22S-Butyl-1α,24R-dihydroxyvitamin D3: Recovery of vitamin D receptor agonistic activity

Journal of Steroid Biochemistry and Molecular Biology

Volumn 121, Issue 1-2, 2010, Pages 146-150

  Inaba, Yuka ^a,b   Nakabayashi, Makoto ^b   Itoh, Toshimasa ^a   Yoshimoto, Nobuko ^a   Ikura, Teikichi ^b   Ito, Nobutoshi ^b   Shimizu, Masato ^b   Yamamoto, Keiko ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

^b TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

Author keywords

Antagonist; Coactivator; Hydrophobic interaction; Nuclear receptor; X ray crystallography

Indexed keywords

22 BUTYL 1ALPHA,24 DIHYDROXYVITAMIN D3; 22 BUTYL 25,26,27 TRINOR 1ALPHA,24 DIHYDROXYVITAMIN D3; AMINO ACID; COLECALCIFEROL DERIVATIVE; HISTIDINE DERIVATIVE; LEUCINE; UNCLASSIFIED DRUG; VITAMIN D DERIVATIVE; VITAMIN D RECEPTOR; 22 BUTYL 1,24 DIHYDROXYVITAMIN D3; 22-BUTYL-1,24-DIHYDROXYVITAMIN D3; CALCITRIOL; CALCITRIOL RECEPTOR; DIHYDROXY VITAMIN D3; DIHYDROXY-VITAMIN D3; DRUG DERIVATIVE; LIGAND; PEPTIDE; RETINOID X RECEPTOR; STEROID RECEPTOR COACTIVATOR 1; VITAMIN D;

ARTICLE; COMPLEX FORMATION; CRYSTALLIZATION; DRUG ACTIVITY; DRUG RECEPTOR BINDING; HYDROGEN BOND; HYDROPHOBICITY; LIGAND BINDING; PROTEIN CONFORMATION; PROTEIN DOMAIN; PROTEIN STABILITY; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY; ANIMAL; BIOLOGICAL MODEL; CELL LINE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; DRUG POTENTIATION; HUMAN; METABOLISM; METHODOLOGY; PROTEIN BINDING;

ANIMALS; CALCITRIOL; CELL LINE; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; HUMANS; LIGANDS; MODELS, BIOLOGICAL; MODELS, CHEMICAL; MODELS, MOLECULAR; NUCLEAR RECEPTOR COACTIVATOR 1; PEPTIDES; PROTEIN BINDING; RECEPTORS, CALCITRIOL; RETINOID X RECEPTORS; VITAMIN D;

EID: 77954760559     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2010.02.033     Document Type: Article

References (11)

1. Vitamin D Second Edition 2005, Elsevier Academic Press. D. Feldman, J.W. Pike, F.H. Glorieux (Eds.).
2. 3-26,23-lactone depends on the primary structure of the carboxyl-terminal region of the vitamin D receptor. Mol. Endocrinol. 2005, 19:1147-1157.
3. 3-26, 23-lactam (DLAMs), antagonize bone resorption via suppressing RANKL expression in osteoblasts. Biochem. Biophys. Res. Commun. 2008, 372:434-439.
4. Kittaka A., Saito N., Honzawa S., Takenouchi K., Ishizuka S., Chen T.C., Peleg S., Kato S., Arai M.A. Creative synthesis of novel vitamin D analogs for health and disease. J. Steroid Biochem. Mol. Biol. 2007, 103:269-276.
5. Inaba Y., Yoshimoto N., Sakamaki Y., Nakabayashi M., Ikura T., Tamamura H., Ito N., Shimizu M., Yamamoto K. A new class of vitamin D analogues that induce structural rearrangement of the ligand-binding pocket of the receptor. J. Med. Chem. 2009, 52:1438-1449.
6. Ciesielski F., Rochel N., Moras D. Adaptability of the vitamin D nuclear receptor to the synthetic ligand Gemini: remodelling the LBP with one side chain rotation. J. Steroid Biochem. Mol. Biol. 2007, 103:235-242.
7. 3 and Gemini: purification, crystallization and preliminary X-ray diffraction analysis. J. Steroid Biochem. Mol. Biol. 2004, 89-90:55-59.
8. 3 26,23-lactones: synthesis, biological activities and molecular basis of passive antagonism. Bioorg. Med. Chem. 2008, 16:457-473.
9. Brünger A.T., Adams P.D., Clore G.M., DeLano W.L., Gros P., Grosse-Kunstleve R.W., Jiang J.-S., Kuszewski J., Nilges M., Pannu N.S., Read R.J., Rice L.M., Simonson T., Warren G.L. Crystallography & NMR system: a new software suite for macromo-lecular structure determination. Acta Crystallogr. 1998, D54:905-921.
10. 3 hormone analogues and a LXXLL-containing coactivator peptide. Biochemistry 2004, 43:4101-4110.
11. 3 compounds of super-agonistic activity: syntheses, biological activities and interaction with the receptor. J. Med. Chem. 2007, 50:932-939.