Regulation of the Ferredoxin Component of Renal Hydroxylases at the Transcriptional and Postradiational Level and of the Protein Inhibitor of Cyclic AMP-Dependent Kinase

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1. Frontmatter I
2. FOREWORD V
3. Official Sponsors and Donors IX
4. YOUNG INVESTIGATOR AWARDEES NINTH WORKSHOP ON VITAMIN D X
5. Vitamin D Workshop. Career Recognition Awardees XI
6. Contents XIII
7. Chemistry of Vitamin D
8. Shape and Conformation of Vitamin D. 11-Fluoro-1a-Hydroxyvitamin D₃: The Quest for Experimental Evidence of the Folded Vitamin D Conformation 1
9. Conformation and Related Topological Features of Vitamin D: Structure-Function Relationships 12
10. Chemical Conversion of Vitamin D₃ to Calcitriol Lactone 21
11. Design, Synthesis, and SAR of Some 1-Substituted A-Ring Analogs of Calcitriol 25
12. A General Synthetic Route to A-Ring Hydroxylated Vitamin D Analogs from D-Pentoses 27
13. Retiferols. Design and Synthesis of the New Class of Vitamin D Analogs 29
14. Introduction of 1a-Hydroxyl Group to Provitamin D Causes New Photoisomerization Reactions 31
15. Synthesis and Determination of the Configurations of the 23-Hydroxylated Metabolites of Calcipotriol (MC 903) and their Epimers 33
16. Syntheses of Potential Inhibitors of 25-Hydroxyvitamin D₃-1a-Hydroxylase: A-Ring Analogs 35
17. Metallic Complexes of Hydroxylated Derivatives of Vitamin D₃ 37
18. A New Route to the Lythgoe-Roche's A-Ring Precursor of 1a,25-Dihydroxyvitamin D₃ 39
19. Structure-Activity Studies of Fluorinated Vitamin D Analogs 41
20. An In Vitro Model of Previtamin D Photosynthesis as Possible Monitor of Ozone Depletion 43
21. Synthesis of 24-Hydroxy-Vitamin D Analogues 45
22. Chromatographic Isolation and Spectroscopic Characterization of the Photoisomers of 1a,25-Dihydroxy-Provitamin D₃ 47
23. A New Route to the Vitamin D Triene System 49
24. Studies on the Synthesis of 19-Norprevitamin D₃ Analogues 51
25. Structure/Function Studies of Vitamin D Steroids
26. The Need for New Vitamin D Analogues: Mechanisms of Action and Clinical Applications 55
27. Future Prospects for Vitamin D Analogs 64
28. Chemistry and Biology of 22,23-yne Analogs of Calcitriol 73
29. Chemistry and Biology of 23-oxa-aro- and 23-thia-aro-Vitamin D Analogues with High Antiproliferative and Low Calcemic Activity 75
30. Activity of Vitamin D Analogs in Co-Transfected COS-7 Cells 77
31. Synthesis and Biological Character of 1β-Hydroxylated Vitamin D₃ Analogs 79
32. Biological Activity and Conformational Analysis of 1β,25-Dihydroxyvitamin D₃ and its Analogues 81
33. Topological Mimics of the 6-s-cis-Conformer of 1a,25-Dihydroxyvitamin D₃ Based on the Provitamin D Skeleton 83
34. Chemistry and Biology of Highly Active 22-oxy Analogs of 20-epi Calcitriol with Very Low Binding Affinity to the Vitamin D Recepto 85
35. New Discoveries in Vitamin D Related Compounds 87
36. Modelling of Previtamin D Photosynthesis in View of its Conformational Flexibility 89
37. Active Vitamin D Analogs with Side Chain Hydroxyl Group Occupying Diverse Spatial Region 91
38. Synthesis and Biological Activity of 23-oxa Vitamin D Analogues 93
39. Synthesis and Biological Activity of 20-Hydroxylated Vitamin D Analogues 95
40. 20-Methyl Vitamin D Analogues 97
41. 2β-Substituted Calcitriols and Other A-Ring Substituted Analogues - Synthesis and Biological Results 99
42. Syntheses and Biological Activity of 1ß-Substituted Active Vitamin D₃ Analogs 101
43. Vitamin D Binding Protein
44. Probing the Vitamin D-Sterol Binding Domain of Human Vitamin D-Binding Protein: Chemical Modification of Specific Amino Acid Residues 105
45. Crystallization and Preliminary X-Ray Investigation of Vitamin D-Binding Protein from Human Serum 107
46. Effects of Vitamin D-Binding Proteins on Biological Functions of 1 a,25-Dihydroxyvitamin D₃ Analogues 109
47. Vitamin D Hydroxylases: Biochemistry and Regulation
48. Differences of the Regulation of 24-Hydroxylase Gene Expression in the Kidney and Intestine 113
49. Regulation of the Ferredoxin Component of Renal Hydroxylases at the Transcriptional and Postradiational Level and of the Protein Inhibitor of Cyclic AMP-Dependent Kinase 122
50. Site and Rate of Hydroxylation of 1a-OH-D₃ Analogs by CYP27 Not Altered by Increasing Length or Changing Orientation of Vitamin D₃ Side Chain 131
51. Protein Kinase C Up-Regulates 1 a,25-Dihydroxyvitamin D₃-Induced Expression of 24-Hydroxylase Gene 133
52. IGF-I Restores the Age-Related Defect in Renal 1,25(OH)₂D₃ Biosynthesis in Response to Dietary Phosphorus Restriction in Rats 135
53. In Vitro Production of 1,25-Dihydroxyvitamin D₃ by Cultured Mouse Kidney Cells and its Regulation by Extracellular Phosphate and IGF-1 137
54. The Cytochromes P450 Catalyzing 25-Hydroxylation of Vitamin D and la-Hydroxy lation of 25-Hydroxyvitamin D₃ in Pig Liver 139
55. Evidence that 1a - and 27-Hydroxylation of 25-Hydroxyvitamin D₃ are Catalyzed by CYP27 in Pig Kidney Mitochondria 141
56. The Kinetics of Monocyte la-Hydroxy läse in Uremia. Modulation by Calcitriol and 25(OH)D₃ Therapy 143
57. Eicosanoid Inhibitor and Cytokine Regulation of 1,25(OH)₂D₃ Synthesis in Synovial Fluid Macrophages from Patients with Inflammatory Arthritis 145
58. 25-Hydroxyvitamin D-la-Hydroxy läse is Responsible for the Synthesis of 1.25-Dihydroxyvitamin D₃ by Peritoneal Macrophages of CAPD Treated Uremic Patients 147
59. Influence of Extracellular Calcium in the Kinetic Behaviour of 1-Hydroxylase (1-OHase) and 24-Hydroxylase (24-OHase) in Walker Carcinosarcoma 256 Cells (WS) and in the Renal Proximal Tube Phenotype Cells (LLC-PK1) 149
60. Insulin and Calcitonin Decrease the Expression of the Renal 25(OH)D-24- Hydroxylase Cytochrome P450 in Diabetic Rats 151
61. Continuous Activation of 25-Hydroxyvitamin D₃-24-Hydroxylase mRNA Expression by 1a,25-Dihydroxyvitamin D₃-3ß-Bromoacetate 153
62. Regulation of 24-Hydroxylase mRNA Expression by 1a,25(OH)₂D₃ and its Fluorinated Analogues 155
63. Comparative Effects of 1,25-Dihydroxyvitamin D₃ and EB 1089 on Murine 25-Hydroxyvitamin D₃-24-Hydroxylase 157
64. Vitamin D Metabolism and Catabolism
65. Target Cell Metabolism of Vitamin D and its Analogs 161
66. In Vivo Regulation of Rat Intestinal 24-Hydroxylase (I-24-OHase): Potential New Role of Calcitonin 170
67. Metabolism of 1a,25-Dihydroxyvitamin D₃ and One of its A-Ring Diastereomer 1a,25-Dihydroxy-3-Epivitamin D₃ in Neonatal Human Keratinocytes 172
68. Vitamin D Metabolism in Human Colon Adenocarcinoma-Derived Caco-2 Cells 174
69. Studies on Vitamin D Metabolism by a Human Small Cell Lung Cancer (SCLC) Cell Line, NCI-H82 176
70. The In Vitro Metabolism of Calcipotriol, 1,24(OH)₂D₃ and 1,25(OH)₂D₃ 178
71. Regulation of Tissue Inhibitor of Metalloproteinases (TIMP) by 1,25- and 24,25- Dihydroxyvitamin D₃ in the Rat Growth Plate 180
72. The Effect of Parathyroid Hormone on Renal 24-Hydroxylase Activity in the Isolated Perfused Rat Kidney 182
73. Steroidal Hormones as Modulators of Vitamin D Metabolism in Human Keratinocytes 184
74. Potentialisation of Vitamin D (Analogs) by Cytochrome P-450 Enzyme Inhibitors is Analog- and Cell-type Specific 186
75. Novel Cleavage of Vitamin D₂ Side Chain During Catabolism by Keratinocyte Cell Line 188
76. 22-Oxacalcitriol is Metabolized to C₂₁ Side-Chain-Cleaved Products in Both Liver and Target Cells 190
77. Metabolism of the 1a,25(OH)₂D₃ Analog 1a,25(OH)₂-16-ene-23-yne-D₃ in BALB/c Leukemic Mice and WEHI-3 Myeloid Leukemia Cells 192
78. Microtubules Mediate Cellular 25(OH)D₃ Traffic and the Response to 1,25(OH)₂D₃ in Human Monocytes 194
79. Study of the Metabolism of 1,25-Dihydroxy-16-ene-Vitamin D₃ in Rat Kidney Using On-line HPLC-Electrospray Tandem Mass Spectrometry 196
80. Human Placental Explants: An Efficient In Vitro Model for Comparative Metabolism of 1,25(OH)₂D₃ and its Synthetic Analogs 198
81. 24,25(OH)₂D₃ Modulates 1,25(OH)₂D₃ Metabolism in Human Osteoblasts 200
82. Metabolism of 25 Hydroxy Vitamin D₃: Kinetics of 23 and 24 Hydroxylases in Human Term Placenta 202
83. Comparative Study in Vitamin D Metabolism from the View-Point of Ontogeny and Phylogeny 204
84. Receptors for 1a,25(OH)₂D₃
85. Receptor Mediated Genomic Actions of 1,25(OH)₂D₃: Modulation by Phosphorylation 209
86. Modulation of Vitamin D₃ Target Gene Selectivity by Receptor Dimerization 217
87. The Molecular Basis for the Genomic Actions of the Vitamin D₃ Hormone 226
88. Expression of RXRa in Human Leukemic Cells During Differentiation Induced by All-Trans Retinoic Acid and 1a,25-Dihydroxyvitamin D 235
89. Differential Activation of the Vitamin D Receptor (VDR) by 1,25(OH)2- Vitamin D₃ and its 20-Epimers 237
90. Dopamine Activates Vitamin D Receptor But Not Retinoid Receptor Mediated Transcription 239
91. Ordered Binding of Human Vitamin D and Retinoid-X Receptor Complexes to Asymmetric Vitamin D-Responsive Elements 241
92. Immunohistochemical Localization of 1,25-Dihydroxy vitamin D₃ [1,25(OH)₂D₃] Receptors (VDR) in Human and Rat Pancreas 243
93. Structure-Function Relationship of Human Parathyroid Hormone on Vitamin D Receptor Regulation in Osteoblast-Like Cells (ROS 17/2.8) 245
94. Insulin-Like Growth Factor I Up-Regulates Intestinal 1,25(OH)₂D₃ Receptor in Phosphorus Restricted Rats 247
95. A Peptide C-Terminal to the Second Zn-Finger of Human Vitamin D Receptor is Able to Specify Nuclear Localization 249
96. Molecular Cloning and Sequencing of a Novel cDNA Related to the Steroid/Thyroid/Vitamin Family of Nuclear Receptors from a Vitamin DDeficient Chick Intestinal cDNA Library 251
97. Isolation and Analysis of cDNA Encoding a Naturally-Occurring Truncated Form of the Human Vitamin D Receptor 253
98. EB 1089, a Vitamin D Analogue, Induces the Vitamin D Receptor to Form Selective Receptor Complexes Depending on Cell Type 255
99. Gene Regulation
100. 1,25(OH)₂D₃ Response Elements: Is There an Order? 259
101. Vitamin D Regulation of Osteocalcin Gene Transcription: A Model for Defining Molecular Mechanisms of 1,25(OH)₂D₃ Control of Osteoblast Growth and Differentiation 264
102. Regulation of Integrin Expression by 1,25 Dihydroxyvitamin D₃ 273
103. Identification of a Chicken Intestinal DNA Binding Activity Not Related to the Vitamin D Receptor, but Capable of Specific Binding to Vitamin D Response Elements 282
104. Transcriptional Regulation of the Avian Mitochondrial Genome by Altered Dietary Vitamin D₃ Status: A Comparison of Intestinal and Kidney Responses 284
105. A Novel Vitamin D Response Element in the Murine c-fos Promoter 286
106. 1,25(OH)₂-Vitamin D3 (D3) Interactions with 3,5,3'-Triiodothyronine (T3) Signaling in 3 Osteosarcoma Cell Lines 288
107. 1,25(OH)₂-Vitamin D₃ (D₃) Signaling in HT-29 Cells: Interactions with 9-eis Retinoic Acid (9-eis RA) 290
108. Protein Inhibitor of Cyclic AMP-Dependent Protein Kinase: Genomic Cloning of a 1,25(OH)₂D₃ Down-Regulated Protein 292
109. Lack of 9-eis Retinoic Acid Effect on Renal 24-Hydroxylase mRNA Expression by 1,25-Dihydroxyvitamin D₃ In Vivo 294
110. Regulation of Osteopontin Expression by Calcitriol in Mouse Epidermal JB6 Cells 296
111. Dissociation between Regulation of Growth and C-myc Oncogen Expression by Vitamin D in Caco-2 Cells 298
112. TGF-ßl Inhibits the Induction of Osteocalcin Gene by 1,25(OH)₂D₃ at the Level of Transcription 300
113. Mechanism of Action of 1,25-Dihydroxyvitamin D Differs in Kidney, Intestine, and Bone Cell Lines 302
114. mRNA Levels of the Inhibitor Protein of cAMP-Dependent Protein Kinase are Regulated by 1,25(OH)₂D₃ and Forskolin 304
115. Vitamin D Receptor (VDR) Interactions with Vitamin D₃ Response Elements (VDRE) in the Parathyroid Hormone (PTH) and Osteocalcin Genes are Different 306
116. Coordinate Regulation of Rat Parathyroid Gland Function by Calcium and 1,25- Dihydroxyvitamin D₃ 308
117. Phosphorylation Pathways Affect Binding of AP-1 and Vitamin D Receptor to their Combined Response Element in the Promoter Region of Human Osteocalcin Gene 310
118. Rapid Actions of Vitamin D Steroids
119. Transmembrane Signal Pathways Induced by Calcitriol, Estradiol, Testosterone and Progesterone in Osteoblasts 315
120. Non-Nuclear Actions of 1a,25(OH)₂D₃ and 24R,25(OH)₂D₃ in Mediating Intestinal Calcium Transport: The Use of Analogs to Study Membrane Receptors for Vitamin D Metabolites and to Determine Receptor Ligand Conformational Preferences 324
121. Nongenomic Effects of Vitamin D 333
122. Binding of the Occupied Vitamin D Receptor (VDR) to Extra-Nuclear Sites: A Potential Mechanism of Nongenomic Actions of 1a,25(OH)₂D₃ 341
123. A Common Mechanism for the Vitamin D Reeeptor Activation and for the Nongenomic Actions of Calcitriol 345
124. The Calciotropic Hormone 1,25(OH)₂-Vitamin D₃ Stimulates Phospholipase D Activity in Cultured Muscle Cells 347
125. Rapid Non-Genomic Effect of 1a,25-Dihydroxyvitamin D₃ on Osteoblast Nuclei 349
126. 1a,25-Dìhydroxyvitamin D₃ Induces a Rapid and Sustained Increase in Cytosolic Calcium in Cultured Human Keratinocytes 351
127. Aged-Related Changes in the Non-Genomic Response of Intestinal Mammalian Cells to 1,25-Dihydroxy-Vitamin D₃ 353
128. Video Imaging of Intracellular Calcium in Insulinoma Cells: Effects of 1,25(OH)₂D₃ 355
129. Cellular Signalling Responses Mediated by 1,25(OH)₂-Vitamin D₃ in Rat and Chick Myoblasts 357
130. Involvement of Adenylate Cyclase System in 1,25-Dihydroxyvitamin D₃ Rapid Stimulation of Ca^{2 +} Uptake by Heart Cells 359
131. Specific Binding of 1,25-Dihydroxyvitamin D₃ to Rat Colonocyte Basolateral Membranes 361
132. Protein Kinase C Participates in the Signal Transduction Pathway Triggered by 1,25-Dihydroxyvitamin D₃ in Myocytes 363
133. Calbindins D—Function and Gene Regulation: Calcium Transport
134. Mechanistic Studies on Intestinal Ca^{2 +} Transport 367
135. Vitamin D, the Intestinal Plasma Membrane Calcium Pump Gene Expression and the Calbindins 376
136. Tissue Specific Calbindin-D_9K Gene Regulation by Calcitriol and Sexual Hormones 385
137. Proteins that Bind to the Calbindin-D_9K Promoter: Known Factors and a New Intestinal Factor 394
138. Studies of the Human Calbindin-D_9K Gene 396
139. Calbindins Revisited in the Rat Dental Pulp 398
140. In Situ Hybridization of Calbindins mRNAs in Rat Ameloblasts 400
141. Immunoreactive Calbindins-D_28K and _9K Mineralization of Rat Epiphyseal Chondrocytes in Culture 402
142. Regulation of Calbindin-D_28K by Parathyroid Hormone in MDBK Cells 404
143. Phosphorylation and Modulation of Calbindin D_28K by Activation of Protein Kinase C (PKC) 406
144. Caco-2 Cells: A Human Intestinal Cell Line for Studying the Biologic Activity of Vitamin D Analogs 408
145. EGF Down Regulates Both Calbindin D_28K and the VDR in MDBK Cells 410
146. Does Calbindin-D_28K Buffer Intracellular Free Calcium? 412
147. Calbindin-D_28K (CaBP-D_28K) in the Rat Endocrine Pancreas: In Vivo and In Vitro Immunolocalization and its Regulation by Vitamin D₃ Deficiency and 1,25- Dihydroxyvitamin D₃ 414
148. Effect of Two Antiestrogens (Tamoxifen and ICI 182780) on Calbindin-D_9K Gene Expression In Vivo in the Rat Uterus, and In Vitro in Primary Cultures of Myometrial Cells 416
149. Identification of a 9 kDa Calcium-Binding Protein in the Chick as Calbindin-D_9K 418
150. Effect of Antisense Sequences Against Calretinin on WiDr Cells 420
151. Intestinal Absorption of Calcium and Strontium Demonstrate a Similar Response to Calcitriol Treatment 422
152. Physiological Concentrations of 24,25(OH)₂ Vitamin D₃ Decrease the Intestinal Calcium Uptake in the Atlantic Cod, Gadus Morhua 424
153. Effects of Vitamin D and DL-Buthionine-S, R-Sulfoximine on Intestinal Calcium Absorption 426
154. 1,25-(OH)₂D₃ Stimulates Ca²⁺ -Uptake Across the Duodenal Brush Border by at Least Two Independent Mechanisms 428
155. Effect of Heavy Metals on the Level of Calbindin D^28K and the Assimilation of Ca in Chick Duodenum 430
156. Apparent Nephron Localization of the 1,25(OH)₂D₃-Stimulated Calmodulin Binding Proteins in the Rat Kidney 432
157. Raised Intestinal Calcium Secretion in the Young Oophorectomised Rat 434
158. Validation of a Simple Test Measuring Intestinal Calcium Absorption Using Strontium as a Marker 436
159. Cell Differentiation
160. In Vitro Effects of Potent Vitamin D₃ Analogs on Proliferation and Differentiation of Seven Human Breast Cancer Cell Lines 441
161. Terminal Differentiation of Human Leukemia Cells (HL60) by a Combination of 1,25-Dihydroxyvitamin D₃ and Retinoic Acid (All Trans or 9-Cis) 449
162. 1,25-Dihydroxyvitamin D₃ Induces Growth of Thyroid C Cells and Inhibits Calcitonin Secretion In Vitro 451
163. Differentiation of Human Myelomonocytic Leukemia Cell Lines by Retinoic Acid and Vitamin D₃ Analogs, MC903 and EB1089: Characterization of Cooperative Effects 453
164. Effect of Ascorbate and Calcitriol on HL-60 Promyelocytic Cell Line Proliferation and Differentiation 455
165. Evidence for a Vitamin D Paracrine System Regulating Fetal Pneumocyte Type II Maturation: Local Synthesis of 1,25-(OH)₂D₃ by Lung Fibroblasts 457
166. Inhibition of IEC-6 Cell Growth by 1,25(OH)₂D₃: Involvement of TGFß 459
167. Interactions between Vitamin D Derivatives, Retinoids and Granulocyte Macrophage - Colony Stimulating Factor in Leukemic Cell Differentiation 461
168. 1,25(OH)₂D₃ and Agents that Increase Intracellular cAMP Synergistically Inhibit the Proliferation of Mouse Fibroblasts 463
169. 1a,25-Dihydroxyvitamin D Rapidly Triggers Inhibition of Fibroblast Contraction of Collagen Lattices 465
170. Cancer 467
171. Immunology 529
172. Dermatology 559
173. Neurosciences 619
174. Renal Osteodystrophy 647
175. Bone and Cartilage 673
176. Miscellaneous Biological Actions of Vitamin D Metabolites and Analogs 735
177. Assays for Vitamin D Steroids 747
178. Nutrition 767
179. Osteoporosis 797
180. Neonatology and Pregnancy 867
181. Gerontology 875
182. Other Basic Science Topics 883
183. Other Clinical Topics 897
184. Author Index 937
185. Subject Index 947
186. Cell Line Index 965
187. Zoo Index 967
188. Backmatter 968