Vitamin D3 derivatives with adamantane or lactone ring side chains are cell type-selective vitamin D receptor modulators

Molecular Pharmacology

Volumn 71, Issue 5, 2007, Pages 1298-1311

  Inaba, Yuka ^a,b   Yamamoto, Keiko ^a   Yoshimoto, Nobuko ^a   Matsunawa, Manabu ^b   Uno, Shigeyuki ^b   Yamada, Sachiko ^a,b   Makishima, Makoto ^b  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^b NIHON UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE; CALCITRIOL; COLECALCIFEROL; LACTONE; PROTEIN P160; RETINOID X RECEPTOR; STEROID RECEPTOR COACTIVATOR 1; VITAMIN D RECEPTOR; CADHERIN; CALCITRIOL RECEPTOR; CYTOCHROME P450; DRUG DERIVATIVE; NUCLEAR RECEPTOR COACTIVATOR 2; REPRESSOR PROTEIN; STEROID MONOOXYGENASE; THYROID HORMONE ASSOCIATED PROTEIN COMPLEX; TRANSCRIPTION FACTOR; UNCLASSIFIED DRUG; VITAMIN D 24 HYDROXYLASE; VITAMIN D 24-HYDROXYLASE;

ARTICLE; BIOLOGICAL ACTIVITY; CALCIUM HOMEOSTASIS; CELL DIFFERENTIATION; GENE EXPRESSION; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; LIGAND BINDING; PRIORITY JOURNAL; CELL LINE; CELL STRAIN HCT116; CHEMICAL STRUCTURE; CHEMISTRY; COENZYME; DIMERIZATION; DRUG ANTAGONISM; DRUG EFFECT; GENE EXPRESSION REGULATION; GENETICS; METABOLISM; PROTEIN TERTIARY STRUCTURE;

ADAMANTANE; CADHERINS; CELL LINE; CHOLECALCIFEROL; COENZYMES; CYTOCHROME P-450 ENZYME SYSTEM; DIMERIZATION; GENE EXPRESSION REGULATION; HCT116 CELLS; HUMANS; LACTONES; MODELS, MOLECULAR; NUCLEAR RECEPTOR COACTIVATOR 2; PROTEIN STRUCTURE, TERTIARY; RECEPTORS, CALCITRIOL; REPRESSOR PROTEINS; RETINOID X RECEPTORS; STEROID HYDROXYLASES; TRANSCRIPTION FACTORS;

EID: 34247525093     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.106.032318     Document Type: Article

References (42)

1. Adachi R, Honma Y, Masuno H, Kawana K, Shimomura I, Yamada S, and Makishima M (2005) Selective activation of vitamin D receptor by lithocholic acid acetate, a bile acid derivative. J Lipid Res 46:46-57.
2. Adachi R, Shulman AI, Yamamoto K, Shimomura I, Yamada S, Mangelsdorf DJ, and Makishima M (2004) Structural determinants for vitamin D receptor response to endocrine and xenobiotic signals. Mol Endocrinol 18:43-52.
3. Bledsoe RK, Madauss KP, Holt JA, Apolito CJ, Lambert MH, Pearce KH, Stanley TB, Stewart EL, Trump RP, Willson TM, et al. (2005) A ligand-mediated hydrogen bond network required for the activation of the mineralocorticoid receptor. J Biol Chem 280:31283-31293.
4. Bouillon R, Van Cromphaut S, and Carmeliet G (2003) Intestinal calcium absorption: molecular vitamin D mediated mechanisms. J Cell Biochem 88:332-339.
5. Brzozowski AM, Pike ACW, Dauter Z, Hubbard RE, Bonn T, Engstrom O, Ohman L, Greene GL, Gustafsson J-A, and Carlquist M (1997) Molecular basis of agonism and antagonism in the oestrogen receptor. Nature (Lond) 389:753-758.
6. Castillo AI, Sanchez-Martinez R, Jimenez-Lara AM, Steinmeyer A, Zugel U, and Aranda A (2006) Characterization of vitamin D receptor ligands with cell-specific and dissociated activity. Mol Endocrinol 20:3093-3104.
7. Chen W, Chen G, Head DL, Mangelsdorf DJ, and Russell DW (2007) Enzymatic reduction of oxysterols impairs LXR signaling in cultured cells and the livers of mice. Cell Metab 5:73-79.
8. DeLuca HF (2004) Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr 80:1689S-1696.
9. Geller DS, Farhi A, Pinkerton N, Fradley M, Moritz M, Spitzer A, Meinke G, Tsai FTF, Sigler PB, and Lifton RP (2000) Activating mineralocorticoid receptor mutation in hypertension exacerbated by pregnancy. Science (Wash DC) 289:119-123.
10. Haussler MR, Whitfield GK, Haussler CA, Hsieh JC, Thompson PD, Selznick SH, Dominguez CE, and Jurutka PW (1998) The nuclear vitamin D receptor: biological and molecular regulatory properties revealed. J Bone Miner Res 13:325-349.
11. 3 is mediated by a lack of ligand-induced vitamin D receptor interaction with coactivators. J Biol Chem 275:16506-16512.
12. 3 show cell-specific actions. Chem Biol 7:885-894.
13. 3 from pagetic bone marrow cells. J Steroid Biochem Mol Biol 89-90:331-334.
14. Kaneko E, Matsuda M, Yamada Y, Tachibana Y, Shimomura I, and Makishima M (2003) Induction of intestinal ATP-binding cassette transporters by a phytosterol-derived liver X receptor agonist. J Biol Chem 278:36091-36098.
15. Kim S, Shevde NK, and Pike JW (2005) 1,25-Dihydroxyvitamin D3 stimulates cyclic vitamin D receptor/retinoid X receptor DNA-binding, co-activator recruitment, and histone acetylation in intact osteoblasts. J Bone Miner Res 20:305-317.
16. Kitagawa H, Fujiki R, Yoshimura K, Mezaki Y, Uematsu Y, Matsui D, Ogawa S, Unno K, Okubo M, Tokita A, et al. (2003) The chromatin-remodeling complex WINAC targets a nuclear receptor to promoters and is impaired in Williams syndrome. Cell 113:905-917.
17. Ma Y, Khalifa B, Yee YK, Lu J, Memezawa A, Savkur RS, Yamamoto Y, Chintalacharuvu SR, Yamaoka K, Stayrook KR, et al. (2006) Identification and characterization of noncalcemic, tissue-selective, nonsecosteroidal vitamin D receptor modulators. J Clin Investig 116:892-904.
18. Makishima M (2005) Nuclear receptors as targets for drug development: regulation of cholesterol and bile acid metabolism by nuclear receptors. J Pharmacol Sci 97:177-183.
19. Makishima M, Lu TT, Xie W, Whitfield GK, Domoto H, Evans RM, Haussler MR, and Mangelsdorf DJ (2002) Vitamin D receptor as an intestinal bile acid sensor. Science (Wash DC) 296:1313-1316.
20. Makishima M and Yamada S (2005) Targeting the vitamin D receptor: advances in drug discovery. Expert Opin Ther Pat 15:1133-1145.
21. Malik S and Roeder RG (2005) Dynamic regulation of pol II transcription by the mammalian Mediator complex. Trends Biochem Sci 30:256-263.
22. Michigami T, Suga A, Yamazaki M, Shimizu C, Cai G, Okada S, and Ozono K (1999) Identification of amino acid sequence in the hinge region of human vitamin D receptor that transfers a cytosolic protein to the nucleus. J Biol Chem 274:33531-33538.
23. Miyauchi Y, Michigami T, Sakaguchi N, Sekimoto T, Yoneda Y, Pike JW, Yamagata M, and Ozono K (2005) Importin 4 is responsible for ligand-independent nuclear translocation of vitamin D receptor. J Biol Chem 280:40901-40908.
24. Morita K, Kawana K, Sodeyama M, Shimomura I, Kagechika H, and Makishima M (2005) Selective allosteric ligand activation of the retinoid X receptor heterodimers of NGFI-B and Nurr1. Biochem Pharmacol 71:98-107.
25. Nagpal S, Na S, and Rathnachalam R (2005) Noncalcemic actions of vitamin D receptor ligands. Endocr Rev 26:662-687.
26. Nakano H, Matsunawa M, Yasui A, Adachi R, Kawana K, Shimomura I, and Makishima M (2005) Enhancement of ligand-dependent Vitamin D receptor transactivation by the cardiotonic steroid bufalin. Biochem Pharmacol 70:1479-1486.
27. Oda Y, Sihlbom C, Chalkley RJ, Huang L, Rachez C, Chang C-PB, Burlingame AL, Freedman LP, and Bikle DD (2003) Two distinct coactivators, DRIP/Mediator and SRC/p160, are differentially involved in vitamin D receptor transactivation during keratinocyte differentiation. Mol Endocrinol 17:2329-2339.
28. 3 analogue toward vitamin D receptor function. J Biol Chem 274:32376-32381.
29. Pascussi JM, Robert A, Nguyen M, Walrant-Debray O, Garabedian M, Martin P, Pineau T, Saric J, Navarro F, Maurel P, et al. (2005) Possible involvement of pregnane X receptor-enhanced CYP24 expression in drug-induced osteomalacia. J Clin Investig 115:177-186.
30. Pissios P, Tzameli I, Kushner P, and Moore DD (2000) Dynamic stabilization of nuclear receptor ligand binding domains by hormone or corepressor binding. Mol Cell 6:245-253.
31. Rochel N, Wurtz JM, Mitschler A, Klaholz B, and Moras D (2000) The crystal structure of the nuclear receptor for vitamin D bound to its natural ligand. Mol Cell 5:173-179.
32. Rosenfeld MG, Lunyak VV, and Glass CK (2006) Sensors and signals: a coactivator/corepressor/epigenetic code for integrating signal-dependent programs of transcriptional response. Genes Dev 20:1405-1428.
33. Schreiber E, Matthias P, Muller MM, and Schaffner W (1989) Rapid detection of octamer binding proteins with 'mini-extracts', prepared from a small number of cells. Nucleic Acids Res 17:6419.
34. Shiau AK, Barstad D, Loria PM, Cheng L, Kushner PJ, Agard DA, and Greene GL (1998) The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell 95:927-937.
35. Shulman AI, Larson C, Mangelsdorf DJ, and Ranganathan R (2004) Structural determinants of allosteric ligand activation in RXR heterodimers. Cell 116:417-429.
36. Uno S, Dalton TP, Dragin N, Curran CP, Derkenne S, Miller ML, Shertzer HG, Gonzalez FJ, and Nebert DW (2006) Oral benzo[a]pyrene in Cyp1 knockout mouse lines: CYP1A1 important in detoxication, CYP1B1 metabolism required for immune damage independent of total-body burden and clearance rate. Mol Pharmacol 69:1103-1114.
37. 3. J Mol Biol 350:65-77.
38. Vaisanen S, Perakyla M, Karkkainen JI, Steinmeyer A, and Carlberg C (2002) Critical role of helix 12 of the vitamin D(3) receptor for the partial agonism of carboxylic ester antagonists. J Mol Biol 315:229-238.
39. Van Cromphaut SJ, Dewerchin M, Hoenderop JGJ, Stockmans I, Van Herck E, Kato S, Bindels RJM, Collen D, Carmeliet P, Bouillon R, et al. (2001) Duodenal calcium absorption in vitamin D receptor-knockout mice: Functional and molecular aspects. Proc Natl Acad Sci USA 98:13324-13329.
40. Yamada S, Shimizu M, and Yamamoto K (2003) Structure-function relationships of vitamin D including ligand recognition by the vitamin D receptor. Med Res Rev 23:89-115.
41. 3 and its 20-epimer: compounds for study of the three-dimensional structure of vitamin D responsible for binding to the receptor. J Med Chem 39:2727-2737.
42. Yamamoto K, Abe D, Yoshimoto N, Choi M, Yamagishi K, Tokiwa H, Shimizu M, Makishima M, and Yamada S (2006) Vitamin D receptor: ligand recognition and allosteric network. J Med Chem 49:1313-1324.