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Department of Biochemistry and Division of Biomedical Sciences, University of California Riverside, California 92521
Department of Chemistry, University of California Riverside, California 92521
Laboratorium voor Experimented, Geneeskunde en Endocrinologie, Katholieke Universiteit Leuven 3000 Leuven, Belgium
Correspondence: Address reprint requests to: Anthony W. Norman, Ph.D., Department of Biochemistry, University of California, Riverside, CA 92521
Abstract
I. Vitamin D Endocrine System: RESEARCH directed at defining the molecular mode of action of vitamin D is currently at its apex. There is now evidence implicating the essential involvement of vitamin D metabolites in a host of cellular processes, including calcium homeostasis, immunology, cell differentiation, and regulation of gene transcription. Further, there is evidence that the hormonally active form of vitamin D, 1
,25-dihydroxyvitamin D3 [1,25(OH)2D3], may generate biological responses via both regulation of gene transcription as well as via nongenomic pathways, some of which involve opening of voltage-gated Ca2+ channels. In addition, there are many examples of pathological disruption of the normal state in which a drug form of a vitamin D metabolite is proposed to be a (potentially) useful form of treatment, e.g. renal osteodystrophy, psoriasis, leukemia, breast cancer, and osteoporosis.
B. From vitamin to steroid hormone: The importance of the molecule vitamin D in the biological systems of higher animals has been recognized since its discovery by Mellanby in 1920 (1). It was in the interval of 1920–1930 that vitamin D officially became classified as a "vitamin" that was essential for the normal development of the skeleton and maintenance of Ca2+ homeostasis. The chemical structure of vitamin D was not determined until 1932 (2), and it was only then that it was apparent that this important nutritional substance was in reality a steroid, more specifically, a secosteroid, indicating that one of the rings of the cyclopentanoperhydrophenanthrene ring structure (the 9–10 carbon-carbon bond of ring B) was broken (see Section II).
Footnotes
* This work was supported by grants from the USPHS NIH, DK-09012 (AWN), DK-16,595 (WHO), CA-43,277 (AWN & WHO), and grants from the Belgian Foundation for Medical Research (FGWO 3.0044.89 and 3.0091.93 to RB).
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 J. Prudencio, N. Akutsu, N. Benlimame, T. Wang, Y. Bastien, R. Lin, M. J. Black, M. A. Alaoui-Jamali, and J. H. White Action of Low Calcemic 1{{alpha}},25-Dihydroxyvitamin D3 Analogue EB1089 in Head and Neck Squamous Cell Carcinoma J Natl Cancer Inst, May 16, 2001; 93(10): 745 - 753. [Abstract] [Full Text] [PDF]
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G. Tocchini-Valentini, N. Rochel, J. M. Wurtz, A. Mitschler, and D. Moras Crystal structures of the vitamin D receptor complexed to superagonist 20-epi ligands PNAS, May 8, 2001; 98(10): 5491 - 5496. [Abstract] [Full Text] [PDF]
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 J.-Y. Hsu, D. Feldman, J. E. McNeal, and D. M. Peehl Reduced 1{{alpha}}-hydroxylase Activity in Human Prostate Cancer Cells Correlates with Decreased Susceptibility to 25-Hydroxyvitamin D3-induced Growth Inhibition Cancer Res., April 1, 2001; 61(7): 2852 - 2856. [Abstract] [Full Text]
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M. Shiohara, M. Uskokovic, J. Hisatake, Y. Hisatake, K. Koike, A. Komiyama, and H. P. Koeffler 24-Oxo Metabolites of Vitamin D3 Analogues: Disassociation of Their Prominent Antileukemic Effects from Their Lack of Calcium Modulation Cancer Res., April 1, 2001; 61(8): 3361 - 3368. [Abstract] [Full Text]
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D. Zehnder, R. Bland, M. C. Williams, R. W. McNinch, A. J. Howie, P. M. Stewart, and M. Hewison Extrarenal Expression of 25-Hydroxyvitamin D3-1{{alpha}}-Hydroxylase J. Clin. Endocrinol. Metab., February 1, 2001; 86(2): 888 - 894. [Abstract] [Full Text]
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S. Ishizuka, D. Miura, K. Ozono, M. Chokki, H. Mimura, and A. W. Norman Antagonistic Actions in Vivo of (23S)-25-Dehydro-1{{alpha}}-Hydroxyvitamin D3-26,23-Lactone on Calcium Metabolism Induced by 1{{alpha}},25-Dihydroxyvitamin D3 Endocrinology, January 1, 2001; 142(1): 59 - 67. [Abstract] [Full Text] [PDF]
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 E. Falkenstein, H.-C. Tillmann, M. Christ, M. Feuring, and M. Wehling Multiple Actions of Steroid Hormones---A Focus on Rapid, Nongenomic Effects Pharmacol. Rev., December 1, 2000; 52(4): 513 - 556. [Abstract] [Full Text] [PDF]
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R. Mehta, M. Hawthorne, L. Uselding, D. Albinescu, R. Moriarty, K. Christov, and R. Mehta Prevention of N-Methyl-N-Nitrosourea-Induced Mammary Carcinogenesis in Rats by 1{alpha}-Hydroxyvitamin D5 J Natl Cancer Inst, November 15, 2000; 92(22): 1836 - 1840. [Abstract] [Full Text] [PDF]
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C. M. Bula, J. E. Bishop, S. Ishizuka, and A. W. Norman 25-Dehydro-1{alpha}-Hydroxyvitamin D3- 26,23S-Lactone Antagonizes the Nuclear Vitamin D Receptor by Mediating a Unique Noncovalent Conformational Change Mol. Endocrinol., November 1, 2000; 14(11): 1788 - 1796. [Abstract] [Full Text]
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Y. Bury, A. Steinmeyer, and C. Carlberg Structure Activity Relationship of Carboxylic Ester Antagonists of the Vitamin D3 Receptor Mol. Pharmacol., November 1, 2000; 58(5): 1067 - 1074. [Abstract] [Full Text]
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 H. Lilienthal, A. Fastabend, J. Hany, H. Kaya, A. Roth-Harer, L. Dunemann, and G. Winneke Reduced Levels of 1,25-Dihydroxyvitamin D3 in Rat Dams and Offspring after Exposure to a Reconstituted PCB Mixture Toxicol. Sci., October 1, 2000; 57(2): 292 - 301. [Abstract] [Full Text] [PDF]
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 I. Nemere, D. Larsson, and K. Sundell A specific binding moiety for 1,25-dihydroxyvitamin D3 in basal lateral membranes of carp enterocytes Am J Physiol Endocrinol Metab, September 1, 2000; 279(3): E614 - E621. [Abstract] [Full Text] [PDF]
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T. W. Kensler, P. M. Dolan, S. J. Gange, J.-K. Lee, Q. Wang, and G. H. Posner Conceptually new deltanoids (vitamin D analogs) inhibit multistage skin tumorigenesis Carcinogenesis, July 1, 2000; 21(7): 1341 - 1345. [Abstract] [Full Text] [PDF]
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M. Herdick, Y. Bury, M. Quack, M. R. Uskokovic, P. Polly, and C. Carlberg Response Element and Coactivator-Mediated Conformational Change of the Vitamin D3 Receptor Permits Sensitive Interaction with Agonists Mol. Pharmacol., June 1, 2000; 57(6): 1206 - 1217. [Abstract] [Full Text]
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L. Verlinden, A. Verstuyf, M. Van Camp, S. Marcelis, K. Sabbe, X.-Y. Zhao, Pierre De Clercq, M. Vandewalle, and R. Bouillon Two Novel 14-Epi-Analogues of 1,25-Dihydroxyvitamin D3 Inhibit the Growth of Human Breast Cancer Cells in Vitro and in Vivo Cancer Res., May 1, 2000; 60(10): 2673 - 2679. [Abstract] [Full Text]
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M. Lorentzon, R. Lorentzon, and P. Nordström Vitamin D Receptor Gene Polymorphism Is Associated with Birth Height, Growth to Adolescence, and Adult Stature in Healthy Caucasian Men: A Cross-Sectional and Longitudinal Study J. Clin. Endocrinol. Metab., April 1, 2000; 85(4): 1666 - 1671. [Abstract] [Full Text]
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K. Kinuta, H. Tanaka, T. Moriwake, K. Aya, S. Kato, and Y. Seino Vitamin D Is an Important Factor in Estrogen Biosynthesis of Both Female and Male Gonads Endocrinology, April 1, 2000; 141(4): 1317 - 1324. [Abstract] [Full Text] [PDF]
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M. Quack and C. Carlberg The Impact of Functional Vitamin D3 Receptor Conformations on DNA-Dependent Vitamin D3 Signaling Mol. Pharmacol., February 1, 2000; 57(2): 375 - 384. [Abstract] [Full Text]
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S. Puri, D. D. Bansal, M. R. Uskokovic, and R. R. MacGregor Induction of tissue plasminogen activator secretion from rat heart microvascular cells by fM 1,25(OH)2D3 Am J Physiol Endocrinol Metab, February 1, 2000; 278(2): E293 - E301. [Abstract] [Full Text] [PDF]
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M. Hotta, I. Fukuda, K. Sato, N. Hizuka, T. Shibasaki, and K. Takano The Relationship between Bone Turnover and Body Weight, Serum Insulin-Like Growth Factor (IGF) I, and Serum IGF-Binding Protein Levels in Patients with Anorexia Nervosa J. Clin. Endocrinol. Metab., January 1, 2000; 85(1): 200 - 206. [Abstract] [Full Text]
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 Z. Hmama, D. Nandan, L. Sly, K. L. Knutson, P. Herrera-Velit, and N. E. Reiner 1{alpha},25-Dihydroxyvitamin D3-Induced Myeloid Cell Differentiation Is Regulated by a Vitamin D Receptor-Phosphatidylinositol 3-Kinase Signaling Complex J. Exp. Med., December 6, 1999; 190(11): 1583 - 1594. [Abstract] [Full Text] [PDF]
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T. Inoue, J. Kamiyama, and T. Sakai Sp1 and NF-Y Synergistically Mediate the Effect of Vitamin D3 in the p27Kip1 Gene Promoter That Lacks Vitamin D Response Elements J. Biol. Chem., November 5, 1999; 274(45): 32309 - 32317. [Abstract] [Full Text] [PDF]
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K. Ozono, M. Saito, D. Miura, T. Michigami, S. Nakajima, and S. Ishizuka Analysis of the Molecular Mechanism for the Antagonistic Action of a Novel 1alpha ,25-Dihydroxyvitamin D3 Analogue toward Vitamin D Receptor Function J. Biol. Chem., November 5, 1999; 274(45): 32376 - 32381. [Abstract] [Full Text] [PDF]
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M. T. Cantorna, J. Humpal-Winter, and H. F. DeLuca Dietary Calcium Is a Major Factor in 1,25-Dihydroxycholecalciferol Suppression of Experimental Autoimmune Encephalomyelitis in Mice J. Nutr., November 1, 1999; 129(11): 1966 - 1971. [Abstract] [Full Text]
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M. Willheim, R. Thien, K. Schrattbauer, E. Bajna, M. Holub, R. Gruber, K. Baier, P. Pietschmann, W. Reinisch, O. Scheiner, et al. Regulatory Effects of 1{alpha},25-Dihydroxyvitamin D3 on the Cytokine Production of Human Peripheral Blood Lymphocytes J. Clin. Endocrinol. Metab., October 1, 1999; 84(10): 3739 - 3744. [Abstract] [Full Text] [PDF]
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D. M. Berry and K. A. Meckling-Gill Vitamin D Analogs, 20-Epi-22-Oxa-24a,26a,27a,-Trihomo-1{alpha},25(OH)2-Vitamin D3, 1,24(OH)2-22-Ene-24-Cyclopropyl-Vitamin D3 and 1{alpha},25(OH)2-Lumisterol3 Prime NB4 Leukemia Cells for Monocytic Differentiation via Nongenomic Signaling Pathways, Involving Calcium and Calpain Endocrinology, October 1, 1999; 140(10): 4779 - 4788. [Abstract] [Full Text]
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I. S. Mathiasen, U. Lademann, and M. Jaattela Apoptosis Induced by Vitamin D Compounds in Breast Cancer Cells Is Inhibited by Bcl-2 but Does Not Involve Known Caspases or p53 Cancer Res., October 1, 1999; 59(19): 4848 - 4856. [Abstract] [Full Text] [PDF]
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 P. Oelzner, S. Franke, A. Muller, G. Hein, and G. Stein Relationship between soluble markers of immune activation and bone turnover in post-menopausal women with rheumatoid arthritis Rheumatology, September 1, 1999; 38(9): 841 - 847. [Abstract] [Full Text] [PDF]
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R. G. Pestell, C. Albanese, A. T. Reutens, J. E. Segall, R. J. Lee, and A. Arnold The Cyclins and Cyclin-Dependent Kinase Inhibitors in Hormonal Regulation of Proliferation and Differentiation Endocr. Rev., August 1, 1999; 20(4): 501 - 534. [Abstract] [Full Text] [PDF]
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D. Miura, K. Manabe, K. Ozono, M. Saito, Q. Gao, A. W. Norman, and S. Ishizuka Antagonistic Action of Novel 1alpha ,25-Dihydroxyvitamin D3-26,23-lactone Analogs on Differentiation of Human Leukemia Cells (HL-60) Induced by 1alpha ,25-Dihydroxyvitamin D3 J. Biol. Chem., June 4, 1999; 274(23): 16392 - 16399. [Abstract] [Full Text] [PDF]
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A. Murayama, K.-i. Takeyama, S. Kitanaka, Y. Kodera, Y. Kawaguchi, T. Hosoya, and S. Kato Positive and Negative Regulations of the Renal 25-Hydroxyvitamin D3 1{alpha}-Hydroxylase Gene by Parathyroid Hormone, Calcitonin, and 1{alpha},25(OH)2D3 in Intact Animals Endocrinology, May 1, 1999; 140(5): 2224 - 2231. [Abstract] [Full Text]
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P. J. Malloy, J. W. Pike, and D. Feldman The Vitamin D Receptor and the Syndrome of Hereditary 1,25-Dihydroxyvitamin D-Resistant Rickets Endocr. Rev., April 1, 1999; 20(2): 156 - 188. [Abstract] [Full Text]
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S. H. Wang, R. J. Koenig, T. J. Giordano, A. Myc, N. W. Thompson, and J. R. Baker Jr. 1{alpha},25-Dihydroxyvitamin D3 Up-Regulates Bcl-2 Expression and Protects Normal Human Thyrocytes from Programmed Cell Death Endocrinology, April 1, 1999; 140(4): 1649 - 1656. [Abstract] [Full Text]
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 K.-I. Takeyama, Y. Masuhiro, H. Fuse, H. Endoh, A. Murayama, S. Kitanaka, M. Suzawa, J. Yanagisawa, and S. Kato Selective Interaction of Vitamin D Receptor with Transcriptional Coactivators by a Vitamin D Analog Mol. Cell. Biol., February 1, 1999; 19(2): 1049 - 1055. [Abstract] [Full Text] [PDF]
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E. Eklou-Kalonji, E. Zerath, C. Colin, C. Lacroix, X. Holy, I. Denis, and A. Pointillart Calcium-Regulating Hormones, Bone Mineral Content, Breaking Load and Trabecular Remodeling Are Altered in Growing Pigs Fed Calcium-Deficient Diets J. Nutr., January 1, 1999; 129(1): 188 - 193. [Abstract] [Full Text] [PDF]
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G. JONES, S. A. STRUGNELL, and H. F. DeLUCA Current Understanding of the Molecular Actions of Vitamin D Physiol Rev, October 1, 1998; 78(4): 1193 - 1231. [Abstract] [Full Text] [PDF]
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S. Peleg, C. Nguyen, B. T. Woodard, J.-K. Lee, and G. H. Posner Differential Use of Transcription Activation Function 2 Domain of the Vitamin D Receptor by 1,25-Dihydroxyvitamin D3 and Its A Ring-Modified Analogs Mol. Endocrinol., April 1, 1998; 12(4): 525 - 535. [Abstract] [Full Text]
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