Chemistry and Biology of Pteridines : : Pteridines and Folic Acid Derivatives. Proceedings of the International Symposium on Pteridines and Folic Acid Derivatives, Chemical, Biological and Clinical Aspects. / 8, : Montreal, Canada, June 15–20, 1986 / / ed. by B. A. Cooper, V. M. Whitehead.
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| Other title: | Frontmatter -- Preface -- Acknowledgments -- Contents -- How it all Began: A Brief History of the Pteridine Symposia -- The Gowland Hopkins Lecture: The Mechanisms of Action of Folate and Pterin Requiring Enzymes -- Section A: Chemistry of Pterins and Folates -- Side-Chain Chemistry of Pteridines -- A General Method for the Synthesis of 10-Substituted-10-Deaza Folate Analogues -- Synthesis and Properties of Pyrimidodiazepines as Ring-Strained Probes of Pterin Utilizing Enzymes -- Summary: Pterin and Folate Chemistry -- A Facile Method for Preparing 2,4-Diamino-5,8-Dideazapterins -- Synthesis of 5,10-Dideaza-5,6,7,8-Tetrahydrofolic Acid (DDATHF) and Analogs -- Synthetic Routes to Methotrexate- and Folic Acid-Polyglutamates of High Chemical and Enantiomeric Purity -- In Vivo and In Vitro Evaluations of 5-[4-(Substituted Aryl)-1- Piperazinyl]-6-Alkyl-2,4-Pyrimidinediamines as Antitumor Agents -- The Electrochemical Oxidation of Tetrahydropterin Derivatives -- A Practical Synthesis of (6R)- and (6S)-5,6,7,8-Tetrahydrobiopterins -- Chemical Synthesis and Properties of Quinonoid (6R)-Dihydrobiopterin -- Pyrazine-Ring Conformations of Tetrahydropterins and Quinonoid-Dihydropterins -- Hydrogenation of Silylated Pterins in Benzene Solution -- N(5)-Alkylation of Polyacetylated 5,6,7,8-Tetrahydroneopterins -- Oxidations Photosensitized by Pterins and Diaminopteridines -- Structure of the Riboflavin Synthase/Lumazine Synthase Complex. Arrangement and Chain Folding of Subunits in the Icosahedral Capsid -- Use of C18 Silica Cartridges to Purify and Characterize Pterins -- Synthesis and Structure-Activity Relationships of Tetrahydrobiopterin Cofactor Analogues -- Synthesis, Purification and Properties of a New Class of Pteridine Derivatives -- Summary: Chemistry of Pterins -- Section B: Biosynthesis and Biochemistry of Pterins -- Biosynthesis of Tetrahydrobiopterin and Related Compounds in Drosophila melanogaster -- Tetrahydrobiopterin Biosynthesis in Man -- The Biosynthesis of Tetrahydrobiopterin in the Bovine Adrenal Medulla -- The Biosynthesis of Tetrahydrobiopterin in Rat Brain -- Summary: Biosynthesis of Tetrahydrobiopterin -- The Metabolic Role of Tetrahydrobiopterin -- Spectroscopic Studies on Tyrosine 3-Monooxygenase from Bovine Adrenal Medulla: A Blue Iron Protein -- Queuine-Lacking tNRAs in Relation to the Grade of Malignancy of Specific Tumors, Possible Role of Pteridines -- Pteridine Synthesis During Interaction of Interleukin 2 with T Lymphocytes - Modulator Function in IL-2 Signal Transmission -- Section C: Biology of Pterins -- Dopamine Neurons in Culture: A Model System for Examination of Neuronal Biopterin Metabolism -- Role of the Pituitary in the Regulation of Tetrahydrobiopterin Biosynthesis in the Non-Neuronal Tissues -- Distribution of GTP Cyclohydrolase-I, Neopterin, and Biopterin in the Human Brain -- Enzymatic Synthesis of 6,7-Dimethyl-8-Ribityllumazine -- A Model for Hyperphenylal aninaemia Due to Tetrahydrobiopterin Deficiency -- The Effect of Biopterin and its Reduced Derivatives on Cultured Human Lymphocytes -- Developmental Aspects of Biopterin Metabolism in Human -- Screening for Biopterin Defects Among Hyperphenylalaninemic Patients: Report of a Canadian Program After 3 Years -- Need for Therapy in utero of Fetuses with Tetrahydrobiopterin Deficiency -- Pteridine Metabolism in Patients Suffering from Amyotrophic Lateral Sclerosis -- Urinary Neopterin in Cocaine-Abusing Individuals -- Features of Neopterin Determination in Clinical Use -- Diurnal Variation in Urinary Pterin Excretion in Man -- The Relationship between Pteridines and Colour Dimorphism in the Scorpion Fly -- Pteridine Biosynthesis and Manifestation of Pigment Phenotypes in Normal and Neoplastic Cells of Goldfish in Vitro -- Light Depending Regulations of Pteridines in the Retina -- Differences in the Regulation of Tetrahydrobiopterin Biosynthesis in Neuronal Cells in Culture -- NADPH- and NADH-Specific Dihydropteridine Reductase in Teratocarcinoma Cells in Culture: Effect of Nerve Growth Factor Treatment of the Cells on the Enzyme Activities -- Reversibility of α-Diketo Reductase Activity by Sepiapterin Reductase -- Non-Enzymatic Synthesis of "Drosopterins" from Dihydropterin and 2-Amino-4-0xo-6-Acetyl-3H, 9H-7,8-Dihydropyrimido [4,5b] [1,4]Diazepine -- BH4 Biosynthesis: 1H-NMR Evidence for the Pyruvoyl-Tetrahydropterin-Synthase Catalyzed Formation of 6-Pyruvoyl-Tetrahydropterin from Dihydroneopterin Triphosphate -- Catabolism of Tetrahydrobiopterin in Man -- Pteridine Biosynthesis in Human Amniocytes and Chorionic Villi -- The Role of the Kidney in Biopterin Metabolism -- Tetrahydrobiopterin-Producing Enzyme Activities in Liver of Animals and Man -- Effect of 3-Hydroxykynurenine on GTP Cyclohydrolase Activity and on the Pteridine Pattern in Drosophila melanogaster -- Tetrahydrobiopterin Metabolism in Normal Brain, Senile Dementia of the Alzheimer Type and Down's Syndrome -- Summary: Biology of Pteridines -- Biosynthesis of Pteridines and Metabolism of Aromatic Amino Acids in Drosophila melanogaster -- The Inhibition of tRNA Transglycosylases by Pteridines as a Mean for Metabolic Control of Gene Expression -- Modulation of Dopamine Synthesis by Nerve Terminal Autoreceptors: A Role for Tetrahydrobiopterin? -- A Monoclonal Antibody Reacting with All Three Aromatic Amino Acid Hydroxylases -- Alterations in Cofactor-Dependent Activity of Phenylalanine Hydroxylase as a Function of pH -- Interaction of a Monoclonal Antibody with Rat Liver Phenylalanine Hydroxylase -- The Effect of Dietary Iron on the Activity of Rat Liver Phenylalanine Hydroxylase -- Strict Requirement of Fe2+ for Tryptophan 5-Monooxygenase from Mouse Mastocytoma, P-815 -- Tetrahydrobiopterin and the Regulation of Catecholamine Synthesis in Bovine Adrenal Medullary Chromaffin Cells -- Cofactor Activity of Tetrahydropterins for Tyrosine Hydroxylation in PC12 Pheochromocytoma Cells -- Summary: Pterin-Dependent Biological Reactions -- Tetrahydrobiopterin Deficiency. Analysis from an International Survey -- Cofactor Specificity of 6,6-Disubstituted Tetrahydropterins, and their Potential in the Treatment of Neurological Disorders -- Normal Concentrations of Tetrahydrobiopterin in the Cerebrospinal Fluid of Patients with Dihydropteridine Reductase Deficiency -- Prenatal Diagnosis of Tetrahydrobiopterin Deficiency -- Defective Biopterin Biosynthesis in a Chinese Infant -- Correlation of Dihydropterine Reductase Cross Reacting Material with Non-Responsiveness to a Tetrahydrobiopterin Load -- Neopterin and Dihydroneopterins in Serum of Controls and Patients with Various Diseases. Circadian Rhythm of Neopterin. Influence of Cortisol? -- Neopterin Content and GTP-Cyclohydrolase Activity of Blood Cells of Controls and Patients Positive for LAV/HTLV-III Antibodies -- Neopterin in Bone Marrow Transplant Monitoring: An Improvement in its Use for GVHD Diagnosis -- Importance of Neopterin Determination in Individuals at Risk for AIDS -- Biochemical Aspects of Pteridines During Interaction Between Activated T-Lymphocytes and Monocytes/Macrophages in Patients -- Summary: Pterins and Human Illness -- Section D: Folates and Pterins in Mammalian Tissues -- Folates in Tissues and Cells. Support for a "Two-Tier" Hypothesis of Regulation of One-Carbon Metabolism -- Elevation in the Rate of Cellular Folate Catabolism in Mid-Pregnancy in the Rat -- The Red Blood Cell as a Storage Site for Folic Acid -- Methotrexate and Biopterin Levels in Blood Following Low Dose Administration for Psoriasis -- Summary: Folates in Tissue and Cells -- Folate Rescue of N2O-Induced Inhibition in Murine Lymphocytes -- Folate Absorption and Metabolism in Alcohol Fed Rats -- Chronic and Acute Effects of Ethanol on Renal Clearance and Urinary Excretion of Folate in Rats -- Effect of Chronic Anticonvulsant Treatment on Folate Concentrations in the Rat -- Alcohol Induced Methyl Group Wastage as a Possible Cause of Fatty Liver -- Folate Catabolism in the Syrian Golden Hamster -- The Level of Folate Catabolism in Normal Human Populations, Suggesting that the Current Level of RDA for Folate is Excessive -- Microdetermination of Folate Monoglutamates in Serum by High-Performance Liquid Chromatography with Electrochemical Detection -- Folate Status in Psychiatric Patients: Relationship with CSF Neurotransmitter Metabolites -- Folate, Thiamine and Vitamin B12 Levels in Outpatient Epileptics -- Effect of Aspirin Ingestion on Folate Bioavailability Evaluated by Rat Liver Bioassay -- Brush Border Pteroylpolyglutamate Hydrolase in Pig Jejunum -- Use of CI-920 in the Characterization of the Methotrexate Transport Defect in a Resistant Human Leukemic CCRF-CEM Cell Line -- The Effect of Oxidative Stress on Methotrexate (MTX) Transport by Rat Hepatocytes -- Folate Transport by Pig Intestinal Brush Border Vesicles -- Depressed Folate Transfer Across the Mammary Gland Secondary to Iron Deficiency in the Rat -- Studies on the Mechanism of Folate Transport in Isolated Hepatocytes -- Analysis of the pH and Na+ Dependence of Intestinal Folate Transport -- Intestinal Transport of Folate. Characterization of the Transport Events at the Brush Border and the Basolateral Membranes -- The Synthesis of Some Novel Probes of Folate Transport and Binding -- Photoaffinity Probes of Dihydrofolate Reductase and of the Membrane Carrier for Folate Analogues -- The Use of Biosynthetic Radioactive Folylpolyglutamates to Study Intestinal Digestion and Absorption of Folate -- Selective Inhibition of Bacterial Carboxypeptidase G and Pancreatic Conjugase by 2-Mercaptomethylglutaric Acid -- Summary: Folate Absorption and Transport -- Studies on Glycine-N-Methyltransferase -- Folate Binding Protein from Pediococcus Cerevisiae Strains Possessing Active Transport Systems for Folates -- Immobilized Folate Binding Protein from Cow's Milk Used for Quantitation of Folate -- Characterization of Rabbit Antibodies Against the Folate Binding Protein from Cow's Milk -- Section E: Enzymology of Folates -- 1. Thymidylate Synthase -- Genetic and Chemical Studies on Thymidylate Synthase -- Active Site Probes of Thymidylate Synthetase -- Resonance-Raman Spectroscopic Identification of the Transient Intermediates Formed in the Native Ternary Complex with Thymidylate Synthase -- The Reversal of the Cytotoxicity of Folate-Based Thymidylate Synthase Inhibitors in Cultures L1210 Cells -- Thymidylate Synthase Activity in the Tapeworm, Hymenolepis diminuta -- Identification of Poly G Bound to Thymidylate Synthase -- Methotrexate Derivates of Deoxyuridylate Showing Inhibitory Properties for Thymidylate Synthetase from Lactobacillus casei -- Comparison of Thymidylate Synthase Isolated from Mouse Normal and Tumour Tissues -- Thymidylate Synthase Interaction with Analogues of dUMP and 5-Fluorid- 2'-Deoxyuridine-5'-Phosphate with Modified Phosphate Groups -- An In Vitro System for Studies on Inhibition of the Thymidylate Cycle -- N10-Propargyl-5,8-Dideazafolic Acid Polyglutamates as Inhibitors of Thymidylate Synthase and their Intracellular Formation -- Sequential CMF in Metastatic Breast Cancer: An Attempt to Increase Effectiveness by Means of Biochemical Modulation -- Model Studies of Thymidylate Synthase Reaction -- Synergistic Interaction Between Folinic Acid and the Fluoropyrimidines -- 2. Methionine Biosynthesis -- Methionine Biosynthesis -- Impaired Formylation and Uptake of Tetrahydrofolate by Rat Small Gut Following Cobalamin Inactivation -- Heterogeneity in Functional Methionine Synthase Deficiency -- Summary: Methionine Biosynthesis -- 3. Folyl Polyglutamate Synthetase -- Folylpoly-γ-glutamate Synthetase -- Cytotoxic Effects and Inhibition of Folylpolyglutamate Synthetase by Folate Analogs Containing 2, Omega-Diaminoalkanoic Acids -- An Upstream Gene Regulates the Expression of Folylpolyglutamate Synthetase-Dihydrofolate Synthetase in Escherichia coli -- Occurence and Synthesis of Pteroyl-γ-glutamyl-γ-glutamyl-poly-α-glutamates in Escherichia coli -- Summary: Folylpolyglutamate Synthesis -- The Metabolism of Pteroylpolyglutamates -- Dihydropteroyl Hexaglutamate and T4 Phage Baseplate Assembly -- Effects of Polyglutamylation on Folate Cofactor and Antifolate Activity in the Thymidylate Synthase Cycle of Permeabilized Murine Leukemia L1210 Cells -- Summary: Pteroylpolyglutamate metabolism -- 4. Dihydrofolate Reductase -- Recent Advances in the Study of Dihydrofolate Reductase -- The 2.8 Å Structure of a Type II Plasmid Encoded Dihydrofolate Reductase -- Mutations in the Human Dihydrofolate Reductase -- Theoretical Studies of the Structure, Conformational and Electronic Properties of Anticancer Folate Inhibitors -- Binding of Inhibitors with Spin-Labeled Side Chains to Dihydrofolate Reductase (DHFR) from Several Species -- Affinity Labeling of Dihydrofolate Reductase with an Iodoacetyl Lysine Analogue of Methotrexate -- Escherichia coli Dihydrofolate Reductase Isolated as a Folate Complex -- Dihydrofolate Reductase from Soybean Seedlings -- Use of Antibodies as Structural Probes of Dihydrofolate Reductases and Enzyme-Ligand Complexes -- Cooperativity in Inhibitor Binding to Neisseria gonorrhoeae Dihydrofolate Reductase -- pH Studies of the Reaction Catalyzed by Dihydrofolate Reductase from E. coli -- Effects of pH on Reactions Catalyzed by Dihydrofolate Reductase from Chicken Liver -- Unconjugated Dihydropterin Substrates for Bovine Liver Dihydrofolate Reductase -- Enzymatic Characterization of Recombinant Human Dihydrofolate Reductase Produced in E. coli -- Levels of Folates and Methotrexate Polyglutamate Formation in Chinese Hamster Ovary Cells Lacking Dihydrofolate Reductase -- Methotrexate in Adjuvant Arthritis -- Computer Graphic Modeling in Drug Design: Conformational Analysis and Active-Site Modeling of Lipophilic Diaminopyrimidines -- Effect of Antifolates 10-Methyl- and 10-Ethyl-10-Deaza-Aminopterin on a Human Breast Cancer Cell Line -- Biochemical and Cytotoxic Effects of the Erythro- and Threo-Isomers of Gamma-Fluoro-Methotrexate -- 5. Other Folate Enzymes -- C1-Tetrahydrofolate-Synthase, a Multifunctional Enzyme Involved in Purine Metabolism, and its Related Monofunctional Enzymes -- The Interaction of Tetrahydropteroylpolyglutamates with 10-Formyltetra-Hydrofolate Synthetase -- Summary: Folates in C 1 Metabolism -- Chemical Aspects of Dimethylglycine Dehydrogenase and Sarcosine Dehydrogenase -- Folate Normalizes Elevated PRPP Levels of Folate-Deficient HL-60 Cells -- Stereochemistry of Hydride Transfer to NADP+ by Methylene Tetrahydrofolate Dehydrogenase from Pig Liver -- The Effects of Thyroxine Status on Hepatic Levels of 10-Formyltetrahydrofolic Acid: NADP Oxidoreductase -- Interaction of Homocysteine with Methionine Synthetase -- Minor Form of Human Hepatic Betaine: Homocysteine S-Methyltransferase -- Studies of Cobalamin-Dependent Methionine Synthase from Escherichia coli B -- Inhibition of Methylenetetrahydrofolate Reductase by Adenosyl Methionine -- Regulation of Folate Homeostasis -- An Endogenous Inhibitor of Neurospora Folylpolyglutamate Synthetase -- Folylpolyglutamate Hydrolase from Beef Liver -- Use of Mammalian Cell Transformation to Isolate Genomic Sequences Encoding Human Folylpolyglutamate Synthetase (FPGS) and Dihydrofolate Reductase (DHFR) -- Section F: Methotrexate and Other Anti-Folates -- Antifolates: Expanding Horizons in 1986 -- Deaza Derivatives of Tetrahydrofolic Acid. A New Class of Folate Antimetabolite -- Structure Activity Relationships of Novel Triazine Antifolates -- The Effect of 7-Hydroxymethotrexate on the Antitumor Activity and Host Toxicity of Methotrexate In Vivo -- Summary: The Biology of Antifolates -- Crystal Structure of Methotrexate and its Conformational Comparison with Related Structures -- Effect of Methotrexate on Reduced Folates and Thymidylate Synthesis During Growth of L1210 Cells -- Dihydrofolate Reductase from Human Osteosarcoma Cells Resistant to Methotrexate -- Evidence for Direct Inhibition of Metabolic Pathways as a Mechanism of Action of Methotrexate -- Inhibition of Dihydrofolate Reductase and Thymidylate Synthase by Methotrexate Polyglutamate Analogues Lacking "Internal" α-Carboxyl Groups -- The Antifolate Activity of Poly-γ-Glutamyl Derivatives of Methotrexate, 10-Deazaaminopterin and 10-Ethyl-10 Deazaaminopterin -- Polyglutamation of the Thymidylate Synthase Inhibitor, N10-Propargyl-5,8-Dideazafolic Acid (CB 3717), in Organs of Ehrlich Ascites Carcinoma-Bearing Mice -- 5,8-Dideazafolates as Substrates for Folypoly-γ-Glutamate Synthetase from Pig Liver -- 5-Substituted-5-Deaza Analogues of Classical Antifolates -- Azido-Substituted Antifolate Drugs: Synthesis, Structure, and Activity -- Summary: Novel Antifolates -- Author Index -- Subject Index -- List of Participants -- Backmatter |
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| Format: | Mode of access: Internet via World Wide Web. |
| ISBN: | 9783110856262 9783110637342 |
| DOI: | 10.1515/9783110856262 |
| Access: | restricted access |
| Hierarchical level: | Monograph |
| Statement of Responsibility: | ed. by B. A. Cooper, V. M. Whitehead. |
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