Dual potent c-Met and ALK inhibitors: from common feature pharmacophore modeling to structure based virtual screening

References

• Lemmon MA, Schlessinger J. Cell signaling by receptor tyrosine kinases. Cell. 2010;141(7):1117–1134.
   PubMed Web of Science ®Google Scholar
• McDonell LM, Kernohan KD, Boycott KM, et al. Receptor tyrosine kinase mutations in developmental syndromes and cancer: two sides of the same coin. Hum Mol Genet. 2015;24(R1):R60–R66.
   PubMedGoogle Scholar
• Cui JJ, Tran-Dubé M, Shen H, et al. Structure based drug design of crizotinib (PF-02341066), a potent and selective dual inhibitor of mesenchymal–epithelial transition factor (c-MET) kinase and anaplastic lymphoma kinase (ALK). J Med Chem. 2011;54(18):6342–6363.
   PubMed Web of Science ®Google Scholar
• Salgia R. MET in lung cancer: biomarker selection based on scientific rationale. Mol Cancer Ther. 2017;16(4):555–565.
   PubMed Web of Science ®Google Scholar
• Fu Y-T, Zheng H-B, Zhou L, et al. Valproic acid, targets papillary thyroid cancer through inhibition of c-Met signalling pathway. Am J Translat Res. 2017;9(6):3138–3147.
   PubMed Web of Science ®Google Scholar
• Liu X, Newton RC, Scherle PA. Developing c-MET pathway inhibitors for cancer therapy: progress and challenges. Trends Mol Med. 2010;16(1):37–45.
   PubMed Web of Science ®Google Scholar
• Parikh PK, Ghate MD. Recent advances in the discovery of small molecule c-Met kinase inhibitors. Eur J Med Chem. 2018;143:1103–1138.
   PubMed Web of Science ®Google Scholar
• Bahrami A, Shahidsales S, Khazaei M, et al. C‐Met as a potential target for the treatment of gastrointestinal cancer: Current status and future perspectives. J Cell Physiol. 2017;232(10):2657–2673.
   PubMed Web of Science ®Google Scholar
• Caenepeel S, Cooke K, Wadsworth S, et al. MAPK pathway inhibition induces MET and GAB1 levels, priming BRAF mutant melanoma for rescue by hepatocyte growth factor. Oncotarget. 2017;8(11):17795.
   PubMedGoogle Scholar
• Kitamura Y, Hirotab S. Oncogenic protein tyrosine kinases. Cmls, Cell Mol Life Sci. 2004;61(23):2924–2931.
   PubMed Web of Science ®Google Scholar
• Perez-Pinera P, Chang Y, Astudillo A, et al. Anaplastic lymphoma kinase is expressed in different subtypes of human breast cancer. Biochem Biophys Res Commun. 2007;358(2):399–403.
   PubMed Web of Science ®Google Scholar
• Mossé YP, Laudenslager M, Longo L, et al. Identification of ALK as a major familial neuroblastoma predisposition gene. Nature. 2008;455(7215):930–935.
   PubMed Web of Science ®Google Scholar
• Carén H, Abel F, Kogner P, et al. High incidence of DNA mutations and gene amplifications of the ALK gene in advanced sporadic neuroblastoma tumours. Biochem J. 2008;416(2):153–159.
   PubMedGoogle Scholar
• Murugan AK, Xing M. Anaplastic thyroid cancers harbor novel oncogenic mutations of the ALK gene. Cancer Res. 2011;71:4403–4411.
   PubMed Web of Science ®Google Scholar
• Iams WT, Lovly CM. Anaplastic Lymphoma Kinase (ALK) as a therapeutic target in non-small cell lung cancer. Cancer J (Sudbury, Mass). 2015;21(5):378–382.
   PubMed Web of Science ®Google Scholar
• Ou S-H, Kwak EL, Siwak-Tapp C, et al. Activity of crizotinib (PF02341066), a dual mesenchymal-epithelial transition (MET) and anaplastic lymphoma kinase (ALK) inhibitor, in a non-small cell lung cancer patient with de novo MET amplification. J Thorac Oncol. 2011;6(5):942–946.
   PubMed Web of Science ®Google Scholar
• Abdolmaleki A, Ghasemi J, Shiri F, et al. Application of Multivariate Linear and Nonlinear Calibration and Classification Methods in Drug Design. CCHTS. 2015;18(8):795–808. doi:10.2174/1386207318666150803142158.
   Google Scholar
• Mashayekh K, Sharifi S, Damghani T, et al. Clustering and Sampling of the c-Met Conformational Space: A Computational Drug Discovery Study. Comb Chem High Throughput Screen. 2019;22(9):635–648. doi:10.2174/1386207322666191024103902. 31696808
   PubMed Web of Science ®Google Scholar
• Zhang W, Pei J, Lai L. Computational multitarget drug design. J Chem Inf Model. 2017;57(3):403–412.
   PubMed Web of Science ®Google Scholar
• Pirhadi S, Shiri F, Ghasemi JB. Pharmacophore elucidation and 3D-QSAR analysis of a new class of highly potent inhibitors of acid ceramidase based on maximum common substructure and field fit alignment methods. J Iran Chem Soc. 2014;11(5):1329–1336.
   Web of Science ®Google Scholar
• Meng L, Shu M, Chen Y, et al. A novel lead compound CM-118: Antitumor activity and new insight into the molecular mechanism and combination therapy strategy in c-Met-and ALK-dependent cancers. Cancer Biol Ther. 2014;15(6):721–734.
   PubMed Web of Science ®Google Scholar
• Yu J, Wang J. Development of a modified process for the kilogram-scale synthesis of c-Met/ALK inhibitor HS-10168. Org Process Res Dev. 2017;21(1):133–137.
   Web of Science ®Google Scholar
• Li J, Wu N, Tian Y, et al. Aminopyridyl/pyrazinyl spiro [indoline-3, 4′-piperidine]-2-ones as highly selective and efficacious c-Met/ALK inhibitors. ACS Med Chem Lett. 2013;4(8):806–810.
   PubMed Web of Science ®Google Scholar
• Liu Z, Ai J, Peng X, et al. Novel 2, 4-diarylaminopyrimidine analogues (DAAPalogues) showing potent c-Met/ALK multikinase inhibitory activities. ACS Med Chem Lett. 2014;5(4):304–308.
   PubMed Web of Science ®Google Scholar
• Cui JJ. Targeting receptor tyrosine kinase MET in cancer: small molecule inhibitors and clinical progress. J Med Chem. 2014;57(11):4427–4453.
   PubMed Web of Science ®Google Scholar
• Kocienski P. Synthesis of c-Met/ALK Inhibitor HS-10168. Synfacts. 2017;13(04):0336.
   Google Scholar
• Schneidman-Duhovny D, Dror O, Inbar Y, et al. PharmaGist: a webserver for ligand-based pharmacophore detection. Nucleic Acids Res. 2008;36(Web Server issue):W223–W228.
   PubMed Web of Science ®Google Scholar
• Sunseri J, Koes DR. Pharmit: interactive exploration of chemical space. Nucleic Acids Res. 2016;44(W1):W442–W448.
   PubMed Web of Science ®Google Scholar
• Jones G, Willett P, Glen RC, et al. Development and validation of a genetic algorithm for flexible docking. J Mol Biol. 1997;267(3):727–748.
   PubMed Web of Science ®Google Scholar
• Damghani T, Sedghamiz T, Sharifi S, et al. Critical c-Met-inhibitor interactions resolved from molecular dynamics simulations of different c-Met complexes. J. Mol. Struct. 2020;1203:127456.doi:10.1016/j.molstruc.2019.127456.
   Web of Science ®Google Scholar