Insight of druggable cannabinoids against estrogen receptor β in breast cancer

References

• Anestis, A., Sarantis, P., Theocharis, S., Zoi, I., Tryfonopoulos, D., Korogiannos, A., Koumarianou, A., Xingi, E., Thomaidou, D., Kontos, M., Papavassiliou, A. G., & Karamouzis, M. V. (2019). Estrogen receptor beta increases sensitivity to enzalutamide in androgen receptor-positive triple-negative breast cancer. Journal of Cancer Research and Clinical Oncology, 145(5), 1221–1233. doi:10.1007/s00432-019-02872-9
   PubMed Web of Science ®Google Scholar
• Bajorath, J. (2002). Integration of virtual and high-throughput screening. Nature Reviews Drug Discovery, 1(11), 882–894. doi:10.1038/nrd941
   PubMed Web of Science ®Google Scholar
• Balani, S., Miwa, G., Gan, L.-S., Wu, J.-T., & Lee, F. (2005). Strategy of utilizing in vitro and in vivo ADME tools for lead optimization and drug candidate selection. Current Topics in Medicinal Chemistry, 5(11), 1033–1038. doi:10.2174/156802605774297038
   PubMed Web of Science ®Google Scholar
• Banerjee, P., Eckert, A. O., Schrey, A. K., & Preissner, R. (2018). ProTox-II: A webserver for the prediction of toxicity of chemicals. Nucleic Acids Research, 46(W1), W257–W263. doi:10.1093/nar/gky318
   PubMed Web of Science ®Google Scholar
• Berman, H. M., Westbrook, J., Feng, Z., Gilliland, G., Bhat, T. N., Weissig, H., Shindyalov, I. N., & Bourne, P. E. (2000). The Protein Data Bank Helen. Nucleic Acids Research, 28(1), 235–242. doi:10.1093/nar/28.1.235
   PubMed Web of Science ®Google Scholar
• Birdsall, S. M., Birdsall, T. C., & Tims, L. A. (2016). The use of medical marijuana in cancer. Current Oncology Reports, 18(7). doi:10.1007/s11912-016-0530-0
   PubMed Web of Science ®Google Scholar
• Chakravarti, B., Ravi, J., & Ganju, R. K. (2014). Cannabinoids as therapeutic agents in cancer: Current status and future implications. Oncotarget, 5(15), 5852–5872. doi:10.18632/oncotarget.2233
   Google Scholar
• Chien, A., Foster, I., & Goddette, D. (2002). Grid technologies empowering drug discovery. Drug Discovery Today, 7(20), s176–s180. doi:10.1016/S1359-6446(02)02369-3
   PubMed Web of Science ®Google Scholar
• Chuang, S. C., Wu, G. J., Lu, Y. S., Lin, C. H., & Hsiung, C. A. (2015). Associations between medical conditions and breast cancer risk in Asians: A nationwide population-based study in Taiwan. PLoS One.doi:10.1371/journal.pone.0143410
   Google Scholar
• Daina, A., Michielin, O., & Zoete, V. (2014). ILOGP: A simple, robust, and efficient description of n-octanol/water partition coefficient for drug design using the GB/SA approach. Journal of Chemical Information and Modeling, 54(12), 3284–3301. doi:10.1021/ci500467k
   PubMed Web of Science ®Google Scholar
• Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific Reports, 7(1). doi:10.1038/srep42717
   PubMed Web of Science ®Google Scholar
• Daina, A., & Zoete, V. (2016). A BOILED-egg to predict gastrointestinal absorption and brain penetration of small molecules. ChemMedChem, 11(11), 1117-21. doi:10.1002/cmdc.201600182
   PubMed Web of Science ®Google Scholar
• Ferlay, J., Colombet, M., Soerjomataram, I., Mathers, C., Parkin, D. M., Piñeros, M., Znaor, A., & Bray, F. (2019). Estimating the global cancer incidence and mortality in 2018: GLOBOCAN sources and methods. International Journal of Cancer, 144(8), 1941–1953. doi:10.1002/ijc.31937
   PubMed Web of Science ®Google Scholar
• Gruvberger-Saal, S. K., Bendahl, P. O., Saal, L. H., Laakso, M., Hegardt, C., Edén, P., Peterson, C., Malmström, P., Isola, J., Borg, Å., & Fernö, M. (2007). Estrogen receptor β expression is associated with tamoxifen response in ERα-negative breast carcinoma. Clinical Cancer Research, 13(7), 1987–1994. doi:10.1158/1078-0432.CCR-06-1823
   PubMed Web of Science ®Google Scholar
• Hieken, T. J., Carter, J. M., Hawse, J. R., Hoskin, T. L., Bois, M., Frost, M., Hartmann, L. C., Radisky, D. C., Visscher, D. W., & Degnim, A. C. (2015). ERβ expression and breast cancer risk prediction for women with atypias. Cancer Prevention Research, 8(11), 1084–1092. doi:10.1158/1940-6207.CAPR-15-0198
   PubMed Web of Science ®Google Scholar
• Hossain, M. U., Khan, M. A., Rakib-Uz-Zaman, S. M., Ali, M. T., Islam, M. S., Keya, C. A., & Salimullah, M. (2016). Treating diabetes mellitus: Pharmacophore based designing of potential drugs from Gymnema sylvestre against insulin receptor protein. BioMed Research International, 2016, 1–14. doi:10.1155/2016/3187647
   Web of Science ®Google Scholar
• Kisková, T., Mungenast, F., Suváková, M., Jäger, W., & Thalhammer, T. (2019). Future aspects for cannabinoids in breast cancer therapy. International Journal of Molecular Sciences, 20(7), 1673. 10.3390/ijms2007
   Web of Science ®Google Scholar
• Krieger, E., Joo, K., Lee, J., Lee, J., Raman, S., Thompson, J., Tyka, M., Baker, D., & Karplus, K. (2009). Improving physical realism, stereochemistry, and side-chain accuracy in homology modeling: Four approaches that performed well in CASP8. Proteins: Structure, Function, and Bioinformatics, 77(S9), 114–122. doi:10.1002/prot.22570
   PubMed Web of Science ®Google Scholar
• Kumar Mishra, N., & Raghava, G. P. S. (2011). Prediction of specificity and cross-reactivity of kinase inhibitors. Letters in Drug Design & Discovery, 8, 223–228. doi:10.2174/157018011794578204
   Web of Science ®Google Scholar
• Kuszewski, J., Gronenborn, A. M., & Clore, G. M. (1997). Improvements and extensions in the conformational database potential for the refinement of NMR and X-ray structures of proteins and nucleic acids. Journal of Magnetic Resonance, 125(1), 171–177. doi:10.1006/jmre.1997.1116
   PubMed Web of Science ®Google Scholar
• Laskowski, R. A., & Swindells, M. B. (2011). LigPlot+: Multiple ligand-protein interaction diagrams for drug discovery. Journal of Chemical Information and Modeling, 51(10), 2778–2786. doi:10.1021/ci200227u
   PubMed Web of Science ®Google Scholar
• Lill, M. A., & Danielson, M. L. (2011). Computer-aided drug design platform using PyMOL. Journal of Computer-Aided Molecular Design, 25(1), 13–19. doi:10.1007/s10822-010-9395-8
   PubMed Web of Science ®Google Scholar
• Lin, C.-H., Chuang, P.-Y., Chiang, C.-J., Lu, Y.-S., Cheng, A.-L., Kuo, W.-H., Huang, C.-S., Lai, M.-S., You, S.-L., & Tang, C.-H. (2014). Distinct clinicopathological features and prognosis of emerging young-female breast cancer in an East Asian country: A nationwide cancer registry-based study. The Oncologist, 19(6), 583–591. doi:10.1634/theoncologist.2014-0047
   PubMed Web of Science ®Google Scholar
• Liu, F.-C., Lin, H.-T., Kuo, C.-F., See, L.-C., Chiou, M.-J., & Yu, H.-P. (2017). Epidemiology and survival outcome of breast cancer in a nationwide study. Oncotarget,8(10),16939–16950. doi:10.18632/oncotarget.15207
   Google Scholar
• Lumachi, F., Brunello, A., Maruzzo, M., Basso, U., & Basso, S. M. M. (2013). Treatment of estrogen receptor-positive breast cancer. Current Medicinal Chemistry, 20(5), 596–604. doi:10.2174/092986713804999303
   PubMed Web of Science ®Google Scholar
• Morris, G. M., Ruth, H., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. J. (2009). Software news and updates AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30(16), 2785–2791. doi:10.1002/jcc.21256
   PubMed Web of Science ®Google Scholar
• Nir, I., Ayalon, D., Tsafriri, A., Cordova, T., & Lindner, H. R. (1973). Suppression of the cyclic surge of luteinizing hormone secretion and of ovulation in the Rat by Δ1-tetrahydrocannabinol. Nature, 243(5408), 470–471. doi:10.1038/243470a0
   PubMedGoogle Scholar
• Paruthiyil, S., Parmar, H., Kerekatte, V., Cunha, G. R., Firestone, G. L., & Leitman, D. C. (2004). Estrogen receptor β inhibits human breast cancer cell proliferation and tumor formation by causing a G2 cell cycle arrest. Cancer Research, 64(1), 423–428. doi:10.1158/0008-5472.CAN-03-2446
   PubMed Web of Science ®Google Scholar
• Paterni, I., Granchi, C., Katzenellenbogen, J. A., & Minutolo, F. (2014). Estrogen receptors alpha (ERα) and beta (ERβ): Subtype-selective ligands and clinical potential. Steroids, 90, 13–29. doi:10.1016/j.steroids.2014.06.012
   PubMed Web of Science ®Google Scholar
• PDQ Cancer Complementary and Alternative Medicine Editorial Board. (2019). Cannabis and Cannabinoids (PDQ ®) Health Professional Version, PDQ Cancer Information Summaries [Internet]. Bethesda (MD): National Cancer Institute (US); 2002-. Available from http://www.ncbi.nlm.nih.gov/books/NBK65755/ PubMed PMID: 26389198.
   Google Scholar
• Pettersen, E. F., Goddard, T. D., Huang, C. C., Couch, G. S., Greenblatt, D. M., Meng, E. C., & Ferrin, T. E. (2004). UCSF Chimera–A visualization system for exploratory research and analysis. Journal of Computational Chemistry, 25(13), 1605–1612. doi:10.1002/jcc.20084
   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. doi:10.1021/acs.jmedchem.5b00104
   PubMed Web of Science ®Google Scholar
• Sander, T. (2001). “OSIRIS property explorer.” Organic Chemistry Portal. http://www.organic-chemistry.org/prog/peo
   Google Scholar
• Sauer, M. A., Rifka, S. M., Hawks, R. L., Cutler, G. B., Jr., & Loriaux, D. L. (1983). Marijuana: Interaction with the estrogen receptor. Journal of Pharmacology and Experimental Therapeutics, 224(2), 404–407.
   Google Scholar
• Shiau, A. K., Barstad, D., Radek, J. T., Meyers, M. J., Nettles, K. W., Katzenellenbogen, B. S., Katzenellenbogen, J. A., Agard, D. A., & Greene, G. L. (2002). Structural characterization of a subtype-selective ligand reveals a novel mode of estrogen receptor antagonism. Nature Structural Biology, 9(5), 359-64. doi:10.1038/nsb787
   PubMedGoogle Scholar
• Sippl, M. J. (1993). Recognition of errors in three‐dimensional structures of proteins. Proteins: Structure, Function, and Genetics, 17(4), 355–362. doi:10.1002/prot.340170404
   PubMed Web of Science ®Google Scholar
• Takeda, S. (2014). Δ9-Tetrahydrocannabinol targeting estrogen receptor signaling: The possible mechanism of action coupled with endocrine disruption. Biological and Pharmaceutical Bulletin, 37, 1435–1438. 10.1248/bpb.b14-00226.
   PubMed Web of Science ®Google Scholar
• Takeda, S., Yoshida, K., Nishimura, H., Harada, M., Okajima, S., Miyoshi, H., Okamoto, Y., Amamoto, T., Watanabe, K., Omiecinski, C. J., & Aramaki, H. (2013). Δ9-tetrahydrocannabinol disrupts estrogen-signaling through up-regulation of estrogen receptor β (ERβ). Chemical Research in Toxicology, 26(7), 1073–1079. doi:10.1021/tx4000446
   PubMed Web of Science ®Google Scholar
• Thomas, C., & Åke Gustafsson, J. (2019). Estrogen receptor and breast cancer (pp. 309–342). In Zhang X. (Ed.), Estrogen Receptor and Breast Cancer. Cancer Drug Discovery and Development. Humana Press. doi:10.1007/978-3-319-99350-8.
   Google Scholar
• Tian, W., Chen, C., Lei, X., Zhao, J., & Liang, J. (2018). CASTp 3.0: Computed atlas of surface topography of proteins. Nucleic Acids Research, 46(W1), W363–W367. doi:10.1093/nar/gky473
   PubMed Web of Science ®Google Scholar
• Trott, O., & Olson, A. J. (2010). Software news and update 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. doi:10.1002/jcc.21334
   PubMed Web of Science ®Google Scholar
• Volkamer, A., Kuhn, D., Grombacher, T., Rippmann, F., & Rarey, M. (2012). Combining global and local measures for structure-based druggability predictions. Journal of Chemical Information and Modeling, 52(2), 360–372. doi:10.1021/ci200454v
   PubMed Web of Science ®Google Scholar
• Vriend, G., & Sander, C. (1993). Quality control of protein models: Directional atomic contact analysis. Journal of Applied Crystallography, 26(1), 47–60. doi:10.1107/S0021889892008240
   Web of Science ®Google Scholar
• Whyte, D. A., Al-Hammadi, S., Balhaj, G., Brown, O. M., Penefsky, H. S., & Souid, A. K. (2010). Cannabinoids inhibit cellular respiration of human oral cancer cells. Pharmacology, 85(6), 328–335. doi:10.1159/000312686
   PubMed Web of Science ®Google Scholar
• Yasmin-Karim, S., Moreau, M., Mueller, R., Sinha, N., Dabney, R., Herman, A., & Ngwa, W. (2018). Enhancing the therapeutic efficacy of cancer treatment with cannabinoids. Frontiers in Oncology, 8, 4–11. doi:10.3389/fonc.2018.00114
   PubMed Web of Science ®Google Scholar