Biological activity and conformational analysis of C20 and C14 epimers of CD-ring modified trans-decalin 1α,25-dihydroxyvitamin D analogs

Journal of Steroid Biochemistry and Molecular Biology

Volumn 89-90, Issue , 2004, Pages 61-66

  De Clercq, Pierre J ^a   Murad, Ibrahim ^a   Gao, Ling Jie ^a   Chen, Yong Jun ^a   Van Haver, Dirk ^a   Vandewalle, Maurits ^a   Verstuyf, Annemieke ^b   Verlinden, Lieve ^b   Verboven, Christel ^b   Bouillon, Roger ^b  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Conformational analysis; Structure function relationships; Synthesis; Vitamin D

Indexed keywords

ALKADIENE; ALKENE DERIVATIVE; CALCITRIOL DERIVATIVE; DECALIN DERIVATIVE; DRUG METABOLITE;

ANIMAL EXPERIMENT; ANIMAL MODEL; CALCIUM BLOOD LEVEL; CELL PROLIFERATION; CELL STRAIN HL 60; CONFERENCE PAPER; CONFORMATION; CONTROLLED STUDY; DISSOCIATION; DRUG ACTIVITY; DRUG STRUCTURE; EPIMER; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; CALCITRIOL; MICE; SPECTRUM ANALYSIS;

EID: 3042638634     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2004.03.052     Document Type: Conference Paper

References (16)

1. A.W. Norman, R. Bouillon, M. Thomasset (Eds.), Proceedings of the Eleventh Workshop on vitamin D, University of California, Riverside, USA, 2000, pp. 1-992, and the previous 10 volumes in this series.
2. Bouillon R., Okamura W., Norman A.W. Structure-function relationships in the vitamin D endocrine system. Endocr. Rev. 16(2):1995;200-257
3. Chen Y.-J., Gao L.-J., Murad I., Verstuyf A., Verlinden L., Verboven C., Bouillon R., Viterbo D., Milanesio M., Van Haver D., Vandewalle M., De Clercq P.J. Synthesis, biological activity, and conformational analysis of CD-ring modified trans-decalin 1α, 25-dihydroxyvitamin D analogs. Org. Biomol. Chem. 1(2):2003;257-267
4. Verstuyf A., Verlinden L., Van Baelen H., Sabbe K., D'Halleweyn C., De Clercq P., Vandewalle M., Bouillon R. The biological activity of nonsteroidal vitamin D hormone analogs lacking both the C- and D-rings. J. Bone Miner. Res. 13(4):1998;549-558
5. Bouillon R., Van Baelen H., De Moor P. Comparative study of the affinity of the serum vitamin D-binding protein. J. Steroid Biochem. 13(9):1980;1029-1034
6. 3: preferential activity in inducing differentiation of human leukemia cells HL-60 in vitro. Proc. Natl. Acad. Sci. U.S.A. 84(9):1987;2610-2614
7. Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., Still W.C. MacroModel - an integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J. Comput. Chem. 11:1990;440-467
8. Okamura W.H., Palenzuela J.A., Plumet J., Midland M.M. Vitamin D: structure-function analyses and the design of analogs. J. Cell Biochem. 49:1992;10-18
9. Midland M.M., Plumet J., Okamura W.H. Effect of C20 stereochemistry on the conformational profile of the side chains of vitamin D analogs. Bioorg. Med. Chem. Lett. 3:1993;1799-1804
10. Van Haver D., De Clercq P.J. On the use of volume maps in the conformational analysis of vitamin D analogs. Bioorg. Med. Chem. Lett. 8(9):1998;1029-1034
11. 3 with biased side chain orientation: methylated des-C, D-homo analogues. Chem. Eur. J. 7(2):2001;520-532
12. Zhou X., Zhu G.-D., Van Haver D., Vandewalle M., De Clercq P.J., Verstuyf A., Bouillon R. Synthesis, biological activity, and conformational analysis of four seco-D-15, 19-bisnor-1α, 25-dihydroxyvitamin D analogues. J. Med. Chem. 42(18):1999;3539-3556
13. Yamada S., Yamamoto K., Masuno H., Choi M. Three-dimensional structure-function relationship of vitamin D and vitamin D receptor model. Steroids. 66(3-5):2001;177-187
14. Yamada S., Yamamoto K., Masuno H., Ohta M. Conformation-function relationship of vitamin D: conformational analysis predicts potential side chain structure. J. Med. Chem. 41(9):1998;1467-1475
15. 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(14):1996;2727-2737
16. 3 with a trans-fused decalin CD-ring has pronounced genomic activity, J. Biol. Chem. 278 (37) (2003) 35476-35482.