In silico approach to target PI3K/Akt/mTOR axis by selected Olea europaea phenols in PIK3CA mutant colorectal cancer

References

• Afrin, S., Giampieri, F., Gasparrini, M., Forbes-Hernández, T. Y., Cianciosi, D., Reboredo-Rodriguez, P., Zhang, J., Manna, P. P., Daglia, M., Atanasov, A. G., & Battino, M. (2020). Dietary phytochemicals in colorectal cancer prevention and treatment: A focus on the molecular mechanisms involved. Biotechnology Advances, 38, 107322. https://doi.org/10.1016/j.biotechadv.2018.11.011
   PubMed Web of Science ®Google Scholar
• Bahrami, A., Khazaei, M., Hasanzadeh, M., Shahid Sales, S., Joudi Mashhad, M., Farazestanian, M., Sadeghnia, H. R., Rezayi, M., Maftouh, M., Hassanian, S. M., & Avan, A. (2018). Therapeutic potential of targeting PI3K/AKT pathway in treatment of colorectal cancer: Rational and progress. Journal of Cell Biochemistry, 119(3), 2460–2469. https://doi.org/10.1002/jcb.25950
   PubMed Web of Science ®Google Scholar
• Banavath, H. N., Sharma, O. P., Kumar, M. S., & Baskaran, R. (2014). Identification of novel tyrosine kinase inhibitors for drug resistant T315I mutant BCR-ABL: A virtual screening and molecular dynamics simulations study. Scientific Reports, 4, 6948. https://doi.org/10.1038/srep06948
   PubMed Web of Science ®Google Scholar
• Bonvino, N. P., Liang, J., McCord, E. D., Zafiris, E., Benetti, N., Ray, N. B., Hung, A., Boskou, D., & Karagiannis, T. C. (2018). OliveNetTM: A comprehensive library of compounds from Olea europaea. Database, 2018, bay016. https://doi.org/10.1093/database/bay016
   PubMedGoogle Scholar
• Borzì, A., Biondi, A., Basile, F., Luca, S., Vicari, E., & Vacante, M. (2018). Olive oil effects on colorectal cancer. Nutrients, 11(1), 32. https://doi.org/10.3390/nu11010032
   PubMed Web of Science ®Google Scholar
• Castejón, M. L., Montoya, T., Alarcón-de-la-Lastra, C., & Sánchez-Hidalgo, M. (2020). Potential protective role exerted by secoiridoids from Olea europaea L. in cancer, cardiovascular, neurodegenerative, aging-related, and immunoinflammatory diseases. Antioxidants, 9(2), 149. https://doi.org/10.3390/antiox9020149
   Web of Science ®Google Scholar
• Chen, Y., Lee, C. H., & Tseng, B. Y. (2018). AZD8055 exerts antitumor effects on colon cancer cells by inhibiting mTOR and cell-cycle progression. Anticancer Research, 38, 1445–1454. https://doi.org/10.21873/anticanres.12369
   PubMed Web of Science ®Google Scholar
• Chunhua, L., Donglan, L., Xiuqiong, F., Lihua, Z., Qin, F., Yawei, L., Liang, Z., Ge, W., Linlin, J., Ping, Z., Kun, L., & Xuegang, S. (2013). Apigenin up-regulates transgelin and inhibits invasion and migration of colorectal cancer through decreased phosphorylation of AKT. The Journal of Nutritional Biochemistry, 24(10), 1766–1775. https://doi.org/10.1016/j.jnutbio.2013.03.006
   PubMed Web of Science ®Google Scholar
• Dannenberg, J. J. (1998). An Introduction to Hydrogen Bonding By George A. Jeffrey (University of Pittsburgh). Oxford University Press. (1997). ix + 303. pp. $60.00. ISBN 0-19-509549-9. Journal of the American Chemical Society 120:5604–5604. https://doi.org/10.1021/ja9756331
   Google Scholar
• Drott, J., Starkhammar, H., Kjellgren, K., & Berterö, C. (2018). Neurotoxic side effects early in the oxaliplatin treatment period in patients with colorectal cancer. ONF, 45, 690–697. https://doi.org/10.1188/18.ONF.690-697
   PubMed Web of Science ®Google Scholar
• Erbaş, A., de la Cruz, M. O., & Marko, J. F. (2018). Effects of electrostatic interactions on ligand dissociation kinetics. Physical Review E, 97, 022405. https://doi.org/10.1103/PhysRevE.97.022405.
   Google Scholar
• Foley, T. M., Payne, S. N., Pasch, C. A., Yueh, A. E., Van De Hey, D. R., Korkos, D. P., Clipson, L., Maher, M. E., Matkowskyj, K. A., Newton, M. A., & Deming, D. A. (2017). Dual PI3K/mTOR inhibition in colorectal cancers with APC and PIK3CA mutations. Molecular Cancer Research, 15(3), 317–327. https://doi.org/10.1158/1541-7786.MCR-16-0256
   PubMed Web of Science ®Google Scholar
• Giner, E., Recio, M. C., Ríos, J. L., Cerdá-Nicolás, J. M., & Giner, R. M. (2016). Chemopreventive effect of oleuropein in colitis-associated colorectal cancer in c57bl/6 mice. Molecular Nutrition & Food Research, 60(2), 242–255. https://doi.org/10.1002/mnfr.201500605
   PubMed Web of Science ®Google Scholar
• Hamada, T., Nowak, J. A., & Ogino, S. (2017). PIK3CA mutation and colorectal cancer precision medicine. Oncotarget, 8(14), 22305–22306. https://doi.org/10.18632/oncotarget.15724
   PubMedGoogle Scholar
• Hashmi, M. A., Khan, A., Hanif, M., Farooq, U., & Perveen, S. (2015). Traditional uses, phytochemistry, and pharmacology of Olea europaea (Olive). Evidence-Based Complementary and Alternative Medicine : eCAM, 2015, 541591–541529. https://doi.org/10.1155/2015/541591
   PubMed Web of Science ®Google Scholar
• Heerding, D. A., Rhodes, N., Leber, J. D., Clark, T. J., Keenan, R. M., Lafrance, L. V., Li, M., Safonov, I. G., Takata, D. T., Venslavsky, J. W., Yamashita, D. S., Choudhry, A. E., Copeland, R. A., Lai, Z., Schaber, M. D., Tummino, P. J., Strum, S. L., Wood, E. R., Duckett, D. R., … Kumar, R. (2008). Identification of 4-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-{[(3 S) -3-piperidinylmethyl]oxy}-1 H -imidazo[4,5- c] pyridin-4-yl)-2-methyl-3-butyn-2-ol (GSK690693), a novel inhibitor of AKT kinase. Journal of Medicinal Chemistry, 51(18), 5663–5679. https://doi.org/10.1021/jm800452
   PubMed Web of Science ®Google Scholar
• Je, I.-G., Kim, D.-S., Kim, S.-W., Lee, S., Lee, H.-S., Park, E. K., Khang, D., & Kim, S.-H. (2015). Tyrosol suppresses allergic inflammation by inhibiting the activation of phosphoinositide 3-kinase in mast cells. PLoS ONE, 10(6), e0129829. https://doi.org/10.1371/journal.pone.0129829
   PubMed Web of Science ®Google Scholar
• Kim, S., Chen, J., Cheng, T., Gindulyte, A., He, J., He, S., Li, Q., Shoemaker, B. A., Thiessen, P. A., Yu, B., Zaslavsky, L., Zhang, J., & Bolton, E. E. (2019). PubChem 2019 update: Improved access to chemical data. Nucleic Acids Research, 47(D1), D1102–D1109. https://doi.org/10.1093/nar/gky1033
   PubMed Web of Science ®Google Scholar
• Koveitypour, Z., Panahi, F., Vakilian, M., Peymani, M., Seyed Forootan, F., Nasr Esfahani, M. H., & Ghaedi, K. (2019). Signaling pathways involved in colorectal cancer progression. Cell & Bioscience, 9, 97. https://doi.org/10.1186/s13578-019-0361-4
   PubMed Web of Science ®Google Scholar
• Kumari, R., Kumar, R., & Lynn, A., Open Source Drug Discovery Consortium. (2014). g_mmpbsa-a GROMACS tool for high-throughput MM-PBSA calculations. Journal of Chemical Information and Modeling, 54(7), 1951–1962. https://doi.org/10.1021/ci500020m
   PubMed Web of Science ®Google Scholar
• Lemkul, J. (2019). From proteins to perturbed Hamiltonians: A suite of tutorials for the GROMACS-2018 Molecular Simulation Package. Living Journal of Computational Molecular Science, 1(1), 5068. https://doi.org/10.33011/livecoms.1.1.5068
   Google Scholar
• Liu, M., Wang, J., Huang, B., Chen, A., & Li, X. (2016). Oleuropein inhibits the proliferation and invasion of glioma cells via suppression of the AKT signaling pathway. Oncology Reports, 36(4), 2009–2016. https://doi.org/10.3892/or.2016.4978
   PubMed Web of Science ®Google Scholar
• Lynch, T., & Price, A. (2007). The effect of cytochrome P450 metabolism on drug response, interactions, and adverse effects. American Family Physician, 76(3), 391–396.
   PubMed Web of Science ®Google Scholar
• Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. J. (2009). AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30(16), 2785–2791. https://doi.org/10.1002/jcc.21256
   PubMed Web of Science ®Google Scholar
• Nagappan, A., Lee, W. S., Yun, J. W., Lu, J. N., Chang, S.-H., Jeong, J.-H., Kim, G. S., Jung, J.-M., & Hong, S. C. (2017). Tetraarsenic hexoxide induces G2/M arrest, apoptosis, and autophagy via PI3K/Akt suppression and p38 MAPK activation in SW620 human colon cancer cells. PLoS ONE, 12(3), e0174591 https://doi.org/10.1371/journal.pone.0174591
   PubMed Web of Science ®Google Scholar
• Narayanankutty, A. (2019). PI3K/ Akt/ mTOR pathway as a therapeutic target for colorectal cancer: A review of preclinical and clinical evidence. Current Drug Targets, 20(12), 1217–1226. https://doi.org/10.2174/1389450120666190618123846
   PubMed Web of Science ®Google Scholar
• Nitulescu, G., Van De Venter, M., Nitulescu, G., Ungurianu, A., Juzenas, P., Peng, Q., Olaru, O., Grădinaru, D., Tsatsakis, A., Tsoukalas, D., Spandidos, D., & Margina, D. (2018). The Akt pathway in oncology therapy and beyond (Review). International Journal of Oncology, 53(6), 2319–2331. https://doi.org/10.3892/ijo.2018.4597
   Google Scholar
• Park, Y.-L., Kim, H.-P., Cho, Y.-W., Min, D.-W., Cheon, S.-K., Lim, Y. J., Song, S.-H., Kim, S. J., Han, S.-W., Park, K. J., & Kim, T.-Y. (2019). Activation of WNT/β-catenin signaling results in resistance to a dual PI3K/mTOR inhibitor in colorectal cancer cells harboring PIK3CA mutations: Resistance mechanism of a dual PI3K/mTOR inhibitor. International Journal of Cancer, 144(2), 389–401. https://doi.org/10.1002/ijc.31662
   PubMed Web of Science ®Google Scholar
• Pei, Y-h., Chen, J., Xie, L., Cai, X-m., Yang, R.-H., Wang, X., & Gong, J-b. (2016). Hydroxytyrosol protects against myocardial ischemia/reperfusion injury through a PI3K/Akt-dependent mechanism. Mediators of Inflammation, 2016, 1232103–1232109. https://doi.org/10.1155/2016/1232103
   PubMed Web of Science ®Google Scholar
• Pires, D. E. V., Blundell, T. L., & Ascher, D. B. (2015). pkCSM: Predicting small-molecule pharmacokinetic and toxicity properties using graph-based signatures. Journal of Medicinal Chemistry, 58(9), 4066–4072. https://doi.org/10.1021/acs.jmedchem.5b00104
   PubMed Web of Science ®Google Scholar
• Polini, B., Digiacomo, M., Carpi, S., Bertini, S., Gado, F., Saccomanni, G., Macchia, M., Nieri, P., Manera, C., & Fogli, S. (2018). Oleocanthal and oleacein contribute to the in vitro therapeutic potential of extra virgin oil-derived extracts in non-melanoma skin cancer. Toxicology in Vitro : An International Journal Published in Association with BIBRA, 52, 243–250. https://doi.org/10.1016/j.tiv.2018.06.021
   PubMed Web of Science ®Google Scholar
• Rigacci, S., Miceli, C., Nediani, C., Berti, A., Cascella, R., Pantano, D., Nardiello, P., Luccarini, I., Casamenti, F., & Stefani, M. (2015). Oleuropein aglycone induces autophagy via the AMPK/mTOR signalling pathway: A mechanistic insight. Oncotarget, 6(34), 35344–35357. https://doi.org/10.18632/oncotarget.6119
   PubMedGoogle Scholar
• Sabri, M. Z., Abdul Hamid, A. A., Sayed Hitam, S. M., & Abdul Rahim Mohd, Z. (2019). In silico screening of aptamers configuration against hepatitis B surface antigen. Advances in Bioinformatics, 2019, 6912914–6912912. https://doi.org/10.1155/2019/6912914
   PubMedGoogle Scholar
• Sánchez-Fidalgo, S., Villegas, I., Aparicio-Soto, M., Cárdeno, A., Rosillo, M. Á., González-Benjumea, A., Marset, A., López, Ó., Maya, I., Fernández-Bolaños, J. G., & Alarcón de la Lastra, C. (2015). Effects of dietary virgin olive oil polyphenols: Hydroxytyrosyl acetate and 3, 4-dihydroxyphenylglycol on DSS-induced acute colitis in mice. The Journal of Nutritional Biochemistry, 26(5), 513–520. https://doi.org/10.1016/j.jnutbio.2014.12.001
   PubMed Web of Science ®Google Scholar
• Sanguinetti, M. C. (2014). HERG1 channel agonists and cardiac arrhythmia. Current Opinion in Pharmacology, 15, 22–27. https://doi.org/10.1016/j.coph.2013.11.006
   PubMed Web of Science ®Google Scholar
• Scotece, M., Gómez, R., Conde, J., Lopez, V., Gómez-Reino, J. J., Lago, F., Smith, A. B., & Gualillo, O. (2013). Oleocanthal inhibits proliferation and MIP-1α expression in human multiple myeloma cells. Current Medicinal Chemistry, 20(19), 2467–2475. https://doi.org/10.2174/0929867311320190006
   PubMed Web of Science ®Google Scholar
• Siegel, R. L., Miller, K. D., Goding Sauer, A., Fedewa, S. A., Butterly, L. F., Anderson, J. C., Cercek, A., Smith, R. A., & Jemal, A. (2020). Colorectal cancer statistics, 2020. CA: A Cancer Journal for Clinicians, 70(3), 145–164. https://doi.org/10.3322/caac.21601
   PubMed Web of Science ®Google Scholar
• Stoneham, M., Goldacre, M., Seagroatt, V., & Gill, L. (2000). Olive oil, diet and colorectal cancer: An ecological study and a hypothesis. Journal of Epidemiology and Community Health, 54 (10), 756–760. https://doi.org/10.1136/jech.54.10.756
   PubMed Web of Science ®Google Scholar
• Stuttfeld, E., Aylett, C. H., Imseng, S., Boehringer, D., Scaiola, A., Sauer, E., Hall, M. N., Maier, T., & Ban, N. (2018). Architecture of the human mTORC2 core complex. eLife, 7, e33101. https://doi.org/10.7554/eLife.33101
   PubMed Web of Science ®Google Scholar
• Veber, D. F., Johnson, S. R., Cheng, H.-Y., Smith, B. R., Ward, K. W., & Kopple, K. D. (2002). Molecular properties that influence the oral bioavailability of drug candidates. Journal of Medicinal Chemistry, 45(12), 2615–2623. https://doi.org/10.1021/jm020017n
   PubMed Web of Science ®Google Scholar
• Wang, C., Greene, D., & Xiao, L. (2018). Recent developments and applications of the MMPBSA method. Frontiers in Molecular Biosciences., 4, 87. https://doi.org/10.3389/fmolb.2017.00087
   PubMed Web of Science ®Google Scholar
• Xavier, C. P. R., Lima, C. F., Preto, A., Seruca, R., Fernandes-Ferreira, M., & Pereira-Wilson, C. (2009). Luteolin, quercetin and ursolic acid are potent inhibitors of proliferation and inducers of apoptosis in both KRAS and BRAF mutated human colorectal cancer cells. Cancer Letters, 281(2), 162–170. https://doi.org/10.1016/j.canlet.2009.02.041
   PubMed Web of Science ®Google Scholar
• Xing, C., Zhu, B., Liu, H., Yao, H., & Zhang, L. (2008). Class I phosphatidylinositol 3-kinase inhibitor LY294002 activates autophagy and induces apoptosis through p53 pathway in gastric cancer cell line SGC7901. Acta Biochimica et Biophysica Sinica, 40(3), 194–201. https://doi.org/10.1111/j.1745-7270.2008.00393.x
   PubMed Web of Science ®Google Scholar
• Xu, F., Na, L., Li, Y., & Chen, L. (2020). Roles of the PI3K/AKT/mTOR signalling pathways in neurodegenerative diseases and tumours. Cell & Bioscience, 10, 54. https://doi.org/10.1186/s13578-020-00416-0
   PubMed Web of Science ®Google Scholar
• Yang, J., Pi, C., & Wang, G. (2018). Inhibition of PI3K/Akt/mTOR pathway by apigenin induces apoptosis and autophagy in hepatocellular carcinoma cells. Biomedicine & Pharmacotherapy, 103, 699–707. https://doi.org/10.1016/j.biopha.2018.04.072
   PubMed Web of Science ®Google Scholar
• Yang, T., Li, X., Montazeri, Z., Little, J., Farrington, S. M., Ioannidis, J. P. A., Dunlop, M. G., Campbell, H., Timofeeva, M., & Theodoratou, E. (2019). Gene-environment interactions and colorectal cancer risk: An umbrella review of systematic reviews and meta-analyses of observational studies. International Journal of Cancer, 145(9), 2315–2329. https://doi.org/10.1002/ijc.32057
   PubMed Web of Science ®Google Scholar
• Yao, X., Jiang, W., Yu, D., & Yan, Z. (2019). Luteolin inhibits proliferation and induces apoptosis of human melanoma cells in vivo and in vitro by suppressing MMP-2 and MMP-9 through the PI3K/AKT pathway. Food & Function, 10(2), 703–712. https://doi.org/10.1039/c8fo02013b
   PubMed Web of Science ®Google Scholar
• Yu, J., Kwon, H., Cho, E., Jeon, J., Kang, R. H., Youn, K., Jun, M., Lee, Y. C., Ryu, J. H., & Kim, D. H. (2019). The effects of pinoresinol on cholinergic dysfunction-induced memory impairments and synaptic plasticity in mice. Food and Chemical Toxicology: An International Journal Published for the British Industrial Biological Research Association, 125, 376–382. https://doi.org/10.1016/j.fct.2019.01.017
   PubMed Web of Science ®Google Scholar