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Identification of an N-oxide pyridine GW4064 analog as a potent FXR agonist.

Feng S, Yang M, Zhang Z, Wang Z, Hong D, Richter H, Benson GM, Bleicher K, Grether U, Martin RE, Plancher JM, Kuhn B, Rudolph MG, Chen L
Bioorg Med Chem Lett 19 2595-8 (2009)
Cited: 29 times
EuropePMC logo PMID: 19328688

Abstract

According to the docking studies and the analysis of a co-crystal structure of GW4064 with FXR, a series of 3-aryl heterocyclic isoxazole analogs were designed and synthesized. N-Oxide pyridine analog (7b) was identified as a promising FXR agonist with potent binding affinity and good efficacy, supporting our hypothesis that through an additional hydrogen bond interaction between the pyridine substituent of isoxazole analogs and Tyr373 and Ser336 of FXR, binding affinity and functional activity could be improved.

Articles - 3fxv mentioned but not cited (6)

  1. Pharmacophore-based discovery of FXR agonists. Part I: Model development and experimental validation. Schuster D, Markt P, Grienke U, Mihaly-Bison J, Binder M, Noha SM, Rollinger JM, Stuppner H, Bochkov VN, Wolber G. Bioorg Med Chem 19 7168-7180 (2011)
  2. Side-Chain Conformational Preferences Govern Protein-Protein Interactions. Watkins AM, Bonneau R, Arora PS. J Am Chem Soc 138 10386-10389 (2016)
  3. Impact of domain knowledge on blinded predictions of binding energies by alchemical free energy calculations. Mey ASJS, Jiménez JJ, Michel J. J Comput Aided Mol Des 32 199-210 (2018)
  4. Binding free energy predictions of farnesoid X receptor (FXR) agonists using a linear interaction energy (LIE) approach with reliability estimation: application to the D3R Grand Challenge 2. Rifai EA, van Dijk M, Vermeulen NPE, Geerke DP. J Comput Aided Mol Des 32 239-249 (2018)
  5. Identified the Synergistic Mechanism of Drynariae Rhizoma for Treating Fracture Based on Network Pharmacology. Lin H, Wang X, Wang L, Dong H, Huang P, Cai Q, Mo Y, Huang F, Jiang Z. Evid Based Complement Alternat Med 2019 7342635 (2019)
  6. Discovery of Novel Molecular Frameworks of Farnesoid X Receptor Modulators by Ensemble Machine Learning. Merk D, Grisoni F, Schaller K, Friedrich L, Schneider G. ChemistryOpen 8 7-14 (2019)


Reviews citing this publication (5)

  1. FXR signaling in the enterohepatic system. Matsubara T, Li F, Gonzalez FJ. Mol Cell Endocrinol 368 17-29 (2013)
  2. Role of farnesoid X receptor in cholestasis. Yuan ZQ, Li KW. J Dig Dis 17 501-509 (2016)
  3. Farnesoid X receptor modulators: a patent review. Crawley ML. Expert Opin Ther Pat 20 1047-1057 (2010)
  4. Bile-ology: from bench to bedside. Jin LH, Fang ZP, Fan MJ, Huang WD. J Zhejiang Univ Sci B 20 414-427 (2019)
  5. Characterizing ligands for farnesoid X receptor--available in vitro test systems for farnesoid X receptor modulator development. Merk D, Steinhilber D, Schubert-Zsilavecz M. Expert Opin Drug Discov 9 27-37 (2014)

Articles citing this publication (18)

  1. D3R Grand Challenge 2: blind prediction of protein-ligand poses, affinity rankings, and relative binding free energies. Gaieb Z, Liu S, Gathiaka S, Chiu M, Yang H, Shao C, Feher VA, Walters WP, Kuhn B, Rudolph MG, Burley SK, Gilson MK, Amaro RE. J Comput Aided Mol Des 32 1-20 (2018)
  2. Pharmacophore-based discovery of FXR-agonists. Part II: identification of bioactive triterpenes from Ganoderma lucidum. Grienke U, Mihály-Bison J, Schuster D, Afonyushkin T, Binder M, Guan SH, Cheng CR, Wolber G, Stuppner H, Guo DA, Bochkov VN, Rollinger JM. Bioorg Med Chem 19 6779-6791 (2011)
  3. Extending SAR of bile acids as FXR ligands: discovery of 23-N-(carbocinnamyloxy)-3α,7α-dihydroxy-6α-ethyl-24-nor-5β-cholan-23-amine. Gioiello A, Macchiarulo A, Carotti A, Filipponi P, Costantino G, Rizzo G, Adorini L, Pellicciari R. Bioorg Med Chem 19 2650-2658 (2011)
  4. NSAIDs Ibuprofen, Indometacin, and Diclofenac do not interact with Farnesoid X Receptor. Schmidt J, Klingler FM, Proschak E, Steinhilber D, Schubert-Zsilavecz M, Merk D. Sci Rep 5 14782 (2015)
  5. Combining self- and cross-docking as benchmark tools: the performance of DockBench in the D3R Grand Challenge 2. Salmaso V, Sturlese M, Cuzzolin A, Moro S. J Comput Aided Mol Des 32 251-264 (2018)
  6. Using physics-based pose predictions and free energy perturbation calculations to predict binding poses and relative binding affinities for FXR ligands in the D3R Grand Challenge 2. Athanasiou C, Vasilakaki S, Dellis D, Cournia Z. J Comput Aided Mol Des 32 21-44 (2018)
  7. Asymmetric synthesis of the four diastereoisomers of a novel non-steroidal farnesoid X receptor (FXR) agonist: role of the chirality on the biological activity. Marinozzi M, Carotti A, Sardella R, Buonerba F, Ianni F, Natalini B, Passeri D, Rizzo G, Pellicciari R. Bioorg Med Chem 21 3780-3789 (2013)
  8. Pyrazole[3,4-e][1,4]thiazepin-7-one derivatives as a novel class of Farnesoid X Receptor (FXR) agonists. Marinozzi M, Carotti A, Sansone E, Macchiarulo A, Rosatelli E, Sardella R, Natalini B, Rizzo G, Adorini L, Passeri D, De Franco F, Pruzanski M, Pellicciari R. Bioorg Med Chem 20 3429-3445 (2012)
  9. Simultaneous diastereo- and enantioseparation of farnesoid X receptor (FXR) agonists with a quinine carbamate-based chiral stationary phase. Sardella R, Marinozzi M, Ianni F, Lisanti A, Natalini B. Anal Bioanal Chem 405 847-862 (2013)
  10. Design, Synthesis, and Biological Evaluation of Novel Nonsteroidal Farnesoid X Receptor (FXR) Antagonists: Molecular Basis of FXR Antagonism. Huang H, Si P, Wang L, Xu Y, Xu X, Zhu J, Jiang H, Li W, Chen L, Li J. ChemMedChem 10 1184-1199 (2015)
  11. Discovery and SAR study of hydroxyacetophenone derivatives as potent, non-steroidal farnesoid X receptor (FXR) antagonists. Liu P, Xu X, Chen L, Ma L, Shen X, Hu L. Bioorg Med Chem 22 1596-1607 (2014)
  12. Fragmentation of GW4064 led to a highly potent partial farnesoid X receptor agonist with improved drug-like properties. Flesch D, Gabler M, Lill A, Gomez RC, Steri R, Schneider G, Stark H, Schubert-Zsilavecz M, Merk D. Bioorg Med Chem 23 3490-3498 (2015)
  13. Blinded evaluation of farnesoid X receptor (FXR) ligands binding using molecular docking and free energy calculations. Selwa E, Elisée E, Zavala A, Iorga BI. J Comput Aided Mol Des 32 273-286 (2018)
  14. CDOCKER and λ-dynamics for prospective prediction in D₃R Grand Challenge 2. Ding X, Hayes RL, Vilseck JZ, Charles MK, Brooks CL. J Comput Aided Mol Des 32 89-102 (2018)
  15. Workflows and performances in the ranking prediction of 2016 D3R Grand Challenge 2: lessons learned from a collaborative effort. Gao YD, Hu Y, Crespo A, Wang D, Armacost KA, Fells JI, Fradera X, Wang H, Wang H, Sherborne B, Verras A, Peng Z. J Comput Aided Mol Des 32 129-142 (2018)
  16. Modern drug design: the implication of using artificial neuronal networks and multiple molecular dynamic simulations. Yakovenko O, Jones SJM. J Comput Aided Mol Des 32 299-311 (2018)
  17. Performance of multiple docking and refinement methods in the pose prediction D3R prospective Grand Challenge 2016. Fradera X, Verras A, Hu Y, Wang D, Wang H, Fells JI, Armacost KA, Crespo A, Sherborne B, Wang H, Peng Z, Gao YD. J Comput Aided Mol Des 32 113-127 (2018)
  18. Selective Optimization of Pranlukast to Farnesoid X Receptor Modulators. Schierle S, Schmidt J, Kaiser A, Merk D. ChemMedChem 13 2530-2545 (2018)


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