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Research Article

An integrated molecular modeling approach for in silico design of new tetracyclic derivatives as ALK inhibitors

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Pages 488-504 | Received 23 Sep 2015, Accepted 07 Dec 2015, Published online: 12 Jan 2016

References

  • Hubbard SR, Till JH. Protein tyrosine kinase structure and function. Annu Rev Biochem 2000;69:373–98
  • Morris SW, Naeve C, Mathew P, et al. ALK, the Chromosome 2 gene locus altered by the t (2; 5) in non-Hodgkin’s lymphoma, encodes a novel neural receptor tyrosine kinase that is highly related to leukocyte tyrosine kinase (LTK). Oncogene 1997;14:2175–88
  • Pulford K, Lamant L, Morris SW, et al. Detection of anaplastic lymphoma kinase (ALK) and nucleolar protein nucleophosmin (NPM)-ALK proteins in normal and neoplastic cells with the monoclonal antibody ALK1. Blood 1997;89:1394–404
  • Shiota M, Fujimoto J, Semba T, et al. Hyperphosphorylation of a novel 80 kDa protein-tyrosine kinase similar to Ltk in a human Ki-1 lymphoma cell line, AMS3. Oncogene 1994;9:1567–74
  • Morris SW, Kirstein MN, Valentine MB, et al. Fusion of a kinase gene, ALK, to a nucleolar protein gene, NPM, in non-Hodgkin’s lymphoma. Science 1994;263:1281–4
  • Li R, Morris SW. Development of anaplastic lymphoma kinase (ALK) small-molecule inhibitors for cancer therapy. Med Res Rev 2008;28:372–412
  • Mano H. Non-solid oncogenes in solid tumors: EML4-ALK fusion genes in lung cancer. Cancer Sci 2008;99:2349–55
  • Koivunen JP, Mermel C, Zejnullahu K, et al. EML4-ALK fusion gene and efficacy of an ALK kinase inhibitor in lung cancer. Clin Cancer Res 2008;14:4275–83
  • Osajima Hakomori Y, Miyake I, Ohira M, et al. Biological role of anaplastic lymphoma kinase in neuroblastoma. Am J Pathol 2005;167:213–22
  • Mosse YP, Laudenslager M, Longo L, et al. Identification of ALK as a major familial neuroblastoma predisposition gene. Nature 2008;455:930–5
  • Roskoski R Jr, Anaplastic lymphoma kinase (ALK): structure, oncogenic activation, and pharmacological inhibition. Pharmacol Res 2013;68:68–94
  • Cui JJ, Tran-Dube 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;54:6342–63
  • Kinoshita K, Ono Y, Emura T, et al. Discovery of novel tetracyclic compounds as anaplastic lymphoma kinase inhibitors. Bioorg Med Chem Lett 2011;21:3788–93
  • Kinoshita K, Asoh K, Furuichi N, et al. Design and synthesis of a highly selective, orally active and potent anaplastic lymphoma kinase inhibitor (CH5424802). Bioorg Med Chem 2012;20:1271–80
  • Kinoshita K, Kobayashi T, Asoh K, et al. 9Substituted 6,6 Dimethyl-11-oxo-6,11-dihydro-5H-benzo[b] carbazoles as highly selective and potent anaplastic lymphoma kinase inhibitors. J Med Chem 2011;54:6286–94
  • Markus AL. Multi-dimensional QSAR in drug discovery. Drug Discov Today 2007;12:1013–17
  • Sakamoto H, Tsukaguchi T, Hiroshima S, et al. CH5424802, a selective ALK inhibitor capable of blocking the resistant gatekeeper mutant. Cancer Cell 2011;19:679–90
  • Friesner RA, Banks JL, Murphy RB, et al. Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J Med Chem 2004;47:1739–49
  • Gasteiger J, Marsili M. Iterative partial equalization of orbital electro negativity – a rapid access to atomic charges. Tetrahedron 1980;36:3219–28
  • Cramer RD, Patterson DE, Bunce JD. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 1988;110:5959–67
  • Klebe G, Abraham U, Mietzner T. Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J Med Chem 1994;37:4130–46
  • Wold S, Johansson A. Cochi M. PLS-Partial least squares projection to latent structures. In: Kubinyl H, ed. 3D-QSAR in drug design: theory, methods and application. Leiden: Science; 1993:523–50
  • Cramer RD, Bunce JD, Patterson DE, Frank IE. Crossvalidation, bootstrapping, and partial least squares compared with multiple regression in conventional QSAR studies. Quant Struct Act Relat 1988;7:18–25
  • Wold S. Cross-validatory estimation of the number of components in factor and principal components models. Technometrics 1978;20:397–405
  • Halgren TA. Identifying and characterizing binding sites and assessing druggability. J Chem Inf Model 2009;49:377–89
  • D. E. Shaw Research. Desmond 3.8. New York (NY): D. E. Shaw Research; 2014
  • Kaminski GA, Friesner RA. Evaluation and reparametrization of the OPLS-AA force field for proteins via comparison with accurate quantum chemical calculations on peptides. J Phys Chem 2001;105:6474–87
  • Berendsen HJC, Grigera JR, Straatsma TP. The missing term in effective pair potentials. J Phys Chem 1987;91:6269–71
  • Strahan GD, Keniry MA, Shafer RH. NMR structure refinement and dynamics of the K+-[d(G3T4G3)]2 quadruplex via particle mesh Ewald molecular dynamics simulations. Biophys J 1998;75:968–81
  • Andersen HC. Rattle: a velocity version of the shake algorithm for molecular dynamics calculations. J Comput Phys 1983;52:24–34

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