214
Views
15
CrossRef citations to date
0
Altmetric
Research Articles

QSAR analysis of nicotinamidic compounds and design of potential Bruton’s tyrosine kinase (Btk) inhibitors

, , , &
Pages 1421-1440 | Received 02 Apr 2015, Accepted 06 Jul 2015, Published online: 11 May 2016

References

  • Akinleye, A., Chen, Y. M., Mukhi, N., Song, Y. P., & Liu, D. L. (2013). Ibrutinib and novel BTK inhibitors in clinical development. Journal of Hematology & Oncology, 6, 1756–8722.
  • Allinger, N. L. (1977). Conformational analysis. 130. MM2. A hydrocarbon force field utilizing V1 and V2 torsional terms. Journal of the American Chemical Society, 99, 8127–8134.10.1021/ja00467a001
  • Berman, H. M., Battistuz, T., Bhat, T. N., Bluhm, W. F., Bourne, P. E., Burkhardt, K., … Zardecki, C. (2002). The Protein Data Bank. Acta Crystallographica Section D-Biological Crystallography, 58, 899–907.10.1107/S0907444902003451
  • Bolen, J. B. (1995). Protein-tyrosine kinases in the initiation of antigen receptor signaling. Current Opinion in Immunology, 7, 306–311.10.1016/0952-7915(95)80103-0
  • Brown, J. R. (2013). Ibrutinib (PCI-32765), the first BTK (Bruton’s tyrosine kinase) inhibitor in clinical trials. Current Hematologic Malignancy Reports, 8, 1–6.10.1007/s11899-012-0147-9
  • da Cunha, E. F. F., Albuquerque, M. G., Antunes, O. A. C., & de Alencastro, R. B. (2005). 4D-QSAR models of HOE/BAY-793 analogues as HIV-1 protease inhihitors. QSAR & Combinatorial Science, 24, 240–253.
  • da Cunha, E. F. F., Mancini, D. T., & Ramalho, T. C. (2012). Molecular modeling of the Toxoplasma gondii adenosine kinase inhibitors. Medicinal Chemistry Research, 21, 590–600.10.1007/s00044-011-9554-z
  • da Cunha, E. F. F., Martins, R. C. A., Albuquerque, M. G., & Alencastro, R. B. (2004). LIV-3D-QSAR model for estrogen receptor ligands. Journal of Molecular Modeling, 10, 297–304.
  • da Cunha, E. F. F., Resende, J. E., Franca, T. C. C., Gonçalves, M. A., de Souza, F. R., Santos-Garcia, L., & Ramalho, T. C. (2013). Molecular modeling studies of piperidine derivatives as new acetylcholinesterase inhibitors against neurodegenerative diseases. Journal of Chemistry, 2013, 1–7.10.1155/2013/278742
  • Delucca, G. V., Shi, Q., Liu, C., Duan, J., & Tebben, A. J. (2010). New substituted nicotinamide compounds are Bruton’s tyrosine kinase inhibitors, useful for the treatment or prophylaxis of e.g. ulcerative colitis, asthma, Graves’ disease, rheumatoid arthritis, psoriasis, osteoarthritis and osteoporosis. U.S. Patent No. S2012082702. Washington, DC: U.S. Patent and Trademark Office.
  • Di Paolo, J. A., Huang, T., Balazs, M., Barbosa, J., Barck, K. H., Bravo, B. J., … Currie, K. S. (2011). Specific Btk inhibition suppresses B cell- and myeloid cell-mediated arthritis. Nature Chemical Biology, 7, 41–50.10.1038/nchembio.481
  • Emelie, K., Blomberg, M., Smith, C. I. E., & Lindvall, J. M. (2007). Gene expression signatures in primary immunodeficiencies: The experience from human disease and mouse models. Current Molecular Medicine, 7, 555–566.
  • Hantschel, O., Rix, U., Schmidt, U., Burckstummer, T., Kneidinger, M., Schutze, G., …Superti-Furga, G. (2007). The Btk tyrosine kinase is a major target of the Bcr-Abl inhibitor dasatinib. Proceedings of the National Academy of Sciences of the United States of America, 104, 13283–13288.10.1073/pnas.0702654104
  • Honigberg, L. A., Smith, A. M., Sirisawad, M., Verner, E., Loury, D., Chang, B., …Buggy, J. J. (2010). The Bruton tyrosine kinase inhibitor PCI-32765 blocks B-cell activation and is efficacious in models of autoimmune disease and B-cell malignancy. Proceedings of the National Academy of Sciences of the United States of America, 107, 13075–13080.10.1073/pnas.1004594107
  • Hopfinger, A. J., Wang, S., Tokarski, J. S., Jin, B. Q., Albuquerque, M., Madhav, P. J., & Duraiswami, C. (1997). Construction of 3D-QSAR models using the 4D-QSAR analysis formalism. Journal of the American Chemical Society, 119, 10509–10524.10.1021/ja9718937
  • Hyvonen, M., & Saraste, M. (1997). Structure of the PH domain and Btk motif from Bruton’s tyrosine kinase: Molecular explanations for X-linked agammaglobulinaemia. The EMBO Journal, 16, 3396–3404.10.1093/emboj/16.12.3396
  • Janda, E., Palmieri, C., Pisano, A., Pontoriero, M., Iaccino, E., Falcone, C., … Scala, G. (2011). Btk regulation in human and mouse B cells via protein kinase C phosphorylation of IBtkγ. Blood, 117, 6520–6531.10.1182/blood-2010-09-308080
  • Kiralj, R., & Ferreira, M. M. C. (2009). Basic validation procedures for regression models in QSAR and QSPR studies: Theory and application. Journal of the Brazilian Chemical Society, 20, 770–787.10.1590/S0103-50532009000400021
  • Kurosaki, T. (1997). Molecular mechanisms in B cell antigen receptor signaling. Current Opinion in Immunology, 9, 309–318.10.1016/S0952-7915(97)80075-1
  • Lou, Y., Owens, T. D., Kuglstatter, A., Kondru, R. K., & Goldstein, D. M. (2012). Bruton’s tyrosine kinase inhibitors: Approaches to potent and selective inhibition, preclinical and clinical evaluation for inflammatory diseases and B cell malignancies. Journal of Medicinal Chemistry, 55, 4539–4550.10.1021/jm300035p
  • Marcotte, D. J., Liu, Y. T., Arduini, R. M., Hession, C. A., Miatkowski, K., Wildes, C. P., … Silvian, L. F. (2010). Structures of human Bruton’s tyrosine kinase in active and inactive conformations suggest a mechanism of activation for TEC family kinases. Protein Science, 19, 429–439.
  • Mohamed, A. J., Yu, L., Bäckesjö, C. M., Vargas, L., Faryal, R., Aints, A., … Edvard Smith, C. I. (2009). Bruton’s tyrosine kinase (Btk): Function, regulation, and transformation with special emphasis on the PH domain. Immunological Reviews, 228, 58–73.10.1111/imr.2009.228.issue-1
  • Muri, E. M. F., Gomes, M., Costa, J. S., Alencar, F. L., Sales, A., Bastos, M. L., … Antunes, O. A. C. (2004). N-t-Boc-amino acid esters of isomannide – Potential inhibitors of serine proteases. Amino Acids, 27, 153–159.10.1007/s00726-004-0121-5
  • Oliveira, A. A., Ramalho, T. C., & da Cunha, E. F. F. (2009). QSAR study of androstenedione analogs as aromatase inhibitors. Letters in Drug Design & Discovery, 6, 554–562.
  • Pan, Z., Scheerens, H., Li, S.-J., Schultz, B. E., Sprengeler, P. A., Burrill, L. C., … Palmer, J. T. (2007). Discovery of selective irreversible inhibitors for Bruton’s tyrosine kinase. ChemMedChem, 2, 58–61.10.1002/(ISSN)1860-7187
  • Pan, D. H., Tseng, Y. F., & Hopfinger, A. J. (2003). Quantitative structure-based design: Formalism and application of receptor-dependent RD-4D-QSAR analysis to a set of glucose analogue inhibitors of glycogen phosphorylase. Journal of Chemical Information and Modeling, 43, 1591–1607.10.1021/ci0340714
  • Ponader, S., Chen, S. S., Buggy, J. J., Balakrishnan, K., Gandhi, V., Wierda, W. G., … Burger, J. A. (2012). The Bruton tyrosine kinase inhibitor PCI-32765 thwarts chronic lymphocytic leukemia cell survival and tissue homing in vitro and in vivo. Blood, 119, 1182–1189.10.1182/blood-2011-10-386417
  • Scharenberg, A. M., & Kinet, J. P. (1998). Ptdlns-3,4,5-P3: A regulatory nexus between tyrosine kinases and sustained calcium signals. Cell, 94, 5–8.10.1016/S0092-8674(00)81214-3
  • Silva, D. G., Freitas, M. P., da Cunha, E. F. F., Ramalho, T. C., & Nunes, C. A. (2012). Rational design of small modified peptides as ACE inhibitors. MedChemComm, 3, 1290–1293.10.1039/c2md20214j
  • Thangapandian, S., John, S., Sakkiah, S., & Lee, K. W. (2010). Ligand and structure based pharmacophore modeling to facilitate novel histone deacetylase 8 inhibitor design. European Journal of Medicinal Chemistry, 45, 4409–4417.10.1016/j.ejmech.2010.06.024
  • Thomas, J. D., Sideras, P., Smith, C. I. E., Vorechovsky, I., Chapman, V., & Paul, W. E. (1993). Colocalization of X-linked agammaglobulinemia and X-linked immunodeficiency genes. Science, 261, 355–358.10.1126/science.8332900
  • Tsukada, S., Rawlings, D. J., & Witte, O. N. (1994). Role of Bruton’s tyrosine kinase in immunodeficiency. Current Opinion in Immunology, 6, 623–630.10.1016/0952-7915(94)90151-1
  • Tsukada, S., Saffran, D. C., Rawlings, D. J., Parolini, O., Allen, R. C., Klisak, I., … Witte, O. N. (1993). Deficient expression of a B cell cytoplasmic tyrosine kinase in human X-linked agammaglobulinemia. Cell, 72, 279–290.10.1016/0092-8674(93)90667-F
  • Vargas, L., Hamasy, A., Nore, B. F., & Smith, C. I. E. (2013). Inhibitors of BTK and ITK: state of the new drugs for cancer, autoimmunity and inflammatory diseases. Scandinavian Journal of Immunology, 78, 130–139.10.1111/sji.2013.78.issue-2
  • Vetrie, D., Vořechovský, I., Sideras, P., Holland, J., Davies, A., Flinter, F., … Bentley, D. R. (1993). The gene involved in X-linked agammaglobulinaemia is a member of the src family of protein-tyrosine kinases. Nature, 361, 226–233.10.1038/361226a0
  • Vihinen, M., Nilsson, L., & Smith, C. I. E. (1994). Tec homology (TH) adjacent to the PH domain. FEBS Letters, 350, 263–265.10.1016/0014-5793(94)00783-7

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.