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Retinoids
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Section A: Metabolism, Pharmocokinetics and Action of Retinoids.- 1 Physical-Chemical Properties and Action of Retinoids.- A. Introduction.- B. Behavior of Retinoids in an Aqueous Environment.- I. Aqueous Solubility.- II. Self-Association of Retinoids in Water.- III. Lability of Retinoids in Water.- C. Interactions of Retinoids with Membranes.- I. Effects of Membrane Lipid Composition on Membrane- Retinoid Interactions.- II. Effects of the Radius of Curvature of Membranes on Membrane-Retinoid Interactions.- III. Ionization Behavior of Retinoic Acid in Membranes.- D. Interactions of Retinoids with Proteins.- I. Binding Affinities.- 1. Ligand Binding Affinities of Retinoid-Binding Proteins.- 2. Ligand Binding Affinities of Retinoid Nuclear Receptors.- II. Kinetics of the Interactions of Retinoids with Proteins.- 1. Rates of Dissociation of Retinoids from Retinoid- Binding Proteins.- E. Some Implications for Retinoid Transport Processes.- I. Uptake of Retinol by Target Cells.- II. Targeting of Retinoids by IRBP.- F. Concluding Remarks.- References.- 2 Biosynthesis, Absorption, Metabolism and Transport of Retinoids.- A. Introduction.- B. Intestinal Absorption of Retinol and Biosynthesis of Retinol from Carotenoids.- I. Uptake and Luminal Metabolism of Dietary Preformed Vitamin A (Retinyl Esters, Retinol, and Retinoic Acid).- II. Uptake and Metabolism of Dietary Provitamin A Carotenoids.- III. Intramucosal Metabolism.- 1. Retinoic Acid Formation from Retinal Derived from Carotenoids.- 2. Role of Cellular-Retinol Binding Protein, Type II.- 3. Retinol Esterification and the Packaging of Dietary Retinoid into Chylomicrons.- C. Circulating Chylomicrons and Chylomicron Remnant Formation.- I. Hepatic Clearance of Chylomicron Remnants.- II. Extrahepatic Tissues and Chylomicron Remnant Retinoid.- D. Retinoid Processing and Metabolism within the Liver.- I. Uptake and Processing of the Chylomicron Remnant Retinyl Ester by Hepatocytes.- II. Retinoid Metabolism and Storage in the Hepatocyte.- 1. Cellular Retinol-Binding Protein, Type I.- 2. Hepatic LRAT Activity.- III. Retinoid Transfer Between Hepatocytes and Stellate Cells.- IV. Retinoid Metabolism and Storage in Hepatic Stellate Cells.- E. Extrahepatic Processing and Metabolism of Retinol and Retinyl Ester.- F. Retinoid Delivery to Target Tissues.- I. Retinol Bound to RBP.- 1. Cellular Synthesis and Secretion of Retinol-RBP and Its Regulation.- 2. The RBP Gene and Its Regulation.- 3. Structural and Physiochemical Properties of RBP, TTR, and the RBP-TTR Complex.- 4. Retinol-RBP Turnover from the Circulation.- 5. RBP Receptor.- II. Plasma all-trans-Retinoic Acid.- III. Plasma 13-cis-Retinoic Acid.- IV. Lipoprotein Bound Retinyl Ester.- V. Glucuronides of Retinol and Retinoic Acid.- VI. Retro-Metabolites of Retinol.- G. Summary.- References.- 3 Retro-Retinoids: Metabolism and Action.- A. Introduction.- B. Vitamin A and the Immune System.- C. General Properties of Retro-Retinoids.- D. Cellular Effects of Retro-Retinoids.- I. Growth of B Lymphocytes.- II. Activation of T Lymphocytes.- III Activation of Fibroblasts.- IV. Cell Growth vs. Cell Differentiation: Retinol Metabolism in HL-60 Cells.- V. Intracellular Signaling.- 1. Anhydroretinol-Induced Cell Death.- 2. Evidence for a Transmembrane or Cytoplasmic Receptor.- E. Retro-Retinoid Metabolism.- I. 14-Hydroxy-Retro-Retinol.- II. 13,14-Dihydroxy-Retinol.- III. Biosynthesis of Anhydroretinol.- F. Conclusion.- References.- 4 Retinoic Acid Synthesis and Metabolism.- A. Introduction.- B. Cellular and Extracellular Retinoid Binding Proteins.- I. Cellular Retinol Binding Proteins.- II. Cellular Retinoic Acid Binding Proteins.- III. Other Retinoic Acid Binding Proteins.- C. Retinoic Acid Synthesis.- I. Oxidation of Retinol.- 1. Role of Cytosolic Dehydrogenases.- 2. Role of Microsomal Dehydrogenases.- II. Oxidation of Retinal.- III. Formation of 9-cis-Retinoic Acid.- IV. Direct Synthesis of Retinoic Acid from Carotenoids.- D. Oxidative Metabolism of Retinoic Acid.- I. Role of the Cytochrome P450 System in Retinoic Acid Oxidation.- II. Other Metabolism of Retinoic Acid.- E. Summary and Future Needs.- References.- Section B: Binding Proteins and Nuclear Receptors.- 5 Nuclear Retinoid Receptors and Mechanisms of Action.- A. Introduction.- B. The Nuclear Retinoid Receptors and Their Cousins.- C. The RAREs: Further Specification of the Ligand Response.- D. Interaction of Retinoid Receptors with Coactivators, Corepressors, and Basal Transcription Factors.- E. Differentiation-Proliferation Switches: Interaction with Other Signal Transducers.- F. CBP/p300, a Cointegrator of Multiple Signaling Pathways.- G. A Role for Histone Acetylation in Receptor-Mediated Transactivation?.- H. Apoptosis Induction by Special Retinoids: A Novel Pathway?.- I. Future Prospects.- References.- 6 RAR-Selective Ligands: Receptor Subtype and Function Selectivity.- A. Introduction.- B. Structural Differences Between RAR-Selective and RXR-Selective Ligands.- I. The Effect of Bridging Groups on Conformationally Restricted Retinoids.- II. The ?-Methyl Effect.- III. 9-Cis-Locked vs 9-Trans-Locked Retinoids.- C. RAR Subtype Selective Agonists.- I. RAR? Selective Agonists.- II. RAR? Selective Agonists.- III. RAR?Selective Agonists.- D. RAR Antagonists, Neutral Antagonists, and Inverse Agonists.- I. RAR Antagonists.- II. RAR Inverse Agonists and Neutral Antagonists.- E. Pharmacology of RAR Selective Agonists and Antagonists.- I. RAR? Selective Agonists.- II. RAR? Selective Agonists.- III. RAR?Selective Agonists.- IV. RAR Antagonists and Inverse Agonists.- References.- 7 RXR-Speeific Agonists and Modulators: A New Retinoid Pharmacology.- A. Introduction.- B. Ligand-Dependent Activation of Transcription By RXR.- I. Activation of Permissive Heterodimers.- II. RXR Agonists Activate RXR-RAR Heterodimers When The RAR Binding Pocket Is Occupied.- III. The Phantom Ligand Effect.- C. RXR Pharmacology.- I. Sensitization of Diabetic Mice to Insulin by RXR Agonists.- II. Chemoprevention/Chemotherapy of Carcinogen-Induced Breast Cancer.- D. Conclusions and Future Directions.- References.- Section C: Differentiation, Proliferation, and Cancer.- 8 Growth Control by Retinoids: Regulation of Cell Cycle Progression and Apoptosis.- A. Introduction.- B. Mechanisms of Retinoid Action.- I. Retinoid Receptor-Dependent Mechanisms.- II. Retinoid Receptor-Mediated Control of Cell Proliferation.- III. Receptor-Independent Regulation of Cell Proliferation.- C. Control of Cell Cycle Progression by Retinoids.- I. Overview of Cell Cycle Regulation.- II. Cell Cycle Regulatory Targets of Retinoid Action.- 1. Retinoids Can Affect the Rb Pathway at Several Levels.- 2. Regulation of c-myc Expression.- 3. Modulation of AP-1-Mediated Growth Signals.- 4. Effects on Miscellaneous Cell Cycle Proteins.- D. Regulation of Apoptosis.- I. Apoptotic Mechanisms.- II. Regulation of Apoptosis by Retinoids.- 1. Receptor-Mediated Induction of Apoptosis.- 2. Receptor-Mediated Inhibition of Apoptosis.- 3. Retinoid Receptor Independent Mechanisms.- a) Mechanisms of 4-HPR Action in Apoptosis.- b) Mechanisms of AHPN Action.- E. Summary.- References.- 9 Retinoids and Differentiation of Normal and Malignant Hematopoietic Cells.- A. Introduction.- B. Retinoids and Hematopoiesis.- I. Effect of Retinoic Acid on Cellular Proliferation, Differentiation, and Apoptosis of Hematopoietic Leukemic Cells.- 1. Effect on Myeloid Leukemic Cell Differentiation.- 2. Effect on Acute Promyelocytic Leukemic Cells.- 3. Effect on Induced Myeloid Leukemic Cell Apoptosis.- II. Retinoic Acid as a Novel Myeloid Differentiation Factor.- III. Retinoic Acid Control of Myeloproliferative Growth.- C. Retinoic Acid Signaling Pathways in Hematopoietic Cells.- I. Differential Expression of Nuclear Retinoic Acid Receptors and Retinoid-Binding Proteins.- II. Alteration of RARa in Hematopoietic Malignancies.- 1. Molecular Characteristics of APL.- 2. Alterations of RARa in Other Malignancies.- D. Retinoic Acid as a Therapeutic Agent in Hematopoietic Malignancies.- I. Acute Promyelocytic Leukemia.- 1. Retinoid Resistance in APL.- 2. Retinoic Acid Syndrome and Other Side Effects of RA Therapy.- 3. Mechanisms of retinoic acid induced differentiation in APL patients.- II. Retinoids as Therapeutic Alternative to Myeloproliferative Disorders.- E. Summary and Perspectives.- References.- 10 The Retinoids: Cancer Therapy and Prevention Mechanisms.- I. Summary.- II. Mechanisms of Retinoid Action.- IV. Retinoids and Cancer Chemoprevention.- V. In Vitro Models for Retinoid Activity in Cancer Therapy and Prevention.- A. The Multipotent NT2/D1 Human Embryonal Carcinoma Line.- B. Acute Promyelocytic Leukemia In Vitro Models.- C. An In Vitro Lung Cancer Prevention Model.- VI. Summary and Future Directions.- References.- 11 Aberrant Expression and Function of Retinoid Receptors in Cancer.- A. Introduction.- B. Aberrant nuclear retinoid receptor expression and function in cultured cancer cell lines.- I. Expression of Nuclear Retinoid Receptors in Lung Cancer Cell Lines.- II. Expression of Nuclear Retinoid Receptors in Head and Neck Squamous Cell Carcinoma Cell Lines.- III. Expression of Nuclear Retinoid Receptors in Esophageal Cancer Cell Lines.- IV. Expression of Nuclear Retinoid Receptors in Breast Cancer Cell Lines.- V. Expression of Nuclear Retinoid Receptors in Normal Skin and Skin Cancer Cell Lines.- VI. Expression of Nuclear Retinoid Receptors in Cervical Cancer Cell Lines.- VII. Expression of Nuclear Retinoic Acid Receptors in Embryonal Carcinoma Cell Lines.- VIII. Expression of Nuclear Retinoid Receptors in Myeloid Leukemia.- C. Aberrant Nuclear Retinoid Receptor Expression in Specimens from Normal, Premalignant, and Malignant Tissues.- I. Expression of Aberrant RAR? in Acute Promyelocytic Leukemia.- II. Expression of Nuclear Retinoid Receptors in Adjacent Tissues and Head and Neck Squamous Cell Carcinoma.- III. Expression of Nuclear Retinoic Acid Receptors in Hamster Cheek-Pouch Mucosa During 7,12-Dimethylbenz[a]anthracene-Induced Carcinogenesis.- IV. Expression of Nuclear Retinoid Receptors in Adjacent Bronchial Epithelium and Non-small Cell Lung Cancer.- V. Expression of Nuclear Retinoid Receptors in Adjacent Normal, Premalignant, and Malignant Breast Tissues.- VI. Expression of Nuclear Retinoid Receptors in Normal Skin and Skin Cancers.- VII. Expression of the Nuclear Retinoid Receptors in Normal Uterine Cervix and Cervical Cancer.- D. Mechanisms of Altered Receptor Expression and Function In Vitro and In Vivo.- References.- Section D: Development and Teratogenesis.- 12 Genetic and Molecular Approaches to Understanding the Role of Retinoids in Mammalian Spermatogenesis.- A. Introduction.- I. Historical Perspective of the Role of Vitamin A in Spermatogenesis.- II. Focus of This Review.- B. Serum and Cellular Retinoid Binding Proteins.- I. Sites of Synthesis and Action.- 1. Retinol Binding Protein and Transthyretin.- 2. Cellular Retinol and Retinoic Acid Binding Proteins.- II. Potential Functions During Spermatogenesis.- C. Receptors.- I. Retinoic Acid and Retinoid X Receptors and Their Ligands.- II. Regulation of Transcription by Ligand-Activated Retinoid Receptors.- III. RAR and RXR Expression in the Testis.- D. The Vitamin A Deficient Testis.- E. Genetic Analysis of Retinoid Function.- I. Overview of Mouse Mutants.- II. Mutations in Retinoid Receptors and Binding Proteins with no Testicular Phenotype.- III. Mutations in Retinoid Receptors that Result in Male Sterility.- 1. RARs.- 2. RXRs.- F. Where Do We Go From Here?.- I. Assessment of Lineage Specificity of Receptor Function in the Testis.- II. Identification of In Vivo Cofactors.- III. Potential Targets of Retinoid Action During Spermatogenesis.- 1. Mutations Affecting Spermatogenesis.- 2. Genes Whose Testicular Expression Is Affected by Retinoids.- 3. Other Retinoid-Responsive Genes.- References.- 13 The Role of Retinoids in Vertebrate Limb Morphogenesis: Integration of Retinoid- and Cytokine-Mediated Signal Transduction.- A. Introduction.- B. An Overview of Retinoid Signal Transduction in the Vertebrate Embryo.- I. Retinoid Requirement in Development.- II. Retinoic Acid Synthesizing Enzymes and Degrading Enzymes in Embryos.- III. RARs and RXRs Mediate Retinoic Acid Signal Transduction In Vivo and Are Required for Development.- IV. Retinoid Target Genes.- C. Retinoids in Vertebrate Limb Development.- I. Embryology of the Vertebrate Limb.- II. The Zone of Polarizing Activity.- III. Retinoids and the Generation of the ZPA.- IV. Retinoids in Limb Differentiation.- D. Retinoids in Limb Regeneration.- References.- 14 Retinoids in Neural Development.- A. The Induction of Neuronal Differentiation in Culture.- I. Embryonal Carcinoma Cells and Neuroblastoma Cells.- II. Dissociated or Explanted Neuronal Cells.- III. Neural Crest Cells.- B. The Effects of Excess Retinoids on the CNS.- I. Effect 1: Posteriorisation.- II. Effect 2: Loss of Anterior Hindbrain.- III. Effect 3: Transformation of Anterior Hindbrain.- C. The Effects of RA on Associated CNS Structures.- D. The Effects of a Deficiency of Retinoids on the CNS.- I. Deprivation of Retinoids.- II. Inhibition of RA Synthesis.- E. Endogenous RA in the CNS.- I. HPLC Data.- II. Transgenic Embryos.- III. Reporter Cells.- IV. RA Synthesising Enzymes.- V. Which Cells in the Nervous System Synthesise RA?.- E Binding Proteins and Receptors in the Developing CNS.- I. CRBP I.- II. CRABPI.- III. CRABP II.- IV. RARs and RXRs.- V. Knockouts of Binding Proteins and Receptors.- VI. Disruption of Function.- VII. Receptor Selective Agonists.- G. Conclusions.- References.- 15 Avian Embryo as Model for Retinoid Function in Early Development.- A. Introduction.- B. Teratogenic Effects of Vitamin A Deficiency and Excess.- C. Mammalian Models.- D. Avian Embryo "Retinoid Ligand Knockout " Model.- E. Cardiogenesis.- F. Left-Right Asymmetry.- G. Vasculogenesis.- H. Central Nervous System.- I. Ethanol-Induced Retinoid Depletion.- J. Retinoid Metabolism.- K. Future Directions.- References.- 16 Retinoid Receptors, Their Ligands, and Teratogenesis: Synergy and Specificity of Effects.- A. Introduction.- B. Ligands of the Retinoid Receptors.- I. Endogenous Ligands of the Retinoid Receptors.- II. Retinoid Receptor Ligands in the Embryo.- C. Retinoid Receptors and Binding Proteins in the Embryo.- I. Retinoid Binding Proteins in the Embryo.- II. Retinoid Receptors in the Embryo.- D. Experimental Models for the Study of the Significance of Retinoid Receptors in Teratogenesis.- I. "Loss of Function " Approach: Studies with Null Mutant Mice.- II. "Gain of Function " Approach: Administration of Selective Retinoid Receptor Ligands.- E. Synergistic Teratogenic Action Following Combined Administration of RAR and RXR Ligands.- F. Molecular Pathways of Vitamin A and Retinoid Teratogenesis.- G. Conclusions.- References.- Section E: Skin.- 17 Vitamin A Homeostasis in Human Epidermis: Native Retinoid Composition and Metabolism.- A. Introduction.- B. Total Vitamin A Content of the Epidermis.- C. Vitamin A Metabolites in the Epidermis.- D. Retinoid Composition of Epidermal Compartments.- E. Retinoid Composition of Cultured Human Keratinocytes.- F. Extracellular Retinoid Transport.- I. Retinol.- II. Retinoic Acid.- G. Retinoid Metabolism in Epidermis.- I. Retinoid-Binding Proteins.- 1. Cellular Retinol-Binding Protein.- 2. Cellular Retinoic Acid Binding Proteins.- II. Vitamin A Storage, Retinyl Ester Synthesis and Hydrolysis.- III. Retinoic Acid Synthesis.- IV. Retinoic Acid Metabolism.- V. 3,4-Didehydroretinol Synthesis and Metabolism.- H. Summary and Working Model for Retinoid Metabolism in Epidermis.- I. Future Prospects.- References.- 18 New Concepts for Delivery of Topical Retinoid Activity to Human Skin.- A. Introduction.- B. The "Proligand-Nonligand " Concept.- C. All-trans-Retinol.- D. All-trans-Retinyl Esters.- E. All-trans-Retinal.- F. All-trans-Retinoyl-?-Glucuronide.- G. Conclusions and Perspectives.- References.- 19 Retinoid Receptor-Selective Agonists and Their Action in Skin.- A. The Molecular Aspects of Retinoid Signaling.- I. The Role of Retinoid Receptors.- II. RAR Receptor-Selective Retinoids.- III. RXR Receptor Selective Retinoids.- B. Vitamin A and the Skin.- I. Proliferation and Differentiation Within the Epidermis.- II. Vitamin A and the Skin: The Historical Aspects.- III. RARs and RXRs and the Development of the Skin.- IV. Retinoid Effects upon Keratinocyte Proliferation and Differentiation.- V. Modulation of Inflammation and the Immune Response in Skin by RA.- VI. Retinoid Receptors and Skin Function.- VII. The Development of Synthetic Retinoids and Their Action in Skin.- 1. Adapalene (CD271).- 2. Tazarotene (AGN 190168).- C. Apoptosis: An Emerging Role for Retinoids.- D. Future Prospects.- References.- Section F: Special Effects.- 20 Retinoids in Mammalian Vision.- A. Introduction.- I. Overview of the Visual Process.- II. Anatomy.- III. Nourishment of the Outer Retina.- IV. Overview of the Visual Cycle.- B. Structure and Function of Visual Pigments.- I. Interaction of 11-cis-Retinal and Opsin.- II. Cone Visual Pigments.- III. Identification of the Activated Photoproducts.- C. Visual Pigment Regeneration.- I. All-trans-Retinol Dehydrogenase.- II. Movement of Retinoids Between RPE and Photoreceptors.- III. Regeneration in Rods Compared to Cones.- IV Muller Cells.- V. Control of the Visual Cycle.- VI. Communication Between Neural Retina and RPE.- D. Cellular and Extracellular Retinoid-Binding Proteins.- I. Cellular Retinal-Binding Protein.- II. Interphotoreceptor Retinoid-Binding Protein.- III. Cellular Retinol-Binding Protein.- IV. Retinol-Binding Protein.- E. Diseases Associated with Retinoid Metabolism or Function in the Retina.- I. Congenital Stationary Night Blindness.- II. Autosomal Recessive Retinitis Pigmentosa.- III. Retinoids and Lipofuscin.- F. Summary.- References.- 21 Retinoids and Immunity.- A. Introduction.- B. Innate Immunity.- I. Natural Killer Cells.- II. Phagocytic Cells.- C. Adaptive Immunity.- I. Antibody-Mediated Immunity.- II. Cell-Mediated Immunity.- D. Immunity to Infections.- I. Measles Infection.- II. Human Immunodeficiency Virus Type 1 Infection.- III. Parasitic Infections.- E. Autoimmunity.- I. Rheumatoid Arthritis.- II. Multiple Sclerosis.- F. Lymphocyte Turnover.- G. Vitamin A Metabolism.- I. Active Metabolites for Immune Function.- II. Metabolism During Infection or Inflammation.- H. Mechanisms of Vitamin A Action in the Immune System.- I. Summary and Future Research Directions.- References.

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