FMS-like tyrosine kinase-3 (FLT3) inhibitors with better binding affinity and ADMET properties than sorafenib and gilteritinib against acute myeloid leukemia: in silico studies

References

• American Physiological Society. (2019). FMS-like tyrosine kinase 3/FLT3: From basic science to clinical implications. https://journals.physiology.org/doi/full/10.1152/physrev.00029.2018. https://doi.org/10.1152/physrev.00029.2018
   Google Scholar
• Aqil, F., Munagala, R., Jeyabalan, J., & Vadhanam, M. V. (2013). Bioavailability of phytochemicals and its enhancement by drug delivery systems. Cancer Letters, 334(1), 133–141. https://doi.org/10.1016/j.canlet.2013.02.032
   PubMed Web of Science ®Google Scholar
• Arber, D. A., Orazi, A., Hasserjian, R., Thiele, J., Borowitz, M. J., Le Beau, M. M., Bloomfield, C. D., Cazzola, M., & Vardiman, J. W. (2016). The 2016 revision to the World Health Organization classification of myeloid neoplasms and acute leukemia. Blood, 127(20), 2391–2405. https://doi.org/10.1182/blood-2016-03-643544
   PubMed Web of Science ®Google Scholar
• Basilico, S., & Göttgens, B. (2017). Dysregulation of haematopoietic stem cell regulatory programs in acute myeloid leukaemia. Journal of Molecular Medicine (Berlin, Germany), 95(7), 719–727. https://doi.org/10.1007/s00109-017-1535-3
   PubMed Web of Science ®Google Scholar
• Berenstein, R. (2015). Class III receptor tyrosine kinases in acute leukemia - Biological functions and modern laboratory analysis. Biomarker Insights, 10(Suppl 3), 1–14. https://doi.org/10.4137/BMI.S22433
   PubMedGoogle Scholar
• Birbrair, A., Frenette, P. S. (2016, 1 March). Niche heterogeneity in the bone marrow. Annals of the New York Academy of Sciences, 1370 (1), 82–96. https://doi.org/10.1111/nyas.13016
   PubMedGoogle Scholar
• Cancer.Net. (2020). Leukemia - Acute myeloid - AML: Statistics. https://www.cancer.net/cancer-types/leukemia-acute-myeloid-aml/statistics.
   Google Scholar
• Choudhary, M. I., Shaikh, M., Tul-Wahab, A., & Ur-Rahman, A. (2020). In silico identification of potential inhibitors of key SARS-CoV-2 3CL hydrolase (Mpro) via molecular docking, MMGBSA predictive binding energy calculations, and molecular dynamics simulation. PloS One, 15(7), e0235030. https://doi.org/10.1371/journal.pone.0235030
   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), 1–13. https://doi.org/10.1038/srep42717
   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, 42717. https://doi.org/10.1038/srep42717 PMID: 28256516; PMCID: PMC5335600.
   PubMed Web of Science ®Google Scholar
• Dallakyan, S., & Olson, A. J. (2015). Small-molecule library screening by docking with PyRx. Methods in Molecular Biology (Clifton, N.J.), 1263, 243–250. https://doi.org/10.1007/978-1-4939-2269-7_19 PMID: 25618350.
   PubMedGoogle Scholar
• Daver, N., Schlenk, R. F., Russell, N. H., & Levis, M. J. (2019). Targeting FLT3 mutations in AML: Review of current knowledge and evidence. Leukemia, 33(2), 299–312. ‐https://doi.org/10.1038/s41375-018-0357-9
   PubMed Web of Science ®Google Scholar
• Diseases, N., Grewal, A. S., Bhardwaj, S., Pandita, D., Lather, V., & Singh Sekhon, B. (2015). Updates on aldose reductase inhibitors for management of diabetic complications and non-diabetic diseases. Mini Reviews in Medicinal Chemistry, 16(2), 120–162. https://doi.org/10.2174/1389557515666150909143737
   Web of Science ®Google Scholar
• Döhner, H., Weisdorf, D. J., & Bloomfield, C. D. (2015). Acute myeloid leukemia. The New England Journal of Medicine, 373(12), 1136–1152. https://doi.org/10.1056/NEJMra1406184
   PubMed Web of Science ®Google Scholar
• Elyamany, G., Awad, M., Fadalla, K., Albalawi, M., Al Shahrani, M., & Al Abdulaaly, A. (2014). Frequency and prognostic relevance of FLT3 mutations in Saudi acute myeloid leukemia patients. Advances in Hematology, 2014, 141360. https://doi.org/10.1155/2014/141360
   PubMedGoogle Scholar
• Erukainure, O. L., Mopuri, R., Chukwuma, C. I., Koorbanally, N. A., & Islam, M. S. (2018). Phaseolus lunatus (lima beans) abates Fe2+‐induced hepatic redox imbalance; inhibits intestinal glucose absorption and major carbohydrate catabolic enzymes; and modulates muscle glucose uptake. Journal of Food Biochemistry, 42(6), 1–14. https://doi.org/10.1111/jfbc.12655
   Web of Science ®Google Scholar
• Fernandes, Í. A., Braga Resende, D., Ramalho, T. C., Kuca, K., & da Cunha, E. F. F. (2020). Theoretical studies aimed at finding FLT3 inhibitors and a promising compound and molecular pattern with dual aurora B/FLT3 activity. Molecules, 25(7), 1726. https://doi.org/10.3390/molecules25071726
   PubMed Web of Science ®Google Scholar
• Gao, N., Cheng, S., Budhraja, A., Gao, Z., Chen, J., Liu, E. H., Huang, C., Chen, D., Yang, Z., Liu, Q., Li, P., Shi, X., & Zhang, Z. (2012). Ursolic acid induces apoptosis in human leukaemia cells and exhibits anti-leukaemic activity in nude mice through the PKB pathway. British Journal of Pharmacology, 165(6), 1813–1826. https://doi.org/10.1111/j.1476-5381.2011.01684.x
   PubMed Web of Science ®Google Scholar
• Ghose, A. K., Viswanadhan, V. N., & Wendoloski, J. J. (January, 1999). A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. Journal of Combinatorial Chemistry, 1 (1), 55–68. https://doi.org/10.1021/cc9800071
   PubMedGoogle Scholar
• Gilliland, D. G., & Griffin, J. D. (2002). Role of FLT3 in leukemia. Current Opinion in Hematology, 9(4), 274–281. https://doi.org/10.1097/00062752-200207000-00003 PMID: 12042700.
   PubMed Web of Science ®Google Scholar
• Gokhale, P., Chauhan, A., Arora, A., Khandekar, N., Nayarisseri, A., & Singh, S. K. (2019). FLT3 inhibitor design using molecular docking based virtual screening for acute myeloid leukemia. Bioinformation, 15(2), 104–115. https://doi.org/10.6026/97320630015104
   PubMed Web of Science ®Google Scholar
• Grafone, T., Palmisano, M., Nicci, C., & Storti, S. (2012). An overview on the role of FLT3-tyrosine kinase receptor in acute myeloid leukemia: Biology and treatment. Oncology Reviews, 6(1), e8. https://doi.org/10.4081/oncol.2012.e8 PMID: 25992210; PMCID: PMC4419636.
   PubMedGoogle Scholar
• Grgić, J., Šelo, G., Planinić, M., Tišma, M., & Bucić-Kojić, A. (2020). Role of the encapsulation in bioavailability of phenolic compounds. Antioxidants (Basel), 9(10), 923. https://doi.org/10.3390/antiox9100923 PMID: 32993196; PMCID: PMC7601682.
   PubMedGoogle Scholar
• Guan, L., Yang, H., Cai, Y., Sun, L., Di, P., Li, W., Liu, G., & Tang, Y. (2019). ADMET-score - a comprehensive scoring function for evaluation of chemical drug-likeness. MedChemComm, 10(1), 148–157. https://doi.org/10.1039/c8md00472b
   PubMed Web of Science ®Google Scholar
• Guha, R. (2013). On exploring structure-activity relationships. Methods in Molecular Biology (Clifton, N.J.), 993, 81–94. https://doi.org/10.1007/978-1-62703-342-8_6.
   PubMedGoogle Scholar
• Guimarães, A. P., Oliveira, A. A., da Cunha, E. F. F., Ramalho, T. C., & França, T. C. C. (2011). Design of new chemotherapeutics against the deadly anthrax disease. Docking and molecular dynamics studies of inhibitors containing pyrrolidine and riboamidrazone rings on nucleoside hydrolase from Bacillus anthracis. Journal of Biomolecular Structure & Dynamics, 28(4), 455–469. https://doi.org/10.1080/07391102.2011.10508588
   PubMed Web of Science ®Google Scholar
• Hanh, H., Tran, T., Nguyen, M. C., Le, H. T., Nguyen, T. L., & Pham, T. B. (2013). Inhibitors of a -glucosidase and a -amylase from Cyperus rotundus. Pharmaceutical Biology, 52(1), 74–77. https://doi.org/10.3109/13880209.2013.814692
   PubMed Web of Science ®Google Scholar
• Hayashi, H., Hattori, S., Inoue, K., Khodzhimatov, O., Ashurmetov, O., Ito, M., & Honda, G. (2003). Field survey of Glycyrrhiza plants in Central Asia (3). Chemical characterization of G. glabra collected in Uzbekistan. Chemical & Pharmaceutical Bulletin, 51(11), 1338–1340. https://doi.org/10.1248/cpb.51.1338
   PubMed Web of Science ®Google Scholar
• Huang, H.-L., Hsieh, M.-J., Chien, M.-H., Chen, H.-Y., Yang, S.-F., & Hsiao, P.-C. (2014). Glabridin mediate caspases activation and induces apoptosis through JNK1/2 and p38 MAPK pathway in human promyelocytic leukemia cells. PLoS One, 9(6), e98943. https://doi.org/10.1371/journal.pone.0098943
   PubMed Web of Science ®Google Scholar
• Jagannathan-Bogdan, M., & Zon, L. I. (2013). Hematopoiesis. Development (Cambridge, England), 140(12), 2463–2467. https://doi.org/10.1242/dev.083147
   PubMed Web of Science ®Google Scholar
• Jia, C.-Y., Li, J.-Y., Hao, G.-F., & Yang, G.-F. (2020). A drug-likeness toolbox facilitates ADMET study in drug discovery. Drug Discovery Today, 25(1), 248–258. https://doi.org/10.1016/j.drudis.2019.10.014
   PubMed Web of Science ®Google Scholar
• Kawase, T., Nakazawa, T., Eguchi, T., Tsuzuki, H., Ueno, Y., Amano, Y., Suzuki, T., Mori, M., & Yoshida, T. (2019). Effect of Fms-like tyrosine kinase 3 (FLT3) ligand (FL) on antitumor activity of gilteritinib, a FLT3 inhibitor, in mice xenografted with FL-overexpressing cells. Oncotarget, 10(58), 6111–6123. https://doi.org/10.18632/oncotarget.27222
   PubMedGoogle Scholar
• Kiyoi, H., Kawashima, N., & Ishikawa, Y. (2020). FLT3 mutations in acute myeloid leukemia: Therapeutic paradigm beyond inhibitor development. Cancer Science, 111(2), 312–322. https://doi.org/10.1111/cas.14274
   PubMed Web of Science ®Google Scholar
• Kottaridis, P. D., Gale, R. E., & Linch, D. C. (2003). Flt3 mutations and leukaemia. British Journal of Haematology, 122(4), 523–538. https://doi.org/10.1046/j.1365-2141.2003.04500.x
   PubMed Web of Science ®Google Scholar
• Kuete, V., Mbaveng, A. T., Zeino, M., Fozing, C. D., Ngameni, B., Kapche, G. D., Ngadjui, B. T., & Efferth, T. (2015). Cytotoxicity of three naturally occurring flavonoid derived compounds (artocarpesin, cycloartocarpesin and isobavachalcone) towards multi-factorial drug-resistant cancer cells. Phytomedicine: International Journal of Phytotherapy and Phytopharmacology, 22(12), 1096–1102. https://doi.org/10.1016/j.phymed.2015.07.006 PMID: 26547532.
   PubMed Web of Science ®Google Scholar
• Lee, K. T., Kim, J. I., Rho, Y. S., Chang, S. G., Jung, J. C., Park, J. H., Park, H. J., & Miyamoto, K. (1999). Hypericin induces both differentiation and apoptosis in human promyelocytic leukemia HL-60 cells. Biological & Pharmaceutical Bulletin, 22(12), 1271–1274. Dechttps://doi.org/10.1248/bpb.22.1271 PMID: 10746153.
   PubMed Web of Science ®Google Scholar
• Levis, M. (2013). FLT3 mutations in acute myeloid leukemia: What is the best approach in 2013? Hematology. American Society of Hematology. Education Program, 2013, 220–226.
   PubMed Web of Science ®Google Scholar
• Li, R. F., Feng, Y. Q., Chen, J. H., Ge, L. T., Xiao, S. Y., & Zuo, X. L. (2015). Naringenin suppresses K562 human leukemia cell proliferation and ameliorates adriamycin-induced oxidative damage in polymorphonuclear leukocytes. Experimental and Therapeutic Medicine, 9(3), 697–706. https://doi.org/10.3892/etm.2015.2185
   PubMed Web of Science ®Google Scholar
• Lin, Z., Jiang, J., & Liu, X. S. (2016). Ursolic acid-mediated apoptosis of K562 cells involves Stat5/Akt pathway inhibition through the induction of Gfi-1. Scientific Reports, 6, 33358. https://doi.org/10.1038/srep33358
   PubMed Web of Science ®Google Scholar
• Lipinski, C. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (2001, March). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 46 (1-3), 3–26. https://doi.org/10.1016/S0169-409X(00)00129-0
   PubMed Web of Science ®Google Scholar
• Masood, A.M., Ali, H.H., Naeem, M., Latif, M., Bukhari, A.H. and Tanveer, A. (2015). Cyperus rotundus L.: Traditional uses, phytochemistry, and pharmacological activities. Journal of ethnopharmacology, 174, 540–560. https://doi.org/10.1016/j.jep.2015.08.012
   PubMed Web of Science ®Google Scholar
• Meillon-Garcia, L. A., & Demichelis-Gómez, R. (2020). Access to therapy for acute myeloid leukemia in the developing world: Barriers and solutions. Current Oncology Reports, 22(12), 125. https://doi.org/10.1007/s11912-020-00987-8
   PubMed Web of Science ®Google Scholar
• Miller, C. M., O'Sullivan, E. C., & McCarthy, F. O. (2019). Novel 11-substituted ellipticines as potent anticancer agents with divergent activity against cancer cells. Pharmaceuticals (Basel), 12(2), 90. https://doi.org/10.3390/ph12020090 PMID: 31207878; PMCID: PMC6631919.
   PubMedGoogle Scholar
• Nakao, M., Yokota, S., Iwai, T., Kaneko, H., Horiike, S., Kashima, K., Sonoda, Y., Fujimoto, T., & Misawa, S. (1996). Internal tandem duplication of the flt3 gene found in acute myeloid leukemia. Leukemia, 10(12), 1911–1918.
   PubMed Web of Science ®Google Scholar
• Neidle, S. (2012). Design principles for quadruplex-binding small molecules. In Therapeutic applications of quadruplex nucleic acids (pp. 151–174). US: Academic Press:. https://doi.org/10.1016/b978-0-12-375138-6.00009-1
   Google Scholar
• Nombela-Arrieta, C. G., & Manz, M. (2017). Quantification and three-dimensional microanatomical organization of the bone marrow. Blood Adv, 1 (6), 407–416. https://doi.org/10.1182/bloodadvances.2016003194
   PubMed Web of Science ®Google Scholar
• Papaemmanuil, E., Gerstung, M., Bullinger, L., Gaidzik, V. I., Paschka, P., Roberts, N. D., Potter, N. E., Heuser, M., Thol, F., Bolli, N., Gundem, G., Van Loo, P., Martincorena, I., Ganly, P., Mudie, L., McLaren, S., O'Meara, S., Raine, K., Jones, D. R., … Campbell, P. J. (2016). Genomic classification and prognosis in acute myeloid leukemia. The New England Journal of Medicine, 374(23), 2209–2221. https://doi.org/10.1056/NEJMoa1516192
   PubMed Web of Science ®Google Scholar
• Perl, A. E. (2019). Availability of FLT3 inhibitors: How do we use them? Blood, 134 (9), 741–745. https://doi.org/10.1182/blood.2019876821
   PubMed Web of Science ®Google Scholar
• Pires, D. E., Blundell, T. L., & Ascher, D. B. (2015, May 14). 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 Epub 2015 Apr 22. PMID: 25860834; PMCID: PMC4434528.
   PubMed Web of Science ®Google Scholar
• Prasad, S. K., Pradeep, S., Shimavallu, C., Kollur, S. P., Syed, A., Marraiki, N., Egbuna, C., Gaman, M.-A., Kosakowska, O., Cho, W. C., Patrick-Iwuanyanwu, K. C., Ortega, C. J., Frau, J., Flores-Holguín, N., & Glossman-Mitnik, D. (2020). Evaluation of Annona muricata acetogenins as potential anti-SARS-CoV-2 agents through computational approaches. Frontiers in Chemistry, 8, 624716. https://doi.org/10.3389/fchem.2020.624716
   PubMed Web of Science ®Google Scholar
• Prasanth, D., Murahari, M., Chandramohan, V., Panda, S. P., Atmakuri, L. R., & Guntupalli, C. (2020). In silico identification of potential inhibitors from Cinnamon against main protease and spike glycoprotein of SARS CoV-2. Journal of Biomolecular Structure & Dynamics, 39(13), 4618-4632. . Advance online publication. https://doi.org/10.1080/07391102.2020.1779129
   Google Scholar
• Qasaymeh, R. M., Rotondo, D., Oosthuizen, C. B., Lall, N., & Seidel, V. (2019). Predictive binding affinity of plant-derived natural products towards the protein kinase G enzyme of Mycobacterium tuberculosis (MtPknG). Plants (Basel, Switzerland), 8(11), 477. https://doi.org/10.3390/plants8110477
   PubMedGoogle Scholar
• Schneider, G. (2013). Prediction of drug-like properties. In: Madame Curie Bioscience Database [Internet]. Landes Bioscience. 2000–2013. https://www.ncbi.nlm.nih.gov/books/NBK6404/.
   Google Scholar
• Simmler, C., Pauli, G. F., & Chen, S. N. (2013). Phytochemistry and biological properties of glabridin. Fitoterapia, 90, 160–184. https://doi.org/10.1016/j.fitote.2013.07.003
   PubMed Web of Science ®Google Scholar
• Small, D. (2006). FLT3 mutations: Biology and treatment. Hematology. American Society of Hematology. Education Program, 2006(1), 178–184. https://doi.org/10.1182/asheducation-2006.1.178
   Google Scholar
• Stiborová, M., Bieler, C. A., Wiessler, M., & Frei, E. (2001). The anticancer agent ellipticine on activation by cytochrome P450 forms covalent DNA adducts⋆1. Biochemical Pharmacology, 62(12), 1675–1684. https://doi.org/10.1016/S0006-2952(01)00806-1
   PubMed Web of Science ®Google Scholar
• Sutamtewagul, G., & Vigil, C. E. (2018). Clinical use of FLT3 inhibitors in acute myeloid leukemia. OncoTargets and Therapy, 11, 7041–7052. https://doi.org/10.2147/OTT.S171640
   PubMed Web of Science ®Google Scholar
• Turner, A. M., Lin, N. L., Issarachai, S., Lyman, S. D., & Broudy, V. C. (1996). FLT3 receptor expression on the surface of normal and malignant human hematopoietic cells. Blood, 88(9), 3383–3390. Nov 1PMID: 8896403.
   PubMed Web of Science ®Google Scholar
• Vos, T., Allen, C., Arora, M., Barber, R. M., Bhutta, Z. A., Brown, A., Carter, A., Casey, D. C., Charlson, F. J., Chen, A. Z., Coggeshall, M., Cornaby, L., Dandona, L., Dicker, D. J., Dilegge, T., Erskine, H. E., Ferrari, A. J., Fitzmaurice, C., Fleming, T., … Murray, C. J. L. (2016, October). Global, regional, and national incidence, prevalence, and years lived with disability for 310 diseases and injuries, 1990-2015: A systematic analysis for the Global Burden of Disease Study 2015. The Lancet, 388 (10053), 1545–1602. https://doi.org/10.1016/S0140-6736(16)31678-6
   PubMed Web of Science ®Google Scholar
• Wang, B., Yang, L. P., Zhang, X. Z., Huang, S. Q., Bartlam, M., & Zhou, S. F. (2009). New insights into the structural characteristics and functional relevance of the human cytochrome P450 2D6 enzyme. Drug Metabolism Reviews, 41 (4), 573–643. https://doi.org/10.1080/03602530903118729
   PubMed Web of Science ®Google Scholar
• Wang, H., Naghavi, M., Allen, C., Barber, R. M., Bhutta, Z. A., Carter, A., Casey, D. C., Charlson, F. J., Chen, A. Z., Coates, M. M., Coggeshall, M., Dandona, L., Dicker, D. J., Erskine, H. E., Ferrari, A. J., Fitzmaurice, C., Foreman, K., Forouzanfar, M. H., Fraser, M. S., … Murray, C. J. L. ((2016, October ). Global, regional, and national life expectancy, all-cause mortality, and cause-specific mortality for 249 causes of death, 1980-2015: A systematic analysis for the Global Burden of Disease Study 2015. The Lancet, 388 (10053), 1459–1544. https://doi.org/10.1016/S0140-6736(16)31012-1
   PubMed Web of Science ®Google Scholar
• Wang, S., Su, R., Nie, S., Sun, M., Zhang, J., Wu, D., & Moustaid-Moussa, N. (2014). Application of nanotechnology in improving bioavailability and bioactivity of diet-derived phytochemicals. The Journal of Nutritional Biochemistry, 25(4), 363–376. https://doi.org/10.1016/j.jnutbio.2013.10.002
   PubMed Web of Science ®Google Scholar
• Willian, E. A d L., Pereira, A. F., Castro, A. A. d., Cunha, E. F. F d., & Ramalho, T. C. (2016). Flexibility in the molecular design of acetylcholinesterase reactivators: probing representative conformations by chemometric techniques and docking/QM calculations. Letters in Drug Design & Discovery, 13(5), 360–371. https://doi.org/10.2174/1570180812666150918191550
   Web of Science ®Google Scholar
• Zanger, U. M., & Schwab, M. (2013, April). Cytochrome P450 enzymes in drug metabolism: Regulation of gene expression, enzyme activities, and impact of genetic variation. Pharmacology & Therapeutics, 138 (1), 103–141. https://doi.org/10.1016/j.pharmthera.2012.12.007 PMID 23333322.
   PubMed Web of Science ®Google Scholar
• Zhang, K., Liu, Z., Yao, Y., Qiu, Y., Li, F., Chen, D., Hamilton, D. J., Li, Z., & Jiang, S. (2021). Structure-based design of a selective class I histone deacetylase (HDAC) near-infrared (NIR) probe for epigenetic regulation detection in Triple-Negative Breast Cancer (TNBC). Journal of Medicinal Chemistry, 64 (7), 4020–4033. https://doi.org/10.1021/acs.jmedchem.0c02161
   PubMed Web of Science ®Google Scholar
• Zhong, X., Zhu, Y., Lu, Q., Zhang, J., Ge, Z., & Zheng, S. (2006). Silymarin causes caspases activation and apoptosis in K562 leukemia cells through inactivation of Akt pathway. Toxicology, 227(3), 211–216. https://doi.org/10.1016/j.tox.2006.07.021
   PubMed Web of Science ®Google Scholar