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Research Article

Molecular docking, 3D-QSAR, molecular dynamics, synthesis and anticancer activity of tyrosine kinase 2 (TYK 2) inhibitors

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Pages 462-474 | Received 05 Oct 2018, Accepted 22 Jan 2019, Published online: 30 Apr 2019

References

  • Yoshiya T, Shigeru I, Kunihiro Y. Jak and Syk: emerging their relevance to the treatment of inflammatory diseases. Inflamm Regen. 2011;31:237–244.
  • O'Shea JJ, Pesu M, Borie DC. A new modality for immunosuppression: targeting the JAK/STAT pathway . Nat Rev Drug Discov. 2004;3:555–564.
  • Malemud CJ, Pearlman E. Targeting JAK/STAT signaling pathway in inflammatory diseases. Curr Signal Transduction Ther. 2009;4:201–221.
  • Ghoreschi K, Laurence A, O'Shea JJ. Selectivity and therapeutic inhibition of kinases: to be or not to be? Nat Immunol. 2009;10:356–360.
  • Kisseleva T, Bhattacharya S, Braunstein J. Signaling through the JAK/STAT pathway, recent advances and future challenges. Gene. 2002;285:1–24.
  • Igaz P, Tóth S, Falus A. Biological and clinical significance of the JAK-STAT pathway; lessons from knockout mice. Inflamm Res. 2001;50:435–441.
  • Leonard WJ, O'Shea JJ. JAKS AND STATS: biological implications. Annu Rev Immunol. 1998;16:293–322.
  • Christian S, David EL, Thomas D. JAK-STAT signaling: from interferons to cytokines. J Biol Chem. 2007:282:20059–263.
  • Levy DE, Darnell JE. Jr. Stats: transcriptional control and biological impact. Nat Rev Mol Cell Biol. 2002;3:651–662.
  • Stump KL, Lu LD, Dobrzanski P, et al. A highly selective, orally active inhibitor of Janus kinase 2, CEP-33779, ablates disease in two mouse models of rheumatoid arthritis. Arthritis Res Ther. 2011;13:R68
  • Quint_as-Cardama A, Hagop K, Jorge C, et al. Janus kinase inhibitors for the treatment of myeloproliferative neoplasias and beyond. Nat Rev Drug Discov. 2011;10:127–140.
  • R_obert K, Peter PS, Gy€orgy MK. Recent developments on JAK2 inhibitors: a patent review. Expert Opin Ther Pat. 2010;20:471–495.
  • Domanska D, Brzezianska E. The JAK/STAT protein activation – role in cancer development and targeted therapy. CST. 2012;7:187–201.
  • Caflisch A, Ehrhardt C. Structure-based combinatorial ligand design, in: P. Veerapandian (Ed). Structure-based drug design. New York (NY): Marcel Dekker; 1997. p. 541–558.
  • Cho SJ, Garsia MLS, Bier J, et al. Structure- based alignment and comparative molecular field analysis of acetylcholinesterase inhibitors. J Med Chem. 1996;39:5064–5071.
  • Sippl W, Contreras JM, Parrot I, et al. Structure-based 3D QSAR and design of novel acetylcholinesterase inhibitors. J. Comput. Aided. Mol. Des. 2001;15:395–410.
  • Sippl W Receptor-based 3D QSAR analysis of estrogen receptor ligands merging the accuracy of receptor-based alignments with the computational efficiency of ligand-based methods. J. Comput. Aided Mol Des. 2000;14:559–572.
  • Cramer RD, 3rd, 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;110:5959–5967.
  • Cramer RD, Bunce JD, Patterson DE, et al. Cross validation, bootstrapping, and partial least squares compared with multiple regression in conventional QSAR studies. Quant Struct-Act Relat. 1988;7:18–25.
  • 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;37:4130–4146.
  • Liang J, van Abbema A, Balazs M, et al. Lead optimization of a 4-aminopyridine benzamide scaffold to identify potent, selective, and orally bioavailable TYK2 inhibitors. J Med Chem. 2013;56:4521–4536.
  • Schrodinger LLC. New York Glide Version 5.6; 2010.
  • 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;47:1739–1749.
  • Liang J, Vickie T, Anne Van A, et al. Lead identification of novel and selective TYK2 inhibitors. Eur J Med Chem. 2013;67:175–187. 2013;
  • Sybyl-X 2.1. St. Louis (MO): Tripos Associates; 2012.
  • Gasteiger J, Marsili M. Iterative partial equalization of orbital electro negativity a rapid access to atomic charges. Tetrahedron 1980;36:3219–3228. (80)80168-2.
  • Ramesh I, Srilata B, Sree Kanth S, et al. Molecular docking, 3D QSAR and dynamics simulation studies of imidazo-pyrrolopyridines as janus kinase 1 (JAK 1) inhibitors. Comp Bio Chem. 2016;64:33–46.
  • Shaw DE. 2014. Research, DESMOND (Version 3.8), New York.
  • Kaminski GA, Friesner RA, Tirado-Rives J, et al. Evaluation and reparametrization of the OPLS-AA force field for proteins via comparison with accurate quantum chemical calculations on peptides. J Phys Chem B. 2001;105:6474–6487.
  • Berendsen HJC, Grigera JR, Straatsma TP. The missing term in effective pair potentials. J Phys Chem. 1987;91:6269–6271.
  • Srilata B, Ramesh I, Sree Kanth S, et al. Structural insights of Staphylococcus aureus FtsZ inhibitors through molecular docking, 3D-QSAR and molecular dynamics simulations. J Recept Signal Transduc. 2018;38:61–70.
  • Ramesh I, Srilata B, Sree Kanth S, et al. Molecular modeling-driven approach for identification of Janus kinase 1 inhibitors through 3D-QSAR, docking and molecular dynamics simulations. J Recept Signal Transduc. 2017;37:453–469.
  • Sree Kanth S, Vijjulatha M. Molecular docking and 3D-QSAR studies on triazolinone and pyridazinone, non-nucleoside inhibitor of HIV-1 reverse transcriptase. J Mol Mod. 2010;16:1169–1178.
  • Kadir OY, Edip T. Synthesis, docking and biological evaluation of oxamide and fumaramide analogs as potential AChE and BuChE inhibitors. Med Chem Res. 2015;24:588–602. DOI 10.1007/s00044-014-1152-4.
  • Falcó JL, Piqué M, González M, et al. Synthesis, pharmacology and molecular modeling of N-substituted 2-phenyl-indoles and benzimidazoles as potent GABAA agonists. Eur J Med Chem. 2006;41:8985–8990.

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