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Predicting the cell differentiation activity of 1 alpha,25-dihydroxyvitamin D3 side chain analogues from docking simulations

Sussman, F.; Rumbo, A.; Villaverde, M.C.; Mouriño, A.

Journal of Medicinal Chemistry 47(7): 1613-1616

2004

ISSN/ISBN: 0022-2623
PMID: 15027852
DOI: 10.1021/jm034157o
Accession: 049975394
We present a receptor-based protocol for the prediction of the cell differentiation activities of a series of side chain analogues of 1 alpha,25-dihydroxyvitamin D(3), a compound that exhibits a very large variety of biological functions. Our protocol is able to reproduce the activity of the compounds studied here. It also sheds light on the relative importance of binding site residues in the biological activity and on the mechanism behind it.

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Related References

Fujishima, T.; Zhaopeng, L.; Konno, K.; Nakagawa, K.; Okano, T.; Yamaguchi, K.; Takayama, H. 2001: Highly potent cell differentiation-inducing analogues of 1alpha,25-dihydroxyvitamin D3: synthesis and biological activity of 2-methyl-1,25-dihydroxyvitamin D3 with side-chain modifications Bioorganic and Medicinal Chemistry 9(2): 525-535
Suhara, Y.; Kittaka, A.; Kishimoto, S.; Calverley, M.J.; Fujishima, T.; Saito, N.; Sugiura, T.; Waku, K.; Takayama, H. 2002: Synthesis and testing of 2alpha-modified 1alpha,25-dihydroxyvitamin D(3) analogues with a double side chain: marked cell differentiation activity Bioorganic and Medicinal Chemistry Letters 12(22): 3255-3258
Marcinkowska, E.; Kutner, A.; Radzikowski, C. 1998: Cell differentiating and anti-proliferative activity of side-chain modified analogues of 1,25-dihydroxyvitamin D3 Journal of Steroid Biochemistry and Molecular Biology 67(1): 71-78
Saito, N.; Suhara, Y.; Kurihara, M.; Fujishima, T.; Honzawa, S.; Takayanagi, H.; Kozono, T.; Matsumoto, M.; Ohmori, M.; Miyata, N.; Takayama, H.; Kittaka, A. 2004: Design and efficient synthesis of 2 alpha-(omega-hydroxyalkoxy)-1 alpha,25-dihydroxyvitamin D3 Analogues, including 2-epi-ED-71 and their 20-epimers with HL-60 cell differentiation activity Journal of Organic Chemistry 69(22): 7463-7471
Craig, A.S.; Norman, A.W.; Okamura, W.H. 1992: Two novel allenic side chain analogues of 1 alpha 25 dihydroxyvitamin d 3 Journal of Organic Chemistry 57(16): 4374-4380
Perlman, K.L.; Kutner, A.; Schnoes, H.K.; Deluca, H.F. 1988: Novel convergent synthesis of side chain modified analogs of 1 25 dihydroxyvitamin d 3 with hl 60 cell differentiation activity Abstracts of Papers American Chemical Society 196: ORGN 337
Figadère, B.; Norman, A.W.; Henry, H.L.; Koeffler, H.P.; Zhou, J.Y.; Okamura, W.H. 1991: Arocalciferols: synthesis and biological evaluation of aromatic side-chain analogues of 1 alpha,25-dihydroxyvitamin D3(1a) Journal of Medicinal Chemistry 34(8): 2452-2463
Verlinden, L.; Verstuyf, A.; Eelen, G.; Bouillon, R.; Ordóñez-Morán, P.; Larriba, M.ía.J.ús.; Muñoz, A.; Rochel, N.; Sato, Y.; Moras, D.; Maestro, M.; Seoane, S.; Dominguez, F.; Eduardo-Canosa, S.; Nicoletti, D.; Moman, E.; Mouriño, A. 2011: Synthesis, structure, and biological activity of des-side chain analogues of 1α,25-dihydroxyvitamin D3 with substituents at C18 Chemmedchem 6(5): 788-793
Morimoto, S.; Imanaka, S.; Koh, E.; Shiraishi, T.; Nabata, T.; Kitano, S.; Miyashita, Y.; Nishii, Y.; Ogihara, T. 1989: Comparison of the inhibitions of proliferation of normal and psoriatic fibroblasts by 1 alpha,25-dihydroxyvitamin D3 and synthetic analogues of vitamin D3 with an oxygen atom in their side chain Biochemistry International 19(5): 1143-1149
Pérez-García, X.; Rumbo, A.; Larriba, Mía.Jesús.; Ordóñez, P.; Muñoz, A.; Mouriño, A. 2003: The first locked side-chain analogues of calcitriol (1alpha,25-dihydroxyvitamin D3) induce vitamin D receptor transcriptional activity Organic Letters 5(22): 4033-4036
Miyamoto, Y.; Shinki, T.; Yamamoto, K.; Ohyama, Y.; Iwasaki, H.; Hosotani, R.; Kasama, T.; Takayama, H.; Yamada, S.; Suda, T. 1997: 1-alpha,25-dihydroxyvitamin D-3-24-hydroxylase hydroxylates the carbon at the end of the side chain of the C-24-fluorinated analog of 1-alpha,25-dihydroxyvitamin D-3 Journal of Biological Chemistry 272(22): 14115-14119
Vrielynck, F.; Van Haver, D.; Vandewalle, M.; Verlinden, L.; Verstuyf, A.; Bouillon, R.; Croce, G.; De Clercq, P. 2009: Development of Analogues of la,25-Dihydroxyvitamin D3 with Biased Side-Chain Orientation : C20 Methylated Des-C,D-homo Analogues European Journal of Organic Chemistry (11): 1720-1737
Gabriëls, S.; Van Haver, D.; Vandewalle, M.; De Clercq, P.; Verstuyf, A.; Bouillon, R. 2001: Development of analogues of 1alpha,25-dihydroxyvitamin D3 with biased side chain orientation: methylated des-C,D-homo analogues Chemistry 7(2): 520-532
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Konno, K.; Ojima, K.; Hayashi, T.; Tanabe, M.; Takayama, H. 1997: Synthesis and biological activity of a 1 alpha,25-dihydroxyvitamin D2 analog bearing an amide group in the side-chain Chemical and Pharmaceutical Bulletin 45(1): 185-188