Three-dimensional structure-function relationship of vitamin D: Side chain location and various activities

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 7, 1999, Pages 1041-1046

  Yamamoto, Keiko ^a   Ooizumi, Hiroshi ^e   Umesono, Kazuhiko ^e   Verstuyf, Annemieke ^b   Bouillon, Roger ^b   DeLuca, Hector F ^c   Shinki, Toshimasa ^d   Suda, Tatsuo ^d   Yamada, Sachiko ^a  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^b UNIVERSITY OF LEUVEN   (Belgium)

^c UNIVERSITY OF WISCONSIN MADISON   (United States)

^d SHOWA UNIVERSITY   (Japan)

^e NONE

Author keywords

[No Author keywords available]

Indexed keywords

22 METHYL 1ALPHA,25 DIHYDROXYVITAMIN D3; CALCITRIOL; CALCIUM; UNCLASSIFIED DRUG; VITAMIN D; VITAMIN D RECEPTOR;

ANIMAL CELL; ARTICLE; BREAST CANCER; CALCIUM BONE LEVEL; CALCIUM CELL LEVEL; CALCIUM MOBILIZATION; CALCIUM TRANSPORT; CELL DIFFERENTIATION; CONTROLLED STUDY; DIASTEREOISOMER; DRUG CONFORMATION; DRUG POTENCY; DRUG RECEPTOR BINDING; GENETIC TRANSCRIPTION; HUMAN; HUMAN CELL; KERATINOCYTE; LEUKEMIA CELL; LIGAND BINDING; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; BIOLOGICAL TRANSPORT; BONE AND BONES; CALCITRIOL; CALCIUM; CELL DIFFERENTIATION; CELL DIVISION; HUMANS; INTESTINES; KERATINOCYTES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; RATS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

ANIMALIA;

EID: 0033526059     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00129-8     Document Type: Article

References (26)

1. 1. Feldman, D.; Glorieux, F. H.; Pike, J. W. Eds. (1997). Vitamin D. Academic Press.
2. 2. (a) Jurutka, P. W.; Hsieh, J.-C.; Remus, L. S.; Whitfield, G. K.; Thompson, P. D.; Haussler, C. A.; Blanco, J. C. G.; Ozato, K.; Haussler, M. R. J. Biol. Chem. 1997, 272, 14592-14599.
3. (b) Brzozowski, A. M.; Pike, A. C. W.; Dauter, Z.;Hubbard, R. E.; Bonn, T.; Engström, O.; Öhman, L.; Greene, G. L.; Gustafsson, J.-A.; Carlquist, M. Nature, 1997, 389, 753-758.
4. (c) Feng, W. J.; Ribeiro, R. C. J.; Wagner R. L.; Nguyen, H.; Apriletti, J. W.; Fletterick, R. J.; Baxter, J. D.; Kushner, P. J.; West, B. L. Science, 1998, 280, 1747-1749.
5. 3. (a) Yamamoto, K.; Takahashi, J.; Hamano, K.; Yamada, S.; Yamaguchi, K.; DeLuca, H. F. J. Org. Chem. 1993, 58, 2530-2537.
6. (b) Yamamoto, K.; Ohta, M.; DeLuca, H. F.; Yamada, S. Bioorg. Med. Chem. Lett. 1995, 5, 979-984.
7. (c) Ishida, H.; Shimizu, M.; Yamamoto, K.; Iwasaki, Y.; Yamada, S.; Yamaguchi, K. J. Org. Chem. 1995, 60, 1828-1833.
8. (d) Yamamoto, K.; Sun, W-Y.; Ohta, M.; Hamada, K.; DeLuca, H. F.; Yamada, S. J. Med. Chem. 1996, 39, 2727-2737.
9. 4. Binderup, L.; Latini, S.; Binderup, E.; Bretting, C.; Calverley, M.; Hansen, K. Biochem. Pharm. 1991, 42, 1569-1575.
10. 5. Yamada, S.; Yamamoto, K.; Masuno H.; Ohta, M. J. Med. Chem. 1998, 41, 1467-1475.
11. 6. Bouillon, R.; Okamura, W. H.; Norman, A. W., Endocrine Rev., 1995, 16, 200-257.
12. 7. (a) Transfection was carried out via calcium-phosphate precipitation method. The cells were transfected for 6 hours, and after the DNA precipitates were washed, they were incubated for 36 hours with or without the ligand. Cells were harvested and assayed for luciferase and β-galactosidase activity. All points were duplicated.
13. (b) Umesono, K.; Murakami, K. K.; Thompson, C. C.; Evanas, R. M. Cell 1991, 65, 1255-1266.
14. 8. Forman, B. M.; Umesono, K.; Chen, J.; Evans, R. M. Cell 1995, 81, 541-550.
15. 9. Peleg, S.; Sastry, M.; Collins, E. D.; Bishop, J. E.; Norman, A. W. J. Biol. Chem. 1995, 270, 10551-10558.
16. 10. Ostrem, V. K.; Lau, W. F.; Lee, S. H.; Perlman, K.; Schnoes, H. K.; DeLuca, H. F.; Ikekawa, N. J. Biol. Chem. 1987, 262, 14164-14171.
17. 11. Allewaert, K.; Zhao, X. Y.; Zhao, J.; Glibert, F.; Branisteanu, D.; De Clercq P.; Vandewalle, M.; Bouillon, R. Steroids. 1995, 60, 324-332.
18. 12. (a) Rats were maintained on a 0.47% Ca diet for 1 week and then switched to a low-calcium diet containing 0.02% Ca for an additional 3 weeks. Test compounds were given intraperitoneally at 130 and 325 pmol/day for 7 days. All doses were administered in 0.1 mL of propylene glycol/ethanol (95:5). Controls received the vehicle. Determinations were made 24 h after the last dose. There were 5 rats per group.
19. (b) Sicinski, R. R.; Perlman, K. L.; Prahl, J.; Smith, C.; DeLuca, H. F. J. Med. Chem. 1996, 39, 4497-4506.
20. Suda, T.; DeLuca, H. F.; Tanaka, Y. J. Nutr. 1970, 100, 1049-1052.
21. 13. (a) Renaud, J.-P.; Rochel, N.; Ruff, M.; Vivat, V.; Chambon, P.; Gronemeyer, H.; Moras, D. Nature, 1995, 378, 681-689.
22. (b) Bourguet, W.; Ruff, M.; Chambon, P.; Gronemeyer, H.; Moras, D. Nature, 1995, 375, 377-382.
23. (c) Wagner, R. L.; Apriletti, J. W.; McGrath, M. E.; West, B. L.; Baxter, J. D.; Fletterick, R. J. Nature, 1995, 378, 690-697.
24. (d) Nolte, R. T.; Wisely, G. B.; Westin, S.; Cobb, J. E.; Lambert, M. H.; Kurokawa, R.; Rosenfeld, M. G.; Willson, T. M.; Glass, C. K.; Milburn, M. V. Nature, 1998, 395, 137-143.
25. (e) Williams, S. P.; Sigler, P. B. Nature, 1998, 393, 392-396.
26. (f) Tanenbaum, D. M.; Wang, Y.; Williams, S. P.; Sigler, P. B. Proc. Natl. Acad. Sci. USA, 1998, 95, 5998-6003.