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Research Articles

Molecular docking and CoMFA studies of thiazoloquin(az)olin(on)es as CD38 inhibitors: determination of inhibitory mechanism, pharmacophore interactions, and design of new inhibitors

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Pages 1890-1898 | Received 27 Mar 2016, Accepted 31 May 2016, Published online: 26 Sep 2016

References

  • Aalizadeh, R., Pourbasheer, E., & Ganjali, M. R. (2015). Analysis of B-RafV600E inhibitors using 2D and 3D-QSAR, molecular docking and pharmacophore studies. Molecular Diversity, 19, 915–930. doi:10.1007/s11030-015-9626-y
  • Andersson, M. (2009). A comparison of nine PLS1 algorithms. Journal of Chemometrics, 23, 518–529. doi:10.1002/cem.1248
  • Baroni, M., Costantino, G., Cruciani, G., Riganelli, D., Valigi, R., & Clementi, S. (1993). Generating optimal linear PLS estimations (GOLPE): An advanced chemometric tool for handling 3D-QSAR problems. Quantitative Structure Activity Relationships, 12, 9–20. doi:10.1002/qsar.19930120103
  • Chini, E. N. (2009). CD38 as a regulator of cellular NAD: A novel potential pharmacological target for metabolic conditions. Current Pharmaceutical Design, 15, 57–63. doi:10.2174/138161209787185788
  • Chiou, S.-Y., Weng, T.-T., Lin, G.-Z., Lu, R.-J., Jian, S.-Y., & Lin, G. (2015). Molecular docking of different inhibitors and activators to butyrylcholinesterase. Journal of Biomolecular Structure & Dynamics, 33, 563–572. doi:10.1080/07391102.2014.896749
  • Deaglio, S., Mehta, K., & Malavasi, F. (2001). Human CD38: A (r)evolutionary story of enzymes and receptors. Leukemia Research, 25, 1–12. doi:10.1016/S0145-2126(00)00093-X
  • Dong, M., Si, Y.-Q., Sun, S.-Y., Pu, X.-P., Yang, Z.-J., Zhang, L.-R., … Lee, H. C. (2011). Design, synthesis and biological characterization of novel inhibitors of CD38. Organic & Biomolecular Chemistry, 9, 3246–3257. doi:10.1039/c0ob00768d
  • Haffner, C. D., Becherer, J. D., Boros, E. E., Cadilla, R., Carpenter, T., Cowan, D., … Ulrich, J. C. (2015). Discovery, synthesis, and biological evaluation of thiazoloquin(az)olin(on)es as potent CD38 inhibitors. Journal of Medicinal Chemistry, 58, 3548–3571. doi:10.1021/jm502009h
  • Hsu, K.-C., Chen, Y.-F., Lin, S.-R., & Yang, J.-M. (2011). iGEMDOCK: A graphical environment of enhancing GEMDOCK using pharmacological interactions and post-screening analysis. BMC Bioinformatics, 12(Suppl 1), S33. doi:10.1186/1471-2105-12-S1-S33
  • HyperChem Release 7.1 for windows molecular modeling system program package, HyperCube. (2002).
  • Kang, C.-M., Liu, D.-Q., Zhao, X.-H., Dai, Y.-J., Cheng, J.-G., & Lv, Y.-T. (2016). QSAR and molecular docking studies on oxindole derivatives as VEGFR-2 tyrosine kinase inhibitors. Journal of Receptors and Signal Transduction, 36, 103–109. doi:10.3109/10799893.2015.1049364
  • Kastenholz, M. A., Pastor, M., Cruciani, G., Haaksma, E. E. J., & Fox, T. (2000). GRID/CPCA: A new computational tool to design selective ligands. Journal of Medicinal Chemistry, 43, 3033–3044. doi:10.1021/jm000934y
  • Kellenberger, E., Kuhn, I., Schuber, F., & Muller-Steffner, H. (2011). Flavonoids as inhibitors of human CD38. Bioorganic & Medicinal Chemistry Letters, 21, 3939–3942. doi:10.1016/j.bmcl.2011.05.022
  • Liu, Q., Kriksunov, I. A., Graeff, R., Munshi, C., Lee, H. C., & Hao, Q. (2006). Structural basis for the mechanistic understanding of human CD38-controlled multiple catalysis. Journal of Biological Chemistry, 281, 32861–32869. doi:10.1074/jbc.M606365200
  • Liu, Q., Kriksunov, I. A., Jiang, H., Graeff, R., Lin, H., Lee, H. C., & Hao, Q. (2008). Covalent and noncovalent intermediates of an NAD utilizing enzyme, human CD38. Chemistry & Biology, 15, 1068–1078. doi:10.1016/j.chembiol.2008.08.007
  • Macalino, S. J. Y., Gosu, V., Hong, S., & Choi, S. (2015). Role of computer-aided drug design in modern drug discovery. Archives of Pharmacal Research, 38, 1686–1701. doi:10.1007/s12272-015-0640-5
  • Maganti, L., Consortium, O., & Ghoshal, N. (2015). 3D-QSAR studies and shape based virtual screening for identification of novel hits to inhibit MbtA in Mycobacterium tuberculosis. Journal of Biomolecular Structure & Dynamics, 33, 344–364. doi:10.1080/07391102.2013.872052
  • McCarthy, T. V., Datar, S., & Mackrill, J. J. (2003). Activation of ryanodine receptor/Ca2+ release channels downregulates CD38 in the Namalwa B lymphoma. FEBS Letters, 554, 133–137. doi:10.1016/S0014-5793(03)01122-0
  • Moreau, C., Liu, Q., Graeff, R., Wagner, G. K., Thomas, M. P., Swarbrick, J. M., … Potter, B. V. L. (2013). CD38 structure-based inhibitor design using the N1-cyclic inosine 59-diphosphate ribose template. PLoS ONE, 8, e66247. doi:10.1371/journal.pone.0066247
  • Pastor, M., Cruciani, G., & Clementi, S. (1997). Smart region definition: A new way to improve the predictive ability and interpretability of three-dimensional quantitative structure-activity relationships. Journal of Medicinal Chemistry, 40, 1455–1464. doi:10.1021/jm9608016
  • Richmond, N. J., Willett, P., & Clark, R. D. (2004). Alignment of three-dimensional molecules using an image recognition algorithm. Journal of Molecular Graphics & Modelling, 23, 199–209. doi:10.1016/j.jmgm.2004.04.004
  • Salmina, A. B., Lopatina, O., Ekimova, M. V., Mikhutkina, S. V., & Higashida, H. (2010). CD38/cyclic ADP-ribose system: A new player for oxytocin secretion and regulation of social behaviour. Journal of Neuroendocrinology, 22, 380–392. doi:10.1111/j.1365-2826.2010.01970.x
  • Shibi, I. G., Aswathy, L., Jisha, R. S., Masand, V. H., Divyachandran, A., & Gajbhiye, J. M. (2015). Molecular docking and QSAR analyses for understanding the antimalarial activity of some 7-substituted-4-aminoquinoline derivatives. European Journal of Pharmaceutical Sciences, 77, 9–23. doi:10.1016/j.ejps.2015.05.025
  • Sun, L., Iqbal, J., Zaidi, S., Zhu, L.-L., Zhang, X., Peng, Y., … Zaidi, M. (2006). Structure and functional regulation of the CD38 promoter. Biochemical and Biophysical Research Communications, 341, 804–809. doi:10.1016/j.bbrc.2006.01.033
  • Swarbrick, J. M., Graeff, R., Zhang, H., Thomas, M. P., Hao, Q., & Potter, B. V. L. (2014). Cyclic adenosine 5′-diphosphate ribose analogs without a “Southern” ribose inhibit ADP-ribosyl cyclase-hydrolase CD38. Journal of Medicinal Chemistry, 57, 8517–8529. doi:10.1021/jm501037u
  • Tosco, P., & Balle, T. (2011). Open3DQSAR: A new open-source software aimed at high-throughput chemometric analysis of molecular interaction fields. Journal of Molecular Modeling, 17, 201–208. doi:10.1007/s00894-010-0684-x
  • Tosco, P., Balle, T., & Shiri, F. (2011). Open3DALIGN: An open-source software aimed at unsupervised ligand alignment. Journal of Computer-Aided Molecular Design, 25, 777–783. doi:10.1007/s10822-011-9462-9
  • Wang, F., Yang, W., Shi, Y., & Le, G. (2015). 3D-QSAR, molecular docking and molecular dynamics studies of a series of RORγt inhibitors. Journal of Biomolecular Structure & Dynamics, 33, 1929–1940. doi:10.1080/07391102.2014.980321
  • Wang, S., Zhu, W., Wang, X., Li, J., Zhang, K., Zhang, L., … Zhang, L. (2014). Design, synthesis and SAR studies of NAD analogues as potent inhibitors towards CD38 NADase. Molecules, 19, 5754–15767. doi:10.3390/molecules191015754
  • Wu, D., Ting, K., Duan, Y., Li, N., Li, J., Zhang, L., … Zhang, L. (2013). Synthesis and activity of novel indole derivatives as inhibitors of CD38. Acta Pharmaceutica Sinica B, 3, 245–253. doi:10.1016/j.apsb.2013.05.003
  • Yang, J.-M. (2004). Development and evaluation of a generic evolutionary method for protein – ligand docking. Journal of Computational Chemistry, 25, 843–857. doi:10.1002/jcc.20013
  • Yang, J.-M., & Chen, C.-C. (2004). GEMDOCK: A generic evolutionary method for molecular docking. Proteins, 55, 288–304. doi:10.1002/prot.20035
  • Yang, J.-M., & Shen, T.-W. (2005). A pharmacophore-based evolutionary approach for screening selective estrogen receptor modulators. Proteins, 59, 205–220. doi:10.1002/prot.20387
  • Yuriev, E., & Ramsland, P. A. (2013). Latest developments in molecular docking: 2010–2011 in review. Journal of Molecular Recognition, 26, 215–239. doi:10.1002/jmr.2266
  • Zhang, S., Xue, X., Zhang, L., Zhang, L., & Liu, Z. (2015). Comparative analysis of pharmacophore features and quantitative structure-activity relationships for CD38 covalent and non-covalent inhibitors. Chemical Biology & Drug Design, 86, 1411–1424. doi:10.1111/cbdd.12606
  • Zhou, Y., Ting, K. Y., Lam, C. M. C., Kwong, A. K. Y., Xia, J., Jin, H., … Zhang, L. (2012). Design, synthesis and biological evaluation of noncovalent inhibitors of human CD38 NADase. ChemMedChem, 7, 223–228. doi:10.1002/cmdc.201100487

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