Structural evaluation of the agonistic action of a vitamin D analog with two side chains binding to the nuclear vitamin D receptor

Molecular Pharmacology

Volumn 63, Issue 6, 2003, Pages 1230-1237

  Väisänen, Sami ^a   Peräkylä, Mikael ^a   Kärkkäinen, Jouni I ^a   Uskokovic, Milan R ^b   Carlberg, Carsten ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b BioXell   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALCITRIOL; CELL NUCLEUS RECEPTOR; GEMINI; LIGAND; RO 272310; RO 4383582; RO 4383586; UNCLASSIFIED DRUG; VITAMIN D DERIVATIVE; VITAMIN D RECEPTOR;

ARTICLE; BINDING AFFINITY; COMPLEX FORMATION; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG POTENTIATION; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR DYNAMICS; MUTANT; PRIORITY JOURNAL; PROTEIN FAMILY; SIMULATION;

ANIMALS; CALCITRIOL; COMPUTER SIMULATION; HUMANS; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; RABBITS; RECEPTORS, CALCITRIOL; RECEPTORS, CYTOPLASMIC AND NUCLEAR; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSFECTION; TUMOR CELLS, CULTURED; VITAMIN D;

EID: 0038779277     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: 10.1124/mol.63.6.1230     Document Type: Article

References (32)

1. Beato M, Herrlich P, and Schütz G (1995) Steroid hormone receptors: many actors in search of a plot. Cell 83:851-857.
2. Bouillon R, Okamura WH, and Norman AW (1995) Structure-function relationships in the vitamin D endocrine system. Endocr Rev 16:200-257.
3. Bourguet W, Germain P, and Gronemeyer H (2000) Nuclear receptor ligand-binding domains: three-dimensional structures, molecular interactions and pharmacological implications. Trends Pharmacol Sci 21:381-388.
4. 3 analogues with two side chains. J Cell Biochem 81:179-190.
5. 3 receptor agonists designed for topical treatment of skin diseases. J Invest Dermatol 116:785-792.
6. 3. Interplay with retinoid and thyroid hormone signalling. Eur J Biochem 231:517-527.
7. Carlberg C, Bendik I, Wyss A, Meier E, Sturzenbecker LJ, Grippo JF, and Hunziker W (1993) Two nuclear signalling pathways for vitamin D. Nature (Lond) 361:657-660.
8. 3. Crit Rev Eukaryot Gene Expr 8:19-42.
9. 3 analogues. Steroids 66:213-221.
10. Chawla A, Repa JJ, Evans RM, and Mangelsdorf DJ (2001) Nuclear receptors and lipid physiology: opening the X-files. Science (Wash DC) 294:1866-1870.
11. Cornell WD, Cieplak P, Bayly CI, Gould I, Merz KM, Ferguson D, Spellmeyer DC, Fox T, Caldwell JW, and Kollman PA (1995) A second generation force field for the simulation of proteins, nucleic acids and organic molecules. J Am Chem Soc 117:5179-5197.
12. DeLuca HF, Krisinger J, and Darwish H (1990) The vitamin D system. Kidney Int 38:S2-S8.
13. Feng W, Ribeiro RCJ, Wagner RL, Nguyen H, Apriletti JA, Fletterick RJ, Baxter JD, Kushner PJ, and West BL (1998) Hormone-dependent coactivator binding to a hydrophobic cleft on nuclear receptors. Science (Wash DC) 280:1747-1749.
14. Freedman LP (1999) Increasing the complexity of coactivation in nuclear receptor signaling. Cell 97:5-8.
15. 3 receptor permits sensitive interaction with agonists. Mol Pharmacol 57:1206-1217.
16. 3 receptor by interaction with co-repressors and co-activators. J Mol Biol 304:793-801.
17. 3 receptor binding site found in the rat atrial natriuretic factor promoter. Biochem Biophys Res Commun 218:882-886.
18. Levin AA, Sturzenbecker LJ, Kazmer S, Bosakowski T, Huselton C, Allenby G, Speck J, Kratzeisen C, Rosenberger M, Lovey A, et al. (1992) 9-cis-Retinoic acid stereoisomer binds and activates the nuclear receptor RXRα. Nature (Lond) 355:359-361.
19. 3 analogs with BIS C-20 side chains. U.S. Patent 6,008,209. 1999 Dec 28.
20. 3 analogs with BIS C-20 side chains. U.S. Patent 6,030,962. 2000 Feb 29.
21. Mangelsdorf DJ, Thummel C, Beato M, Herrlich P, Schütz G, Umesono K, Blumberg B, Kastner P, Mark M, Chambon P, et al. (1995) The nuclear receptor superfamily: the second decade. Cell 83:835-839.
22. 3 with two side chains: interaction with its nuclear receptor and cellular actions. J Med Chem 43:2719-2730.
23. Rochel N, Wurtz JM, Mitschler A, Klaholz B, and Moras D (2000) Crystal structure of the nuclear receptor for vitamin D bound to its natural ligand. Mol Cell 5:173-179.
24. Simmerling CL and Elber R (1995) Computer determination of peptide conformations in water: different roads to structure. Proc Natl Acad Sci USA 92:3190-3193.
25. Tocchini-Valentini G, Rochel N, Wurtz JM, Mitschler A, and Moras D (2001) Crystal structures of the vitamin D receptor complexed to superagonist 20-epi ligands. Proc Natl Acad Sci USA 98:5491-5496.
26. 3 analog with two side-chains, in Vitamin D: Chemistry, Biology and Clinical Applications of the Steroid Hormone. Proceedings of the 10th International Vitamin D Workshop; 1997 May 24; Strasbourg, France (Norman AW, Bouillon R, Thomasset M, eds) pp. 19-21, University of California, Riverside, CA.
27. 3 receptor for the partial agonism of carboxylic ester antagonists. J Mol Biol 315:229-238.
28. Väisänen S, Ryhänen S, Saarela JT, Peräkyla M, Andersin T, and Maenpää PH (2002b) Structurally and functionally important amino acids of the agonistic conformation of the human vitamin D receptor. Mol Pharmacol 62:788-794.
29. 3 analog KH1060. Proc Natl Acad Sci USA 93:10685-10690.
30. Voegel JJ, Heine MJS, Zechel C, Chambon P, and Gronemeyer H (1996) TIF2, a 160 kDa transcriptional mediator for the ligand-dependent activation function AF-2 of nuclear receptors. EMBO (Eur Mol Biol Organ) J 15:3667-3675.
31. Walters MR (1992) Newly identified actions of the vitamin D endocrine system. Endocr Rev 13:719-764.
32. Wurtz J-M, Bourguet W, Renaud J-P, Vivat V, Chambon P, Moras D, and Gronemeyer H (1996) A canonical structure for the ligand-binding domain of nuclear receptors. Nat Struct Biol 3:87-94.