(6), 2647-2652.
• Neagu, G., Stefaniu, A., Albulescu, A., Pintilie, L., & Pirvu, L. C. (2021). Antiproliferative Activity of Stokesia laevis Ethanolic Extract in Combination with Several Food-Related Bioactive Compounds; In Vitro (Caco-2) and In Silico Docking (TNKS1 and TNKS2) Studies. Applied Sciences, 11(21), 9944.
• Normanno, N., De Luca, A., Bianco, C., Strizzi, L., Mancino, M., Maiello, M. R., . . . Salomon, D. S. (2006). Epidermal growth factor receptor (EGFR) signaling in cancer. Gene, 366(1), 2-16.
• Prabhavathi, H., Dasegowda, K., Renukananda, K., Karunakar, P., Lingaraju, K., & Raja Naika, H. (2022). Molecular docking and dynamic simulation to identify potential phytocompound inhibitors for EGFR and HER2 as anti-breast cancer agents. Journal of Biomolecular Structure and Dynamics, 40(10), 4713-4724.
• Rego, R., Foster, N., Smyrk, T., Le, M., O'connell, M., Sargent, D., . . . Sinicrope, F. (2010). Prognostic effect of activated EGFR expression in human colon carcinomas: comparison with EGFR status. British journal of cancer, 102(1), 165-172.
• Riudavets, M., Sullivan, I., Abdayem, P., & Planchard, D. (2021). Targeting HER2 in non-small-cell lung cancer (NSCLC): a glimpse of hope? An updated review on therapeutic strategies in NSCLC harbouring HER2 alterations. ESMO open, 6(5), 100260.
• Rodenak-Kladniew, B., Castro, A., Stärkel, P., Galle, M., & Crespo, R. (2020). 1, 8-Cineole promotes G0/G1 cell cycle arrest and oxidative stress-induced senescence in HepG2 cells and sensitizes cells to anti-senescence drugs. Life sciences, 243, 117271.
• Rodenak-Kladniew, B., Castro, M. A., Crespo, R., Galle, M., & de Bravo, M. G. (2020). Anti-cancer mechanisms of linalool and 1, 8-cineole in non-small cell lung cancer A549 cells. Heliyon, 6(12).
• Sampath, S., Subramani, S., Janardhanam, S., Subramani, P., Yuvaraj, A., & Chellan, R. (2018). Bioactive compound 1, 8-Cineole selectively induces G2/M arrest in A431 cells through the upregulation of the p53 signaling pathway and molecular docking studies. Phytomedicine, 46, 57-68.
• Sasaki, T., Hiroki, K., & Yamashita, Y. (2013). The role of epidermal growth factor receptor in cancer metastasis and microenvironment. BioMed research international, 2013.
• Schüler-Toprak, S., Moehle, C., Skrzypczak, M., Ortmann, O., & Treeck, O. (2017). Effect of estrogen receptor β agonists on proliferation and gene expression of ovarian cancer cells. BMC cancer, 17, 1-9.
• Shi, J. H., Guo, W. Z., Jin, Y., Zhang, H.-P., Pang, C., Li, J., . . . Zhang, S. J. (2019). Recognition of HER2 expression in hepatocellular carcinoma and its significance in postoperative tumor recurrence. Cancer medicine, 8(3), 1269-1278.
• Siegfried, J. M. (2001). Women and lung cancer: does oestrogen play a role? The lancet oncology, 2(8), 506-513. Slamon, D. J., Godolphin, W., Jones, L. A., Holt, J. A., Wong, S. G., Keith, D. E., . . . Ullrich, A. (1989). Studies of the HER-2/neu proto-oncogene in human breast and ovarian cancer. Science, 244(4905), 707-712.
• Solberg, N. T., Waaler, J., Lund, K., Mygland, L., Olsen, P. A., & Krauss, S. (2018). TANKYRASE inhibition enhances the antiproliferative effect of PI3K and EGFR inhibition, mutually affecting β-CATENIN and AKT signaling in colorectal cancer. Molecular Cancer Research, 16(3), 543-553.
• Stamos, J., Sliwkowski, M. X., & Eigenbrot, C. (2002). Structure of the epidermal growth factor receptor kinase domain alone and in complex with a 4-anilinoquinazoline inhibitor. Journal of biological chemistry, 277(48), 46265-46272.
• Studio, D. (2008). Discovery studio. Accelrys [2.1].
• Treeck, O., Pfeiler, G., Mitter, D., Lattrich, C., Piendl, G., & Ortmann, O. (2007). Estrogen receptor β1 exerts antitumoral effects on SK-OV-3 ovarian cancer cells. Journal of Endocrinology, 193(3), 421-433.
• Trott, O., & Olson, A. J. (2010). AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of computational chemistry, 31(2), 455-461.
• Verma, A., Kumar, A., Chugh, A., Kumar, S., & Kumar, P. (2021). Tankyrase inhibitors: emerging and promising therapeutics for cancer treatment. Medicinal Chemistry Research, 30, 50-73.
• Williams, C., DiLeo, A., Niv, Y., & Gustafsson, J.-Å. (2016). Estrogen receptor beta as target for colorectal cancer prevention. Cancer letters, 372(1), 48-56.