ACS Publications. Most Trusted. Most Cited. Most Read
My Activity

Crystal Structures of the Vitamin D Nuclear Receptor Liganded with the Vitamin D Side Chain Analogues Calcipotriol and Seocalcitol, Receptor Agonists of Clinical Importance. Insights into a Structural Basis for the Switching of Calcipotriol to a Receptor Antagonist by Further Side Chain Modification

View Author Information
Département de Biologie et de Génomique Structurales, IGBMC, CNRS/INSERM/Université Louis Pasteur, Parc d'Innovation BP10142, 67404 Illkirch Cedex, France
Cite this: J. Med. Chem. 2004, 47, 8, 1956–1961
Publication Date (Web):March 13, 2004
Copyright © 2004 American Chemical Society

    Article Views





    Other access options


    Abstract Image

    The plethora of actions of 1α,25(OH)2D3 in various systems suggested wide clinical applications of vitamin D nuclear receptor (VDR) ligands in treatments of inflammation, dermatological indication, osteoporosis, cancers, and autoimmune diseases. More than 3000 vitamin D analogues have been synthesized in order to reduce the calcemic side effects while maintaining the transactivation potency of these ligands. Here, we report the crystal structures of VDR ligand binding domain bound to two vitamin D agonists of therapeutical interest, calcipotriol and seocalcitol, which are characterized by their side chain modifications. These structures show the conservation of the VDR structure and the adaptation of the side chain anchored by hydroxyl moieties. The structure of VDR-calcipotriol helps us to understand the structural basis for for the switching of calcipotriol to a receptor antagonist by further side chain modification. The VDR-seocalcitol structure, in comparison with the structure of VDR-KH1060, a superagonist ligand closely related to seocalcitol, shows adaptation of the D ring and position of C-21 in order to adapt its more rigid side chain.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.


    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.


     These authors contributed equally to this work.

     Present address:  Istituto di Genetica Molecolare, Consiglio Nazionale delle Ricerche, Via Abbiategrasso 207, I-27100 Pavia, Italy, and Istituto di Biologia Cellulare, Consiglio Nazionale delle Ricerche, Campus A, Buzzati-Traverso, Via Ramarini, 32, 00016 Monterotondo Scalo, Rome, Italy.


     To whom correspondence should be addressed. Phone:  (33) 3 88 65 33 51. Fax:  (33) 3 88 65 32 76. E-mail:  [email protected].

    Cited By

    This article is cited by 96 publications.

    1. Juan Alcantara, Kelley Chiu, John D. Bickel, Robert C. Rizzo, Carlos Simmerling. Rapid Rescoring and Refinement of Ligand–Receptor Complexes Using Replica Exchange Molecular Dynamics with a Monte Carlo Pose Reservoir. Journal of Chemical Theory and Computation 2023, 19 (21) , 7934-7945.
    2. Xiangqian Li, Xiaowei Li, Fang Liu, Shuo Li, Dayong Shi. Rational Multitargeted Drug Design Strategy from the Perspective of a Medicinal Chemist. Journal of Medicinal Chemistry 2021, 64 (15) , 10581-10605.
    3. Anna Y. Belorusova, Sandra Chalhoub, Daniela Rovito, Natacha Rochel. Structural Analysis of VDR Complex with ZK168281 Antagonist. Journal of Medicinal Chemistry 2020, 63 (17) , 9457-9463.
    4. Miguel A. Maestro, Ferdinand Molnár, Carsten Carlberg. Vitamin D and Its Synthetic Analogs. Journal of Medicinal Chemistry 2019, 62 (15) , 6854-6875.
    5. Makoto Nakabayashi, Yoshito Tsukahara, Yukiko Iwasaki-Miyamoto, Mika Mihori-Shimazaki, Sachiko Yamada, Satomi Inaba, Masayuki Oda, Masato Shimizu, Makoto Makishima, Hiroaki Tokiwa, Teikichi Ikura, and Nobutoshi Ito . Crystal Structures of Hereditary Vitamin D-Resistant Rickets-Associated Vitamin D Receptor Mutants R270L and W282R Bound to 1,25-Dihydroxyvitamin D3 and Synthetic Ligands. Journal of Medicinal Chemistry 2013, 56 (17) , 6745-6760.
    6. Nobuko Yoshimoto, Yuta Sakamaki, Minoru Haeta, Akira Kato, Yuka Inaba, Toshimasa Itoh, Makoto Nakabayashi, Nobutoshi Ito, and Keiko Yamamoto . Butyl Pocket Formation in the Vitamin D Receptor Strongly Affects the Agonistic or Antagonistic Behavior of Ligands. Journal of Medicinal Chemistry 2012, 55 (9) , 4373-4381.
    7. María A. Regueira, Shaonly Samanta, Peter J. Malloy, Paloma Ordóñez-Morán, Diana Resende, Fredy Sussman, Alberto Muñoz, Antonio Mouriño, David Feldman, and Mercedes Torneiro . Synthesis and Biological Evaluation of 1α,25-Dihydroxyvitamin D3 Analogues Hydroxymethylated at C-26. Journal of Medicinal Chemistry 2011, 54 (11) , 3950-3962.
    8. Yuta Sakamaki, Yuka Inaba, Nobuko Yoshimoto and Keiko Yamamoto . Potent Antagonist for the Vitamin D Receptor: Vitamin D Analogues with Simple Side Chain Structure. Journal of Medicinal Chemistry 2010, 53 (15) , 5813-5826.
    9. Pierre Antony, Rita Sigüeiro, Tiphaine Huet, Yoshiteru Sato, Nick Ramalanjaona, Luis Cezar Rodrigues, Antonio Mouriño, Dino Moras and Natacha Rochel . Structure−Function Relationships and Crystal Structures of the Vitamin D Receptor Bound 2α-Methyl-(20S,23S)- and 2α-Methyl-(20S,23R)-epoxymethano-1α,25-dihydroxyvitamin D3. Journal of Medicinal Chemistry 2010, 53 (3) , 1159-1171.
    10. Agnieszka Glebocka, Katarzyna Sokolowska, Rafal R. Sicinski, Lori A. Plum and Hector F. DeLuca. New 1α,25-Dihydroxy-19-norvitamin D3 Compounds Constrained in a Single A-Ring Conformation: Synthesis of the Analogues by Ring-Closing Metathesis Route and Their Biological Evaluation. Journal of Medicinal Chemistry 2009, 52 (11) , 3496-3504.
    11. Yuka Inaba, Nobuko Yoshimoto, Yuta Sakamaki, Makoto Nakabayashi, Teikichi Ikura, Hirokazu Tamamura, Nobutoshi Ito, Masato Shimizu and Keiko Yamamoto . A New Class of Vitamin D Analogues that Induce Structural Rearrangement of the Ligand-Binding Pocket of the Receptor. Journal of Medicinal Chemistry 2009, 52 (5) , 1438-1449.
    12. Makoto Nakabayashi, Sachiko Yamada, Nobuko Yoshimoto, Takashi Tanaka, Miharu Igarashi, Teikichi Ikura, Nobutoshi Ito, Makoto Makishima, Hiroaki Tokiwa, Hector F. DeLuca and Masato Shimizu. Crystal Structures of Rat Vitamin D Receptor Bound to Adamantyl Vitamin D Analogs: Structural Basis for Vitamin D Receptor Antagonism and Partial Agonism. Journal of Medicinal Chemistry 2008, 51 (17) , 5320-5329.
    13. Rafal R. Sicinski,, Agnieszka Glebocka,, Lori A. Plum, and, Hector F. DeLuca. Design, Synthesis, and Biological Evaluation of a 1α,25-Dihydroxy-19-norvitamin D3 Analogue with a Frozen A-Ring Conformation. Journal of Medicinal Chemistry 2007, 50 (24) , 6154-6164.
    14. Michael J. Hartshorn,, Marcel L. Verdonk,, Gianni Chessari,, Suzanne C. Brewerton,, Wijnand T. M. Mooij,, Paul N. Mortenson, and, Christopher W. Murray. Diverse, High-Quality Test Set for the Validation of Protein−Ligand Docking Performance. Journal of Medicinal Chemistry 2007, 50 (4) , 726-741.
    15. Shinji Hourai,, Toshie Fujishima,, Atsushi Kittaka,, Yoshitomo Suhara,, Hiroaki Takayama,, Natacha Rochel, and, Dino Moras. Probing a Water Channel near the A-Ring of Receptor-Bound 1α,25-Dihydroxyvitamin D3 with Selected 2α-Substituted Analogues. Journal of Medicinal Chemistry 2006, 49 (17) , 5199-5205.
    16. Yusuke Nakano,, Yuko Kato,, Keisuke Imai,, Eiji Ochiai,, Jun-ichi Namekawa,, Seiichi Ishizuka,, Kazuya Takenouchi,, Aya Tanatani,, Yuichi Hashimoto, and, Kazuo Nagasawa. Practical Synthesis and Evaluation of the Biological Activities of 1α,25-dihydroxyvitamin D3 Antagonists, 1α,25-dihydroxyvitamin D3-26,23-lactams. Designed on the Basis of the Helix 12-Folding Inhibition Hypothesis. Journal of Medicinal Chemistry 2006, 49 (8) , 2398-2406.
    17. Xosé C. González-Avión,, Antonio Mouriño,, Natacha Rochel, and, Dino Moras. Novel 1α,25-Dihydroxyvitamin D3 Analogues with the Side Chain at C12. Journal of Medicinal Chemistry 2006, 49 (5) , 1509-1516.
    18. Keiko Yamamoto,, Daijiro Abe,, Nobuko Yoshimoto,, Mihwa Choi,, Kenji Yamagishi,, Hiroaki Tokiwa,, Masato Shimizu,, Makoto Makishima, and, Sachiko Yamada. Vitamin D Receptor:  Ligand Recognition and Allosteric Network. Journal of Medicinal Chemistry 2006, 49 (4) , 1313-1324.
    19. Anuj Gahlawat, Anjali Singh, Hardeep Sandhu, Prabha Garg. CRAFT: a web-integrated cavity prediction tool based on flow transfer algorithm. Journal of Cheminformatics 2024, 16 (1)
    20. J. Wesley Pike, Seong Min Lee, Nancy A. Benkusky, Mark B. Meyer. Genome-wide perspectives on vitamin D receptor actions. 2024, 213-228.
    21. Kazuki Maekawa, Michiyasu Ishizawa, Takashi Ikawa, Hironao Sajiki, Taro Matsumoto, Hiroaki Tokiwa, Makoto Makishima, Sachiko Yamada. Syntheses of 25-Adamantyl-25-alkyl-2-methylidene-1α,25-dihydroxyvitamin D3 Derivatives with Structure–Function Studies of Antagonistic and Agonistic Active Vitamin D Analogs. Biomolecules 2023, 13 (7) , 1082.
    22. Ettayapuram Ramaprasad Azhagiya Singam, Kathleen A. Durkin, Michele A. La Merrill, J. David Furlow, Jen-Chywan Wang, Martyn T. Smith. The vitamin D receptor as a potential target for the toxic effects of per- and polyfluoroalkyl substances (PFASs): An in-silico study. Environmental Research 2023, 217 , 114832.
    23. John Wesley Pike, Mark B. Meyer. New Approaches to Assess Mechanisms of Action of Selective Vitamin D Analogues. International Journal of Molecular Sciences 2021, 22 (22) , 12352.
    24. Chao Shen, Ye Hu, Zhe Wang, Xujun Zhang, Jinping Pang, Gaoang Wang, Haiyang Zhong, Lei Xu, Dongsheng Cao, Tingjun Hou. Beware of the generic machine learning-based scoring functions in structure-based virtual screening. Briefings in Bioinformatics 2021, 22 (3)
    25. Kouta Ibe, Takeshi Yamada, Sentaro Okamoto. Synthesis and vitamin D receptor affinity of 16-oxa vitamin D 3 analogues. Organic & Biomolecular Chemistry 2019, 17 (48) , 10188-10200.
    26. Guolin Zhao, Muhanad Elhafiz, Jingwei Jiang, Debanjan Das, Zhijian Li, Wang Zhou, Sisi Fan, Changling Wang, Ziqiao Yuan, Dengqiu Xu, Zhenzhou Jiang, Luyong Zhang, Tao Wang. Adaptive homeostasis of the vitamin D–vitamin D nuclear receptor axis in 8-methoxypsoralen-induced hepatotoxicity. Toxicology and Applied Pharmacology 2019, 362 , 150-158.
    27. Debabrata Mahapatra, Jill A. Franzosa, Kyle Roell, Melaine Agnes Kuenemann, Keith A. Houck, David M. Reif, Denis Fourches, Seth W. Kullman. Confirmation of high-throughput screening data and novel mechanistic insights into VDR-xenobiotic interactions by orthogonal assays. Scientific Reports 2018, 8 (1)
    28. Oleg Borbulevych, Roger I. Martin, Lance M. Westerhoff. High-throughput quantum-mechanics/molecular-mechanics (ONIOM) macromolecular crystallographic refinement with PHENIX / DivCon : the impact of mixed Hamiltonian methods on ligand and protein structure. Acta Crystallographica Section D Structural Biology 2018, 74 (11) , 1063-1077.
    29. Brian Hie, Hyunghoon Cho, Bonnie Berger. Realizing private and practical pharmacological collaboration. Science 2018, 362 (6412) , 347-350.
    30. Maged Saleh, Christoph Welsch, Chengcong Cai, Claudia Döring, Jérôme Gouttenoire, Judith Friedrich, Katrin Haselow, Christoph Sarrazin, Klaus Badenhoop, Darius Moradpour, Stefan Zeuzem, Sabrina Rueschenbaum, Christian M. Lange. Differential modulation of hepatitis C virus replication and innate immune pathways by synthetic calcitriol-analogs. The Journal of Steroid Biochemistry and Molecular Biology 2018, 183 , 142-151.
    31. Makoto Makishima, Sachiko Yamada. Bile Acid-Derived Vitamin D Receptor Ligands. 2018, 629-646.
    32. Toshio Matsumoto, Fumiaki Takahashi. Eldecalcitol and Osteoporosis. 2018, 695-707.
    33. Aylin Viviana Silva-Ortiz, Eugene Bratoeff, María Teresa Ramírez-Apan, Rocío García-Becerra, David Ordaz-Rosado, Nancy Noyola-Martínez, Rafael Castillo-Bocanegra, David Barrera. Synthesis and biological activity of two pregnane derivatives with a triazole or imidazole ring at C-21. The Journal of Steroid Biochemistry and Molecular Biology 2016, 159 , 8-18.
    34. Teikichi Ikura, Nobutoshi Ito. Crystal Structure of the Vitamin D Receptor Ligand-Binding Domain with Lithocholic Acids. 2016, 117-136.
    35. Sylvia Christakos, Puneet Dhawan, Annemieke Verstuyf, Lieve Verlinden, Geert Carmeliet. Vitamin D: Metabolism, Molecular Mechanism of Action, and Pleiotropic Effects. Physiological Reviews 2016, 96 (1) , 365-408.
    36. Maura Malinska, Andrzej Kutner, Krzysztof Woźniak. Predicted structures of new Vitamin D Receptor agonists based on available X-ray structures. Steroids 2015, 104 , 220-229.
    37. MAGDALENA MILCZAREK, BEATA FILIP-PSURSKA, WIESŁAW ŚWIĘTNICKI, ANDRZEJ KUTNER, JOANNA WIETRZYK. Vitamin D analogs combined with 5-fluorouracil in human HT-29 colon cancer treatment. Oncology Reports 2014, 32 (2) , 491-504.
    38. Ferdinand Molnár. Structural considerations of vitamin D signaling. Frontiers in Physiology 2014, 5
    39. Jelena Vojinovic. Vitamin D receptor agonists’ anti‐inflammatory properties. Annals of the New York Academy of Sciences 2014, 1317 (1) , 47-56.
    40. Yoshiyuki Ono. Multifunctional and potent roles of the 3-hydroxypropoxy group provide eldecalcitol's benefit in osteoporosis treatment. The Journal of Steroid Biochemistry and Molecular Biology 2014, 139 , 88-97.
    41. Hiroyuki Masuno, Teikichi Ikura, Daisuke Morizono, Isamu Orita, Sachiko Yamada, Masato Shimizu, Nobutoshi Ito. Crystal structures of complexes of vitamin D receptor ligand-binding domain with lithocholic acid derivatives. Journal of Lipid Research 2013, 54 (8) , 2206-2213.
    42. Baojian Wu, Sha Li, Dong Dong. 3D structures and ligand specificities of nuclear xenobiotic receptors CAR, PXR and VDR. Drug Discovery Today 2013, 18 (11-12) , 574-581.
    43. Thomas P. Burris, Laura A. Solt, Yongjun Wang, Christine Crumbley, Subhashis Banerjee, Kristine Griffett, Thomas Lundasen, Travis Hughes, Douglas J. Kojetin, . Nuclear Receptors and Their Selective Pharmacologic Modulators. Pharmacological Reviews 2013, 65 (2) , 710-778.
    44. Jinge Zhu, Hongyu Rao, Marco Tonelli, William M. Westler, Kiran K. Singarapu, John L. Markley, Hector F. DeLuca, Fariba M. Assadi-Porter. Efficient stable isotope labeling and purification of vitamin D receptor from inclusion bodies. Protein Expression and Purification 2012, 85 (1) , 25-31.
    45. Carsten Carlberg, Ferdinand Molnár, Antonio Mouriño. Vitamin D receptor ligands: the impact of crystal structures. Expert Opinion on Therapeutic Patents 2012, 22 (4) , 417-435.
    46. Ramón Fraga, Flavia Zacconi, Fredy Sussman, Paloma Ordóñez‐Morán, Alberto Muñoz, Tiphaine Huet, Ferdinand Molnár, Dino Moras, Natacha Rochel, Miguel Maestro, Antonio Mouriño. Design, Synthesis, Evaluation, and Structure of Vitamin D Analogues with Furan Side Chains. Chemistry – A European Journal 2012, 18 (2) , 603-612.
    47. J.Wesley Pike, Mark B. Meyer. 1,25-Dihydroxyvitamin D3. 2012, 1681-1709.
    48. Jinhu Wang, Ke Tang, Qianqian Hou, Xueli Cheng, Yongjun Liu, Chengbu Liu. Theoretical studies on the structural rearrangement of ligand binding pocket in human vitamin D receptor. International Journal of Quantum Chemistry 2011, 111 (14) , 3928-3937.
    49. Amanda M. Ousley, Hilda S. Castillo, Anna Duraj-Thatte, Donald F. Doyle, Bahareh Azizi. A human vitamin D receptor mutant activated by cholecalciferol. The Journal of Steroid Biochemistry and Molecular Biology 2011, 125 (3-5) , 202-210.
    50. J. Wesley Pike, Mark B. Meyer, Seong Min Lee. The Vitamin D Receptor. 2011, 97-135.
    51. Natacha Rochel, Dino Moras. Structural Basis for Ligand Activity in VDR. 2011, 171-191.
    52. Makoto Makishima, Sachiko Yamada. The Bile Acid Derivatives Lithocholic Acid Acetate and Lithocholic Acid Propionate are Functionally Selective Vitamin D Receptor Ligands. 2011, 1509-1524.
    53. Jun Zhang, Michael J. Chalmers, Keith R. Stayrook, Lorri L. Burris, Ruben D. Garcia-Ordonez, Bruce D. Pascal, Thomas P. Burris, Jeffery A. Dodge, Patrick R. Griffin. Hydrogen/Deuterium Exchange Reveals Distinct Agonist/Partial Agonist Receptor Dynamics within Vitamin D Receptor/Retinoid X Receptor Heterodimer. Structure 2010, 18 (10) , 1332-1341.
    54. Sayaka Motoyoshi, Kenji Yamagishi, Sachiko Yamada, Hiroaki Tokiwa. Ligand-dependent conformation change reflects steric structure and interactions of a vitamin D receptor/ligand complex: A fragment molecular orbital study. The Journal of Steroid Biochemistry and Molecular Biology 2010, 121 (1-2) , 56-59.
    55. Wanda Sicinska, Mateusz Kurcinski. MSITE: A new computational tool for comparison of homological proteins in holo form. The Journal of Steroid Biochemistry and Molecular Biology 2010, 121 (1-2) , 34-42.
    56. Yan-Ru Lou, Ferdinand Molnár, Mikael Peräkylä, Shengjun Qiao, Allan V. Kalueff, René St-Arnaud, Carsten Carlberg, Pentti Tuohimaa. 25-Hydroxyvitamin D3 is an agonistic vitamin D receptor ligand. The Journal of Steroid Biochemistry and Molecular Biology 2010, 118 (3) , 162-170.
    57. Lori A. Plum, Hector F. DeLuca. The Functional Metabolism and Molecular Biology of Vitamin D Action. 2010, 61-97.
    58. Mathew T. Mizwicki, Craig M. Bula, Paween Mahinthichaichan, Helen L. Henry, Seiichi Ishizuka, Anthony W. Norman. On the Mechanism Underlying (23S)-25-Dehydro-1α(OH)-vitamin D3-26,23-lactone Antagonism of hVDRwt Gene Activation and Its Switch to a Superagonist. Journal of Biological Chemistry 2009, 284 (52) , 36292-36301.
    59. Mathew T. Mizwicki, Anthony W. Norman. The Vitamin D Sterol–Vitamin D Receptor Ensemble Model Offers Unique Insights into Both Genomic and Rapid-Response Signaling. Science Signaling 2009, 2 (75)
    60. Taner Kaya, Narasimha Swamy, Kelly S. Persons, Swapna Ray, Scott C. Mohr, Rahul Ray. Covalent labeling of nuclear vitamin D receptor with affinity labeling reagents containing a cross-linking probe at three different positions of the parent ligand: Structural and biochemical implications. Bioorganic Chemistry 2009, 37 (2) , 57-63.
    61. Lori A. Plum, Hector F. DeLuca. The Functional Metabolism and Molecular Biology of Vitamin D Action. Clinical Reviews in Bone and Mineral Metabolism 2009, 7 (1) , 20-41.
    62. Elżbieta Gocek, Marek Kiełbiński, Paulina Wyłób, Andrzej Kutner, Ewa Marcinkowska. Side-chain modified vitamin D analogs induce rapid accumulation of VDR in the cell nuclei proportionately to their differentiation-inducing potential. Steroids 2008, 73 (14) , 1359-1366.
    63. Sean Ekins, Erica J Reschly, Lee R Hagey, Matthew D Krasowski. Evolution of pharmacologic specificity in the pregnane X receptor. BMC Evolutionary Biology 2008, 8 (1)
    64. Kaori Cho, Fumito Uneuchi, Yuko Kato-Nakamura, Jun-ichi Namekawa, Seiichi Ishizuka, Kazuya Takenouchi, Kazuo Nagasawa. Structure–activity relationship studies on vitamin D lactam derivatives as vitamin D receptor antagonist. Bioorganic & Medicinal Chemistry Letters 2008, 18 (15) , 4287-4290.
    65. Masato Shimizu, Yukiko Miyamoto, Hajime Takaku, Mayumi Matsuo, Makoto Nakabayashi, Hiroyuki Masuno, Nobuyuki Udagawa, Hector F. DeLuca, Teikichi Ikura, Nobutoshi Ito. 2-Substituted-16-ene-22-thia-1α,25-dihydroxy-26,27-dimethyl-19-norvitamin D3 analogs: Synthesis, biological evaluation, and crystal structure. Bioorganic & Medicinal Chemistry 2008, 16 (14) , 6949-6964.
    66. Luz E. Tavera-Mendoza, Tan D. Quach, Basel Dabbas, Jonathan Hudon, Xiaohong Liao, Ana Palijan, James L. Gleason, John H. White. Incorporation of histone deacetylase inhibition into the structure of a nuclear receptor agonist. Proceedings of the National Academy of Sciences 2008, 105 (24) , 8250-8255.
    67. Shinji Hourai, Luis Cezar Rodrigues, Pierre Antony, Bernardo Reina-San-Martin, Fabrice Ciesielski, Benjamin Claude Magnier, Kristina Schoonjans, Antonio Mouriño, Natacha Rochel, Dino Moras. Structure-Based Design of a Superagonist Ligand for the Vitamin D Nuclear Receptor. Chemistry & Biology 2008, 15 (4) , 383-392.
    68. Anthony W. Norman. 1α,25(OH)2 Vitamin D3Vitamin D Nuclear Receptor (VDR) and Plasma Vitamin D-Binding Protein (DBP) Structures and Ligand Shape Preferences for Genomic and Rapid Biological Responses. 2008, 749-778.
    69. Nobuko Yoshimoto, Yuka Inaba, Sachiko Yamada, Makoto Makishima, Masato Shimizu, Keiko Yamamoto. 2-Methylene 19-nor-25-dehydro-1α-hydroxyvitamin D3 26,23-lactones: Synthesis, biological activities and molecular basis of passive antagonism. Bioorganic & Medicinal Chemistry 2008, 16 (1) , 457-473.
    70. Angela K. Ormerod, Zhenlan Xing, Nancy G. Pedigo, Anjali Mishra, David M. Kaetzel. THE CALCITRIOL ANALOGUE EB1089 IMPAIRS ALVEOLARIZATION AND INDUCES LOCALIZED REGIONS OF INCREASED FIBROBLAST DENSITY IN NEONATAL RAT LUNG. Experimental Lung Research 2008, 34 (4) , 155-182.
    71. Atsushi KITTAKA. Structural Refinement of seco-Steroidal Skeleton and the Biological Activity through Nuclear Receptors. YAKUGAKU ZASSHI 2008, 128 (9) , 1235-1250.
    72. Erica J Reschly, Afonso Celso Dias Bainy, Jaco Joaquim Mattos, Lee R Hagey, Nathan Bahary, Sripal R Mada, Junhai Ou, Raman Venkataramanan, Matthew D Krasowski. Functional evolution of the vitamin D and pregnane X receptors. BMC Evolutionary Biology 2007, 7 (1)
    73. Carsten Carlberg, Sabine Seuter. The Vitamin D Receptor. Dermatologic Clinics 2007, 25 (4) , 515-523.
    74. Miharu Igarashi, Nobuko Yoshimoto, Keiko Yamamoto, Masato Shimizu, Michiyasu Ishizawa, Makoto Makishima, Hector F. DeLuca, Sachiko Yamada. Identification of a highly potent vitamin D receptor antagonist: (25S)-26-Adamantyl-25-hydroxy-2-methylene-22,23-didehydro-19,27-dinor-20-epi-vitamin D3 (ADMI3). Archives of Biochemistry and Biophysics 2007, 460 (2) , 240-253.
    75. Lee A. Zella, Ching-Yi Chang, Donald P. McDonnell, J. Wesley Pike. The vitamin D receptor interacts preferentially with DRIP205-like LxxLL motifs. Archives of Biochemistry and Biophysics 2007, 460 (2) , 206-212.
    76. Natacha Rochel, Shinji Hourai, Xenxo Pérez-García, Antonio Rumbo, Antonio Mourino, Dino Moras. Crystal structure of the vitamin D nuclear receptor ligand binding domain in complex with a locked side chain analog of calcitriol. Archives of Biochemistry and Biophysics 2007, 460 (2) , 172-176.
    77. Fabrice Ciesielski, Natacha Rochel, Dino Moras. Adaptability of the Vitamin D nuclear receptor to the synthetic ligand Gemini: Remodelling the LBP with one side chain rotation. The Journal of Steroid Biochemistry and Molecular Biology 2007, 103 (3-5) , 235-242.
    78. Mathew T. Mizwicki, Craig M. Bula, June E. Bishop, Anthony W. Norman. New insights into Vitamin D sterol-VDR proteolysis, allostery, structure–function from the perspective of a conformational ensemble model. The Journal of Steroid Biochemistry and Molecular Biology 2007, 103 (3-5) , 243-262.
    79. N.T. Zaveri, B.J. Murphy. Nuclear Hormone Receptors. 2007, 993-1036.
    80. Carolin Daniel, Heinfried H. Radeke, Nico A. Sartory, Nadine Zahn, Ulrich Zuegel, Andreas Steinmeyer, Jürgen Stein. The New Low Calcemic Vitamin D Analog 22-Ene-25-Oxa-Vitamin D Prominently Ameliorates T Helper Cell Type 1-Mediated Colitis in Mice. Journal of Pharmacology and Experimental Therapeutics 2006, 319 (2) , 622-631.
    81. Koji Takeda, Kaichiro Kominato, Atsuko Sugita, Yukiko Iwasaki, Mika Shimazaki, Masato Shimizu. Isolation and identification of 2α,25-dihydroxyvitamin D3, a new metabolite from Pseudonocardia autotrophica 100U-19 cells incubated with Vitamin D3. Steroids 2006, 71 (8) , 736-744.
    82. Ruth Sánchez‐Martínez, Ana I Castillo, Andreas Steinmeyer, Ana Aranda. The retinoid X receptor ligand restores defective signalling by the vitamin D receptor. EMBO reports 2006, 7 (10) , 1030-1034.
    83. Mika Shimazaki, Yukiko Miyamoto, Keiko Yamamoto, Sachiko Yamada, Masamichi Takami, Toshimasa Shinki, Nobuyuki Udagawa, Masato Shimizu. Analogs of 1α,25-dihydroxyvitamin D3 with high potency in induction of osteoclastogenesis and prevention of dendritic cell differentiation: Synthesis and biological evaluation of 2-substituted 19-norvitamin D analogs. Bioorganic & Medicinal Chemistry 2006, 14 (13) , 4645-4656.
    84. Masato Shimizu, Yukiko Miyamoto, Emi Kobayashi, Mika Shimazaki, Keiko Yamamoto, Wolfgang Reischl, Sachiko Yamada. Synthesis and biological activities of new 1α,25-dihydroxy-19-norvitamin D3 analogs with modifications in both the A-ring and the side chain. Bioorganic & Medicinal Chemistry 2006, 14 (12) , 4277-4294.
    85. Manisha Iyer, Erica J Reschly, Matthew D Krasowski. Functional evolution of the pregnane X receptor. Expert Opinion on Drug Metabolism & Toxicology 2006, 2 (3) , 381-397.
    86. Ferdinand Molnár, Mikael Peräkylä, Carsten Carlberg. Vitamin D Receptor Agonists Specifically Modulate the Volume of the Ligand-binding Pocket. Journal of Biological Chemistry 2006, 281 (15) , 10516-10526.
    87. Salimuddin Shah, Md Naimul Islam, Sivanesan Dakshanamurthy, Imran Rizvi, Mahadev Rao, Roger Herrell, Glendon Zinser, Meggan Valrance, Ana Aranda, Dino Moras, Anthony Norman, JoEllen Welsh, Stephen W. Byers. The Molecular Basis of Vitamin D Receptor and β-Catenin Crossregulation. Molecular Cell 2006, 21 (6) , 799-809.
    88. J. Wesley Pike, Makoto Watanuki, Nirupama K. Shevde. Vitamin D3: Synthesis, Actions, and Mechanisms in the Intestine and Colon. 2006, 1753-1771.
    89. James R. Hanson. Steroids: partial synthesis in medicinal chemistry. Nat. Prod. Rep. 2006, 23 (1) , 100-107.
    90. Matthew D Krasowski, Kazuto Yasuda, Lee R Hagey, Erin G Schuetz. Evolutionary selection across the nuclear hormone receptor superfamily with a focus on the NR1I subfamily (vitamin D, pregnane X, and constitutive androstane receptors). Nuclear Receptor 2005, 3 (1)
    91. Luciano Adorini, Susana Amuchastegui, Kenn C. Daniel. Prevention of chronic allograft rejection by Vitamin D receptor agonists. Immunology Letters 2005, 100 (1) , 34-41.
    92. R. E. Cachau, A. D. Podjarny. High-resolution crystallography and drug design. Journal of Molecular Recognition 2005, 18 (3) , 196-202.
    93. C. Daniel, T. Schlauch, U. Zügel, A. Steinmeyer, H. H. Radeke, D. Steinhilber, J. Stein. 22‐ene‐25‐oxa‐vitamin D: a new vitamin D analogue with profound immunosuppressive capacities. European Journal of Clinical Investigation 2005, 35 (5) , 343-349.
    94. Guy Eelen, Lieve Verlinden, Natacha Rochel, Frank Claessens, Pierre De Clercq, Maurits Vandewalle, Giuseppe Tocchini-Valentini, Dino Moras, Roger Bouillon, Annemieke Verstuyf. Superagonistic Action of 14-epi-Analogs of 1,25-Dihydroxyvitamin D Explained by Vitamin D Receptor-Coactivator Interaction. Molecular Pharmacology 2005, 67 (5) , 1566-1573.
    95. Peter W. Jurutka, Paul D. Thompson, G. Kerr Whitfield, Kristina R. Eichhorst, Neal Hall, Carlos Encinas Dominguez, Jui‐Cheng Hsieh, Carol A. Haussler, Mark R. Haussler. Molecular and functional comparison of 1,25‐dihydroxyvitamin D 3 and the novel vitamin D receptor ligand, lithocholic acid, in activating transcription of cytochrome P450 3A4. Journal of Cellular Biochemistry 2005, 94 (5) , 917-943.
    96. Masato Shimizu, Yukiko Iwasaki, Mika Shimazaki, Youhei Amano, Keiko Yamamoto, Wolfgang Reischl, Sachiko Yamada. New derivatives of 1α,25-dihydroxy-19-norvitamin D3 with two substituents at C-2: synthesis and biological activity. Bioorganic & Medicinal Chemistry Letters 2005, 15 (5) , 1451-1455.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Your Mendeley pairing has expired. Please reconnect