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X-ray crystal structure of the novel enhanced-affinity glucocorticoid agonist fluticasone furoate in the glucocorticoid receptor-ligand binding domain.

Biggadike K, Bledsoe RK, Hassell AM, Kirk BE, McLay IM, Shewchuk LM, Stewart EL
J Med Chem 51 3349-52 (2008)
Cited: 55 times
EuropePMC logo PMID: 18522385

Abstract

An X-ray crystal structure is reported for the novel enhanced-affinity glucocorticoid agonist fluticasone furoate (FF) in the ligand binding domain of the glucocorticoid receptor. Comparison of this structure with those of dexamethasone and fluticasone propionate shows the 17 alpha furoate ester to occupy more fully the lipophilic 17 alpha pocket on the receptor, which may account for the enhanced glucocorticoid receptor binding of FF.

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  1. The Biologist's Guide to the Glucocorticoid Receptor's Structure. Deploey N, Van Moortel L, Rogatsky I, Peelman F, De Bosscher K. Cells 12 1636 (2023)

Articles - 3cld mentioned but not cited (4)

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  4. The multivalency of the glucocorticoid receptor ligand-binding domain explains its manifold physiological activities. Jiménez-Panizo A, Alegre-Martí A, Tettey TT, Fettweis G, Abella M, Antón R, Johnson TA, Kim S, Schiltz RL, Núñez-Barrios I, Font-Díaz J, Caelles C, Valledor AF, Pérez P, Rojas AM, Fernández-Recio J, Presman DM, Hager GL, Fuentes-Prior P, Estébanez-Perpiñá E. Nucleic Acids Res 50 13063-13082 (2022)


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  8. Design and x-ray crystal structures of high-potency nonsteroidal glucocorticoid agonists exploiting a novel binding site on the receptor. Biggadike K, Bledsoe RK, Coe DM, Cooper TW, House D, Iannone MA, Macdonald SJ, Madauss KP, McLay IM, Shipley TJ, Taylor SJ, Tran TB, Uings IJ, Weller V, Williams SP. Proc Natl Acad Sci U S A 106 18114-18119 (2009)
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  13. Inhaled fluticasone furoate/vilanterol does not affect hypothalamic-pituitary-adrenal axis function in adolescent and adult asthma: randomised, double-blind, placebo-controlled study. Allen A, Schenkenberger I, Trivedi R, Cole J, Hicks W, Gul N, Jacques L. Clin Respir J 7 397-406 (2013)
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  15. An analysis of glucocorticoid receptor-mediated gene expression in BEAS-2B human airway epithelial cells identifies distinct, ligand-directed, transcription profiles with implications for asthma therapeutics. Joshi T, Johnson M, Newton R, Giembycz M. Br J Pharmacol 172 1360-1378 (2015)
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  17. Discovery of GW870086: a potent anti-inflammatory steroid with a unique pharmacological profile. Uings IJ, Needham D, Matthews J, Haase M, Austin R, Angell D, Leavens K, Holt J, Biggadike K, Farrow SN. Br J Pharmacol 169 1389-1403 (2013)
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  24. Aryl aminopyrazole benzamides as oral non-steroidal selective glucocorticoid receptor agonists. Barnett HA, Coe DM, Cooper TW, Jack TI, Jones HT, Macdonald SJ, McLay IM, Rayner N, Sasse RZ, Shipley TJ, Skone PA, Somers GI, Taylor S, Uings IJ, Woolven JM, Weingarten GG. Bioorg Med Chem Lett 19 158-162 (2009)
  25. Letter Fluticasone furoate/fluticasone propionate - different drugs with different properties. Biggadike K. Clin Respir J 5 183-184 (2011)
  26. Combining 3D-QSAR, docking, molecular dynamics and MM/PBSA methods to predict binding modes for nonsteroidal selective modulator to glucocorticoid receptor. Xu Y, Zhang T, Chen M. Bioorg Med Chem Lett 19 393-396 (2009)
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  28. Investigation on critical structural motifs of ligands for triggering glucocorticoid receptor nuclear migration through molecular docking simulations. Liu YL, Jang S, Wang SM, Chen CH, Li FY. J Biomol Struct Dyn 34 1214-1231 (2016)
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  30. Crystalline forms of 2,2,2-trifluoro-N-[(1R,2S)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-(3-methoxyphenyl)-2-propanyl]acetamide (AZD-5423). Norman P. Expert Opin Ther Pat 23 1239-1245 (2013)
  31. Discovery of indazole ethers as novel, potent, non-steroidal glucocorticoid receptor modulators. Hemmerling M, Edman K, Lepistö M, Eriksson A, Ivanova S, Dahmén J, Rehwinkel H, Berger M, Hendrickx R, Dearman M, Jensen TJ, Wissler L, Hansson T. Bioorg Med Chem Lett 26 5741-5748 (2016)
  32. Pharmacology Versus Convenience: A Benefit/Risk Analysis of Regular Maintenance Versus Infrequent or As-Needed Inhaled Corticosteroid Use in Mild Asthma. Daley-Yates P, Aggarwal B, Lulic Z, Fulmali S, Cruz AA, Singh D. Adv Ther 39 706-726 (2022)
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  34. Structure elucidation and spectroscopic analysis of photodegradants of the anti-rhinitis drug fluticasone furoate. Bardsley B, Smith MS, Gibbon BH. Org Biomol Chem 8 1876-1880 (2010)
  35. Quaternary glucocorticoid receptor structure highlights allosteric interdomain communication. Postel S, Wissler L, Johansson CA, Gunnarsson A, Gordon E, Collins B, Castaldo M, Köhler C, Öling D, Johansson P, Fröderberg Roth L, Beinsteiner B, Dainty I, Delaney S, Klaholz BP, Billas IML, Edman K. Nat Struct Mol Biol 30 286-295 (2023)
  36. Conformational Analysis of Acyclic α-Fluoro Sulfur Motifs. Erdeljac N, Mück-Lichtenfeld C, Daniliuc CG, Gilmour R. Chemistry 26 13704-13715 (2020)


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