Journal of Integrative Natural Science (통합자연과학논문집)

The Basic Science Institute Chosun University (조선대학교 기초과학연구원)
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Comparative Molecular Similarity Indices Analysis (CoMSIA) of 8-substituted-2-aryl-5-alkylaminoquinolines as Corticotropin-releasing factor-1 Receptor Antagonists

  • Received : 2016.10.17
  • Accepted : 2016.12.25
  • Published : 2016.12.31
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Abstract

Corticotropin-releasing factor receptors (CRFRs) activate the hypothalamic-pituitary-adrenal axis, which is an integral part of the fight or flight response to stress. Increase in CRH level is observed in Alzheimer's disease and major depression and hypoglycemia. Here, we report on the relevant physicochemical parameters required for the CRFR inhibitors. Comparative molecular similarity indices analysis (CoMSIA) was performed with the derivatives of 8-substituted-2-aryl-5-alkylaminoquinolinesas CRFR inhibitors. The best predictions were obtained for the best CoMSIA model with a $q^2$ of 0.576 with 6 components and $r^2$ of 0.977. The statistical parameters from the generated CoMSIA models indicated that the data are well fitted and have high predictive ability. CoMSIA contour maps could be useful in the designing of more potent and novel CRFR derivatives.

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References

  1. B. P. Grone and K. P. Maruska, "A second corticotropin-releasing hormone gene (CRH2) is conserved across vertebrate classes and expressed in the hindbrain of a basal neopterygian fish, the spotted gar", J. Comp. Neurol., Vol. 523, pp. 1125-1143, 2015. https://doi.org/10.1002/cne.23729
  2. R. L. Hauger, D. E. Grigoriadis, M. F. Dallman, P. M. Plotsky, W. W. Vale, and F. M. Dautzenberg, "International union of pharmacology. XXXVI. Current status of the nomenclature for receptors for corticotropin-releasing factor and their ligands" Pharmacol. Rev., Vol. 55, pp. 21-26, 2003. https://doi.org/10.1124/pr.55.1.3
  3. N. Sato, K. Takagi, T. Suzuki, Y. Miki, S. Tanaka, S. Nagase, H. Warita, S. Fukudo, F. Sato, H. Sasano, and K. Ito, "Immunolocalization of corticotropin-releasing hormone (CRH) and its receptors (CRHR1 and CRHR2) in human endometrial carcinoma: CRHR1 as a potent prognostic factor", Int. J. Gynecol. Cancer, Vol. 24, pp. 1549-1557, 2014. https://doi.org/10.1097/IGC.0000000000000269
  4. F. Stamatelou, E. Deligeoroglou, N. Vrachnis, S. Iliodromiti, Z. Iliodromiti, S. Sifakis, G. Farmakides, and G. Creatsas, "Corticotropin-releasing hormone and progesterone plasma levels association with the onset and progression of labor", Clin. Exp. Obstet. Gyn., Vol. 40, pp. 568-571, 2013.
  5. F. C. Raadsheer, J. J. V. Heerikhuize, P. J. Lucassen, W. J. Hoogendijk, F. J. Tilders, and D. F. Swaab, "Corticotropin-releasing hormone mRNA levels in the paraventricular nucleus of patients with Alzheimer's disease and depression", Am. J. Psychiat., Vol. 152, pp. 1372-1376, 1995. https://doi.org/10.1176/ajp.152.9.1372
  6. H.-B. Fan, T. Zhang, K. Sun, S.-P. Song, S.-B. Cao, H.-L. Zhang, and W. Shen, "Corticotropin-releasing factor mediates bone cancer induced pain through neuronal activation in rat spinal cord", Tumor Biol., Vol. 36, pp. 9559-9565, 2015. https://doi.org/10.1007/s13277-015-3670-1
  7. V. Coric, H. H. Feldman, D. A. Oren, A. Shekhar, J. Pultz, R. C. Dockens, X. Wu, K. A. Gentile, S.-P. Huang, E. Emison, T. Delmonte, B. B. D'Souza, D. L. Zimbroff, J. A. Grebb, A. W. Goddard, and E. G. Stock, "Multicenter, randomized, doubleblind, active comparator and placebo-controlled trial of a corticotropin-releasing factor receptor-1 antagonist in generalized anxiety disorder", Depress Anxiety, Vol. 27, pp. 417-425, 2010. https://doi.org/10.1002/da.20695
  8. E. M. Jutkiewicz, S. K. Wood, H. Houshyar, L.-W. Hsin, K. C. Rice, and J. H. Woods, "The effects of CRF antagonists, antalarmin, CP154, 526, LWH234, and R121919, in the forced swim test and on swim-induced increases in adrenocorticotropin in rats", Psychopharmacology, Vol. 180, pp. 215-223, 2005. https://doi.org/10.1007/s00213-005-2164-z
  9. B. Binneman, D. Feltner, S. Kolluri, Y. Shi, R. Qiu, and T. Stiger, "A 6-week randomized, placebo-controlled trial of CP-316,311 (a selective CRH1 antagonist) in the treatment of major depression", Am. J. Psychiat., Vol. 165, pp. 617-620, 2008. https://doi.org/10.1176/appi.ajp.2008.07071199
  10. R. Pastor, C. S. Mckinnon, A. C. Scibelli, S. Burkhart-Kasch, C. Reed, A. E. Ryabinin, S. C. Coste, M. P. Stenzel-Poore, and T. J. Phillips, "Corticotropin-releasing factor-1 receptor involvement in behavioral neuroadaptation to ethanol: A urocortin1-independent mechanism", Proc. Natl. Acad. Sci. U.S.A., Vol. 105, pp. 9070-9075, 2008. https://doi.org/10.1073/pnas.0710181105
  11. K. Takedaa, T. Terauchi, M. Hashizume, K. Shikata, R. Taguchi, K. Murata-Tai, M. Fujisawa, Y. Takahashi, K. Shin, M. Ino, H. Shibata, and M. Yonaga, "Synthesis and structure-activity relationships of 8-substituted-2-aryl-5-alkylaminoquinolines: Potent, orally active corticotropin-releasing factor-1 receptor antagonists", Bioorgan. Med. Chem., Vol. 20, pp. 6559-6578, 2012. https://doi.org/10.1016/j.bmc.2012.09.028
  12. S. J. Cho and A. Tropsha, "Cross-validated R2-guided region selection for comparative molecular field analysis: A simple method to achieve consistent results", J. Med. Chem., Vol. 38, pp. 1060-1066, 1995. https://doi.org/10.1021/jm00007a003
  13. S. Wold, M. Sjostrom, and L. Eriksson, "PLSregression: a basic tool of chemometrics", Chemometr. Intell. Lab., Vol. 58, pp. 109-130, 2001. https://doi.org/10.1016/S0169-7439(01)00155-1
  14. U. Debnath, S. Verma, S. Jain, S. B. Katti, and Y. S. Prabhakar, "Pyridones as NNRTIs against HIV-1 mutants: 3D-QSAR and protein informatics", J. Comput. Aid. Mol. Des., Vol. 27, pp. 637-654, 2013. https://doi.org/10.1007/s10822-013-9667-1
  15. D. Fernandez, J. Ortega-Castro, and J. Frau, "Human farnesyl pyrophosphate synthase inhibition by nitrogen bisphosphonates: A 3D-QSAR study", J. Comput. Aid. Mol. Des., Vol. 27, pp. 739-754, 2013. https://doi.org/10.1007/s10822-013-9674-2
  16. N. Santhosh Kumar and M. Thirumurthy, "3DQSAR studies of 8-substituted-2-aryl-5-alkylaminoquinolines as Corticotropin-releasing factor-1 receptor antagonists." J. Chosun Natural Sci., Vol. 8, pp. 176-183, 2015. https://doi.org/10.13160/ricns.2015.8.3.176

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