Discovery of potential HER2 inhibitors from Mangifera indica for the treatment of HER2-Positive breast cancer: an integrated computational approach

References

• Adelakun, N., Obaseki, I., Adeniyi, A., Fapohunda, O., Obaseki, E., & Omotuyi, O. (2020). Discovery of new promising USP14 inhibitors: Computational evaluation of the thumb-palm pocket. Journal of Biomolecular Structure & Dynamics, 1–11. https://doi.org/10.1080/07391102.2020.1844803
   Google Scholar
• Aderibigbe, A. O., Emudianughe, T. S., & Lawal, B. A. (2001). Evaluation of the antidiabetic action of Mangifera indica in mice. Phytotherapy Research: PTR, 15(5), 456–458. https://doi.org/10.1002/ptr.859
   PubMed Web of Science ®Google Scholar
• Andreas, S., Wieland, U., & Reinhold, C. (2000). Characterization of polyphenols in mango puree concentrate by HPLC with diode array and mass spectrometric detection. International Journal of Food Science and Nutrition, 1, 161–166.
   Google Scholar
• Arcila, M. E., Chaft, J. E., Nafa, K., Roy-Chowdhuri, S., Lau, C., Zaidinski, M., Paik, P. K., Zakowski, M. F., Kris, M. G., & Ladanyi, M. (2012). Prevalence, clinicopathologic associations, and molecular spectrum of ERBB2 (HER2) tyrosine kinase mutations in lung adenocarcinomas. Clinical Cancer Research, 18(18), 4910–4918. https://doi.org/10.1158/1078-0432.CCR-12-0912
   PubMed Web of Science ®Google Scholar
• Avjani, K. T., Gajjar, A. K., & Savjani, J. K. (2012). Drug solubility: Importance and enhancement techniques. ISRN Pharmaceutics, 2012, 195727. https://doi.org/10.5402/2012/195727
   PubMedGoogle Scholar
• Balasubramanian, R., Rolph, R., Morgan, C., & Hamed, H. (2019). Genetics of breast cancer: Management strategies and risk-reducing surgery. British Journal of Hospital Medicine, 80(12), 720–725. https://doi.org/10.12968/hmed.2019.80.12.720
   Web of Science ®Google Scholar
• Balogun, T. A., Buliaminu, K. D., Chukwudozie, O. S., Tiamiyu, Z. A., & Idowu, J. T. (2021). Anticancer potential of Moringa oleifera on BRCA-1 gene: Systems biology. Bioinformatics and Biology Insights, 15, 117793222110107. https://doi.org/10.1177/11779322211010703
   Google Scholar
• Baselga, J., Coleman, R. E., Cortés, J., & Janni, W. (2017). Advances in the management of HER2-positive early breast cancer. Critical Reviews in Oncology/Hematology, 119, 113–122. https://doi.org/10.1016/j.critrevonc.2017.10.001
   PubMed Web of Science ®Google Scholar
• Benet, L. Z., Hosey, C. M., Ursu, O., & Oprea, T. I. (2016). BDDCS, the Rule of 5 and drugability. Advanced Drug Delivery Reviews, 101, 89–98. https://doi.org/10.1016/j.addr.2016.05.007
   PubMed Web of Science ®Google Scholar
• Bowers, K. J., Chow, D. E., Xu, H., Dror, R. O., Eastwood, M. P., Gregersen, B. A., Klepeis, J. L., Kolossvary, I., Moraes, M. A., Sacerdoti, F. D., & Shaw, D. E. (2006). Scalable algorithms for molecular dynamics simulations on commodity clusters. In Proceedings of the 2006 ACM/IEEE Conference on Supercomputing (p. 43-43).https://doi.org/10.1109/SC.2006
   Google Scholar
• Chan, A., Moy, B., Mansi, J., Ejlertsen, B., Holmes, F. A., Chia, S., Iwata, H., Gnant, M., Loibl, S., Barrios, C. H., Somali, I., Smichkoska, S., Martinez, N., Alonso, M. G., Link, J. S., Mayer, I. A., Cold, S., Murillo, S. M., Senecal, F., Inoue, K., … Martin, M., ExteNET Study Group. (2021). Final efficacy results of neratinib in HER2-positive hormone receptor-positive early-stage breast cancer from the phase III ExteNET trial. Clinical Breast Cancer, 21(1), 80–91.e7. https://doi.org/10.1016/j.clbc.2020.09.014
   PubMed Web of Science ®Google Scholar
• Cheng, F., Li, W., Zhou, Y., Shen, J., Wu, Z., Liu, G., Lee, P. W., & Tang, Y. (2012). admetSAR: a comprehensive source and free tool for assessment of chemical ADMET properties. Journal of Chemical Information and Modeling, 52(11), 3099–3099e3105. https://doi.org/10.1021/ci300367a
   PubMed Web of Science ®Google Scholar
• Cheng, P., Peng, Z-g., Yang, J., & Song, S-j. (2007). The effect of mangiferin on telomerase activity and apoptosis in leukemic K562 cells. Zhong Yao Cai = Zhongyaocai = Journal of Chinese Medicinal Materials, 30(3), 306–309.
   PubMedGoogle Scholar
• Cragg, G. M., & Newman, D. J. (2005). Plants as a source of anti-cancer agents. Journal of Ethnopharmacology, 100(1-2), 72–79. https://doi.org/10.1016/j.jep.2005.05.011
   PubMed Web of Science ®Google Scholar
• Das, S. K., Mahanta, S., Tanti, B., Tag, H., & Hui, P. K. (2021). Identification of phytocompounds from Houttuynia cordata Thunb. as potential inhibitors for SARS-CoV-2 replication proteins through GC-MS/LC-MS characterization, molecular docking and molecular dynamics simulation. Molecular Diversity, 7, 1–24. https://doi.org/10.1007/s11030-021-10226-2
   Google Scholar
• Doi, T., Takiuchi, H., Ohtsu, A., Fuse, N., Goto, M., Yoshida, M., Dote, N., Kuze, Y., Jinno, F., Fujimoto, M., Takubo, T., Nakayama, N., & Tsutsumi, R. (2012). Phase I first-in-human study of TAK-285, a novel investigational dual HER2/EGFR inhibitor, in cancer patients . British Journal of Cancer, 106(4), 666–672. https://doi.org/10.1038/bjc.2011.590
   PubMed Web of Science ®Google Scholar
• Ferlay, J., Ervik, M., Lam, F., Colombet, M., Mery, L., & Piñeros, M. (2020). Global cancer observatory: Cancer today. Lyon: International Agency for Research on Cancer; https://gco.iarc.fr/today.
   Google Scholar
• Friesner, R. A., Murphy, R. B., Repasky, M. P., Frye, L. L., Greenwood, J. R., Halgren, T. A., Sanschagrin, P. C., & Mainz, D. T. (2006). Extra precision glide: Docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes. Journal of Medicinal Chemistry, 49(21), 6177–6196. https://doi.org/10.1021/jm051256o
   PubMed Web of Science ®Google Scholar
• GraphPad Prism. (2019). GraphPad software. Retrieved September 30, 2019, from www.graphpad.com.
   Google Scholar
• Guarneri, V., Lenihan, D. J., Valero, V., Durand, J. B., Broglio, K., Hess, K. R., Michaud, L. B., Gonzalez-Angulo, A. M., Hortobagyi, G. N., & Esteva, F. J. (2006). Long-term cardiac tolerability of trastuzumab in metastatic breast cancer: The M.D. Anderson cancer center experience. Journal of Clinical Oncology : official Journal of the American Society of Clinical Oncology, 24(25), 4107–4115. https://doi.org/10.1200/JCO.2005.04.9551
   PubMed Web of Science ®Google Scholar
• Guo, Y., Zhi, F., Chen, P., Zhao, K., Xiang, H., Mao, Q., Wang, X., & Zhang, X. (2017). Green tea and the risk of prostate cancer: A systematic review and meta-analysis. Medicine, 96(13), e6426. https://doi.org/10.1097/MD.0000000000006426
   PubMed Web of Science ®Google Scholar
• Holbro, T., Civenni, G., & Hynes, N. E. (2003). The ErbB receptors and their role in cancer progression. Experimental Cell Research, 284(1), 99–110. https://doi.org/10.1016/s0014-4827(02)00099-x
   PubMed Web of Science ®Google Scholar
• Hudis, C. A. (2007). Trastuzumab-mechanism of action and use in clinical practice. The New England Journal of Medicine, 357(1), 39–51. doi:10.1056/NEJMra043186
   PubMed Web of Science ®Google Scholar
• Ishikawa, T., Seto, M., Banno, H., Kawakita, Y., Oorui, M., Taniguchi, T., Ohta, Y., Tamura, T., Nakayama, A., Miki, H., Kamiguchi, H., Tanaka, T., Habuka, N., Sogabe, S., Yano, J., Aertgeerts, K., & Kamiyama, K. (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. https://doi.org/10.1021/jm2008634.
   PubMed Web of Science ®Google Scholar
• Jacobson, M. P., Pincus, D. L., Rapp, C. S., Day, T. J. F., Honig, B., Shaw, D. E., & Friesner, R. A. (2004). A hierarchical approach to all-atom protein loop prediction. Proteins, 55(2), 351–367. https://doi.org/10.1002/prot.10613
   PubMed Web of Science ®Google Scholar
• Jemal, A., Siegel, R., Ward, E., Murray, T., Xu, J., Smigal, C., & Thun, M. J. (2006). Cancer statistics, 2006. CA: A Cancer Journal for Clinicians, 56(2), 106–130. https://doi.org/10.3322/canjclin.56.2.106
   PubMed Web of Science ®Google Scholar
• Kamchonwongpaisan, S., Quarrell, R., Charoensetakul, N., Ponsinet, R., Vilaivan, T., Vanichtanankul, J., Tarnchompoo, B., Sirawaraporn, W., Lowe, G., & Yuthavong, Y. (2004). Inhibitors of multiple mutants of Plasmodium falciparum dihydrofolate reductase and their antimalarial activities. Journal of Medicinal Chemistry, 47(3), 673–680. https://doi.org/10.1021/jm030165t
   PubMed Web of Science ®Google Scholar
• Khurana, R. K., Kaur, R., Lohan, S., Kamalinder, K. S., & Singh, B. (2016). Mangiferin: A promising anticancer bioactive. Pharmaceutical Patent Analyst, 5(3), 169–181. https://doi.org/10.4155/ppa-2016-0003
   PubMed Web of Science ®Google Scholar
• Klapper, L. N., Kirschbaum, M. H., Sela, M., & Yarden, Y. (2000). Biochemical and clinical implications of the ErbB/HER signaling network of growth factor receptors. Advances in Cancer Research, 77, 25–79.
   PubMed Web of Science ®Google Scholar
• Lamothe, S. M., Guo, J., Li, W., Yang, T., & Zhang, S. (2016). The human ether-a-go-go-related Gene (hERG) potassium channel represents an unusual target for protease-mediated damage. The Journal of Biological Chemistry, 291(39), 20387–20401. https://doi.org/10.1074/jbc.M116.743138
   PubMed Web of Science ®Google Scholar
• Li, H., Huang, J., Yang, B., Xiang, T., Yin, X., Peng, W., Cheng, W., Wan, J., Luo, F., Li, H., & Ren, G. (2013). Mangiferin exerts antitumor activity in breast cancer cells by regulating matrix metalloproteinases, epithelial to mesenchymal transition, and β-catenin signaling pathway. Toxicology and Applied Pharmacology, 272(1), 180–190. https://doi.org/10.1016/j.taap.2013.05.011
   PubMed Web of Science ®Google Scholar
• Lin, J. P., Yang, J. S., Lin, J. J., Lai, K. C., Lu, H. F., Ma, C. Y., Sai-Chuen Wu, R., Wu, K. C., Chueh, F. S., Gibson Wood, W., & Chung, J. G. (2012). Rutin inhibits human leukemia tumor growth in a murine xenograft model in vivo. Environmental Toxicology, 27(8), 480–484. https://doi.org/10.1002/tox.20662
   PubMed Web of Science ®Google Scholar
• Maestro. (2018). Maestro. Schrödinger, LLC.
   Google Scholar
• Martin, M., Bonneterre, J., Geyer, C. E., Ito, Y., Ro, J., Lang, I., Kim, S.-B., Germa, C., Vermette, J., Wang, K., Wang, K., & Awada, A. Jr. (2013). A phase two randomized trial of neratinib monotherapy versus lapatinib plus capecitabine combination therapy in patients with HER2+ advanced breast cancer. European Journal of Cancer, 49(18), 3763–3772. https://doi.org/10.1016/j.ejca.2013.07.142
   PubMed Web of Science ®Google Scholar
• Martínez, M. T., Pérez-Fidalgo, J. A., Martín-Martorell, P., Cejalvo, J. M., Pons, V., Bermejo, B., Martín, M., Albanell, J., & Lluch, A. (2016). Treatment of HER2 positive advanced breast cancer with T-DM1: A review of the literature. Critical Reviews in Oncology/Hematology, 97, 96–106. https://doi.org/10.1016/j.critrevonc.2015.08.011
   PubMed Web of Science ®Google Scholar
• Martyna, G. J., Tobias, D. J., & Klein, M. L. (1994). Constant pressure molecular dynamics algorithms. The Journal of Chemical Physics, 101(5), 4177–4189. https://doi.org/10.1063/1.467468
   Web of Science ®Google Scholar
• McDonnell, A. M., & Dang, C. H. (2013). Basic review of the cytochrome p450 system. Journal of the Advanced Practitioner in Oncology, 4(4), 263–268. https://doi.org/10.6004/jadpro.2013.4.4.7
   PubMedGoogle Scholar
• McGuire, A., Brown, J. A., Malone, C., McLaughlin, R., & Kerin, M. J. (2015). Effects of age on the detection and management of breast cancer. Cancers, 7 (2), 908–929. https://doi.org/10.3390/cancers7020815
   PubMed Web of Science ®Google Scholar
• Moasser, M. M. (2007). The oncogene HER2: Its signaling and transforming functions and its role in human cancer pathogenesis. Oncogene, 26(45), 6469–6487. https://doi.org/10.1038/sj.onc.1210477
   PubMed Web of Science ®Google Scholar
• Mortelmans, K., & Zeiger, E. (2000). The Ames Salmonella/microsome mutagenicity assay. Mutation Research, 455(1–2), 29–60. https://doi.org/10.1016/S0027-5107(00)00064-6
   PubMed Web of Science ®Google Scholar
• Nagata, Y., Lan, K.-H., Zhou, X., Tan, M., Esteva, F. J., Sahin, A. A., Klos, K. S., Li, P., Monia, B. P., Nguyen, N. T., Hortobagyi, G. N., Hung, M.-C., & Yu, D. (2004). PTEN activation contributes to tumor inhibition by trastuzumab, and loss of PTEN predicts trastuzumab resistance in patients. Cancer Cell, 6(2), 117–127. https://doi.org/10.1016/j.ccr.2004.06.022
   PubMed Web of Science ®Google Scholar
• Natasha, T. R., Zora, K., & Dragica, N. V. (2006). Cross-talk between ER and Her 2 in breast carcinoma. Arch Oncology, 14, 146–150.
   Google Scholar
• Newman, D. J., Cragg, G. M., & Snader, K. M. (2003). Natural products as sources of new drugs over the period 1981–2002. Journal of Natural Products, 66(7), 1022–1037. https://doi.org/10.1021/np030096
   PubMed Web of Science ®Google Scholar
• Núñez Sellés, A. J., Vélez Castro, H. T., Agüero-Agüero, J., González-González, J., Naddeo, F., De Simone, F., & Rastrelli, L. (2002). Isolation and quantitative analysis of phenolic antioxidants, free sugars, and polyols from Mango (Mangifera indica L.) stem bark aqueous decoction used in Cuba as a nutritional supplement. Journal of Agricultural and Food Chemistry, 50(4), 762–766.
   PubMed Web of Science ®Google Scholar
• Ornelas-Paz, J. d J., Yahia, E. M., & Gardea-Bejar, A. (2007). Identification and quantification of xanthophyll esters, carotenes, and tocopherols in the fruit of seven Mexican mango cultivars by liquid chromatography-atmospheric pressure chemical ionization-time-of-flight mass spectrometry [LC-(APcI(+))-MS. Journal of Agricultural and Food Chemistry, 55(16), 6628–6635. https://doi.org/10.1021/jf0706981
   PubMed Web of Science ®Google Scholar
• Peng, Z. G., Yao, Y. B., Yang, J., Tang, Y. L., & Huang, X. (2015). Mangiferin induces cell cycle arrest at G2/M phase through ATR-Chk1 pathway in HL-60 leukemia cells. Genetics and Molecular Research: GMR, 14(2), 4989–5002.
   PubMed Web of Science ®Google Scholar
• Pott, I., Marx, M., Neidhart, S., Mühlbauer, W., & Carle, R. (2003). Quantitative determination of beta-carotene stereoisomers in fresh, dried, and solar-dried mangoes (Mangifera indica L.). Journal of Agricultural and Food Chemistry, 51(16), 4527–4531. https://doi.org/10.1021/jf034084h
   PubMed Web of Science ®Google Scholar
• Prime. (2019). Prime. Schrödinger, LLC.
   Google Scholar
• Rodríguez, J., Di Pierro, D., Gioia, M., Monaco, S., Delgado, R., Coletta, M., & Marini, S. (2006). Effects of a natural extract from Mangifera indica L, and its active compound, mangiferin, on energy state and lipid peroxidation of red blood cells. Biochimica et Biophysica Acta, 1760(9), 1333–1342. https://doi.org/10.1016/j.bbagen.2006.04.005
   PubMed Web of Science ®Google Scholar
• Roos, K., Wu, C., Damm, W., Reboul, M., Stevenson, J. M., Lu, C., Dahlgren, M. K., Mondal, S., Chen, W., Wang, L., Abel, R., Friesner, R. A., & Harder, E. D. (2019). OPLS3e: Extending force field coverage for drug-like small molecules. Journal of Chemical Theory and Computation, 15(3), 1863–1874. https://doi.org/10.1021/acs.jctc.8b01026
   PubMed Web of Science ®Google Scholar
• Saini, K. S., Azim, H. A., Jr, Metzger-Filho, O., Loi, S., Sotiriou, C., Azambuja, E., & Piccart, M. (2011). Beyond trastuzumab: New treatment options for HER2-positive breast cancer. Breast (Edinburgh, Scotland), 20(Suppl. 3), S20–S27. https://doi.org/10.1016/S0960-9776(11)70289-2
   PubMed Web of Science ®Google Scholar
• Sastry, G. M., Adzhigirey, M., Day, T., Annabhimoju, R., & Sherman, W. (2013). Protein and ligand preparation: Parameters, protocols, and influence on virtual screening enrichments. Journal of Computer-Aided Molecular Design, 27(3), 221–234. https://doi.org/10.1007/s10822-013-9644-8
   PubMed Web of Science ®Google Scholar
• Scaltriti, M., & Baselga, J. (2006). The epidermal growth factor receptor pathway: A model for targeted therapy. Clinical Cancer Research: An Official Journal of the American Association for Cancer Research, 12(18), 5268–5272. https://doi.org/10.1158/1078-0432.CCR-05-1554
   PubMed Web of Science ®Google Scholar
• Schrödinger. (2018). Maestro-desmond interoperability tools. Schrödinger.
   Google Scholar
• Shelley, J. C., Cholleti, A., Frye, L. L., Greenwood, J. R., Timlin, M. R., & Uchimaya, M. (2007). Epik: A software program for pK(a) prediction and protonation state generation for drug-like molecules. Journal of Computer-Aided Molecular Design, 21(12), 681–691. https://doi.org/10.1007/s10822-007-9133-z
   PubMed Web of Science ®Google Scholar
• Smith, D., Di, L., & Kerns, E. (2010). The effect of plasma protein binding on in vivo efficacy: Misconceptions in drug discovery. Nature Reviews. Drug Discovery, 9(12), 929–939. https://doi.org/10.1038/nrd3287
   PubMed Web of Science ®Google Scholar
• Swain, S. M., Baselga, J., Kim, S.-B., Ro, J., Semiglazov, V., Campone, M., Ciruelos, E., Ferrero, J.-M., Schneeweiss, A., Heeson, S., Clark, E., Ross, G., Benyunes, M. C., & Cortés, J. (2015). Pertuzumab, trastuzumab, and docetaxel in HER2-positive metastatic breast cancer. New England Journal of Medicine, 372(8), 724–734. a1413513 https://doi.org/10.1056/NEJMo
   PubMed Web of Science ®Google Scholar
• Tai, W., Mahato, R., & Cheng, K. (2010). The role of HER2 in cancer therapy and targeted drug delivery. Journal of Controlled Release: Official Journal of the Controlled Release Society, 146(3), 264–275. https://doi.org/10.1016/j.jconrel.2010.04.009
   PubMed Web of Science ®Google Scholar
• Walum, E. (1998). Acute oral toxicity. Environmental Health Perspectives, 106(Suppl. 2), 497–503. ):https://doi.org/10.1289/ehp.98106497
   PubMed Web of Science ®Google Scholar
• Wanat, K. (2020). Biological barriers, and the influence of protein binding on the passage of drugs across them. Molecular Biology Reports, 47(4), 3221–3231. https://doi.org/10.1007/s11033-020-05361-2
   PubMed Web of Science ®Google Scholar
• Weis, A., Katebzadeh, K., Soderhjelm, P., Nilsson, I., & Ryde, U. (2006). Ligand affinities predicted with the MM/PBSA method: Dependence on the simulation method and the force field. Journal of Medicinal Chemistry, 49(22), 6596–6606. https://doi.org/10.1021/jm0608210
   PubMed Web of Science ®Google Scholar
• World Health Organization (WHO). (2021). A report about cancer. Retrieved from https://www.who.int/news-room/fact-sheets/detail/cancer
   Google Scholar
• Xu, Z., Zhang, Y., Li, N., Liu, P., Gao, L., Gao, X., & Tie, X. (2017). Efficacy and safety of lapatinib and trastuzumab for HER2-positive breast cancer: A systematic review and meta-analysis of randomised controlled trials. BMJ Open, 7(3), e013053. https://doi.org/10.1136/bmjopen-2016-013053
   PubMed Web of Science ®Google Scholar
• Yang, H., Lou, C., Sun, L., Li, J., Cai, Y., Wang, Z., Li, W., Liu, G., & Tang, Y. (2019). admetSAR 2.0: Web-service for prediction and optimization of chemical ADMET properties. Bioinformatics (Oxford, England), 35(6), 1067–1069. https://doi.org/10.1093/bioinformatics/bty707
   PubMed Web of Science ®Google Scholar
• Yarden, Y. (2001). Biology of HER2 and its importance in breast cancer. Oncology, 61(Suppl. 2), 1–13. https://doi.org/10.1159/000055396
   PubMed Web of Science ®Google Scholar
• Yousuf, Z., Iman, K., Iftikhar, N., & Mirza, M. U. (2017). Structure-based virtual screening and molecular docking for the identification of potential multi-targeted inhibitors against breast cancer. Breast Cancer (Dove Medical Press), 9, 447–459. https://doi.org/10.2147/BCTT.S132074
   PubMed Web of Science ®Google Scholar
• Zhang, B. P., Zhao, J., Li, S. S., Yang, L. J., Zeng, L. L., Chen, Y., & Fang, J. (2014). Mangiferin activates Nrf2-antioxidant response element signaling without reducing the sensitivity to etoposide of human myeloid leukemia cells in vitro. Acta Pharmacologica Sinica, 35(2), 257–266. https://doi.org/10.1038/aps.2013.165
   PubMed Web of Science ®Google Scholar
• Zhao, J., Zhang, B., Li, S., Zeng, L., Chen, Y., & Fang, J. (2014). Mangiferin increases Nrf2 protein stability by inhibiting its ubiquitination and degradation in human HL60 myeloid leukemia cells. International Journal of Molecular Medicine, 33(5), 1348–1354. https://doi.org/10.3892/ijmm.2014.1696
   PubMed Web of Science ®Google Scholar