Chemistry and Biology of Pteridines and Folates

Table of Contents

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   Book Overview
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   Chapter 1 Natural Pteridines -A Chemical Hobby
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   Chapter 2 Properties and Reactions of Pteridines Carrying Functionalised Side Chains at the 3-Position
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   Chapter 3 N 2 -( N , N -Dimethylaminomethylene)- O 4 -(2- p -Nitrophenyl. Ethyl)-Biopterin: A Versatile Intermediate for a Glycosidation Reaction
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   Chapter 4 The Synthesis of Fluorine-Containing Pterins
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   Chapter 5 Formation of Fe III or Fe II Complexes with Acetylaceto-Nate and 5,6,7,8-Tetrahydropterin as Ligands and Their Activation of Oxygen
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   Chapter 6 Stereoelectronic Effects in the Autoxidative Destruction of Reduced Folate Derivatives
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   Chapter 7 Mindo/3 Molecular-Orbital Calculations on the 6R-BH4 Molecule and Its Metabolic Precursors : Conformation and Activity
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   Chapter 8 Identification, Stereoconfiguration, Chromatographic and Fluorescence Properties of Natural Pterins
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    Chapter 9 The Mechanism of Cofactor Regeneration During Phenylalanine Hydroxylation
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    Chapter 10 Structure Function Studies of the Phenylalanine Hydroxylase Active Site and a Summary of Structural Features
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    Chapter 11 Expression of Wild Type and Mutant Forms of Human Phenylalanine Hydroxylase in E . Coli
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    Chapter 12 A Re-Examination of the Metal Requirement of Chromobacterium Violaceum Phenylalanine Hydroxylase
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    Chapter 13 Histidines 138 and 143 are copper binding ligands in Chromobacterium violaceum phenylalanine hydroxylase.
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    Chapter 14 Characterization of the Iron Environment in Recombinant Human Tyrosine Hydroxylase, Using Mössbauer and EPR-Spectroscopy
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    Chapter 15 Interaction of Substrate and Pterin Cofactor with the Metal of Human Tyrosine Hydroxylase as Determined by 1 H-NMR
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    Chapter 16 Mechanistic Studies of Tyrosine Hydroxylase
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    Chapter 17 Alleviation of Catecholamine Inhibition of Tyrosine Hydroxylase by Phosphorylation at Serine40
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    Chapter 18 Glyceryl Ether Monooxygenase [EC 1.14.16.5]: Stoichiometry and Inhibition
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    Chapter 19 The Isolation and Characterization of Clones of 4a-Hydroxytetrahydrobiopterin Dehydratase
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    Chapter 20 Molecular Cloning and Recombinant Expression of the Human Liver Phenylalanine Hydroxylase Stimulating Factor Revealed Structural and Functional Identity to the Dimerization Cofactor for the Nuclear Transcription Factor HNF-1α
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    Chapter 21 Progress in the Study of Biosynthesis and Role of 7-Substituted Pterins: Function of Pterin-4a-Carbinolamine Dehydratase
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    Chapter 22 Spectroscopic Characterization of Human Liver Pterin 4a-Carbinolamine Dehydratase
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    Chapter 23 Is Dihydropteridine Reductase an Anomalous Dihydrofolate Reductase, a Flavin-Like Enzyme, or a Short-Chain Dehydrogenase?
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    Chapter 24 Two Crystal Structures of Rat Liver Dyhydropteridine Reductase
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    Chapter 25 New Inhibitors of Dihydropteridine Reductase (Human Brain)
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    Chapter 26 CYS →Ser Mutations in ch-Human Dihydropteridine Reductase
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    Chapter 27 The Spectrum of Mutations in Dihydropteridine Reductase Deficiency
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    Chapter 28 Cloning and Characterization of Genes Encoding Tetrahydrobiopterin Biosynthetic Enzymes
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    Chapter 29 Drosophila GTP Cyclohyrodrolase: Multiple Isoform Products of a Single Gene Derive from Alternate Transcripts that are Developmentally Regulated and Functionally Specific
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    Chapter 30 Studies on GTP Cyclohydrolase I of Escherichia Coli
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    Chapter 31 Partial Purification and Characterization of GTP Cyclohydrolase I from Spinach Leaves
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    Chapter 32 Detection and Quantification of GTP Cyclohydrolase I m RNA
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    Chapter 33 Localization of GTP cyclohydrolase I (GTPCH) mRNA in the rat brain by in situ hybridization.
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    Chapter 34 Expression of GTP cyclohydrolase I (GTPCH) mRNA in the rat: tissue distribution and effect of reserpine.
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    Chapter 35 Regulation of Tetrahydrobiopterin Biosynthesis in Cultured Hypothalamic and Mesencephalic Neurons by Cyclic AMP Dependent GTP Cyclohydrolase I Gene Expression
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    Chapter 36 Mycophenolic Acid Simultaneously Reduces Intracellular GTP and Tetrahydrobiopterin Levels in Neuro-2A Cells
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    Chapter 37 Human Liver 6-Pyruvoyl-Tetrahydropterin Synthase: Expression of the cDNA, Purification and Preliminary Characterization of the Recombinant Protein
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    Chapter 38 Enzymatic Properties of 6-Pyruvoyl Tetrahydropterin Synthase Purified from Fat Bodies of Silkworm Larvae
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    Chapter 39 Northern blot analysis of sepiapterin reductase mRNA in mammalian cell lines and tissues.
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    Chapter 40 Purification and Properties of Human Sepiapterin Reductase from Placenta
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    Chapter 41 Stimulation of Tetrahydrobiopterin Synthesis by Cytokines in Human and in Murine Cells
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    Chapter 42 Interferon-γ and Kit Ligand are Primary Regulators of GTP Cyclohydrolase Activity: Mechanisms and Implications
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    Chapter 43 Differential metabolism of tetrahydrobiopterin in monoamine neurons: a hypothesis based upon clinical and basic research.
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    Chapter 44 Tissue Distribution of Tetrahydrobiopterin Generating Enzymes
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    Chapter 45 Co-Induction of Tetrahydrobiopterin (BH 4 ) Levels and Tyrosine Hydroxylase Activity in Cultured PC12 Cells
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    Chapter 46 Long-Term Treatment of PC12 Pheochromocytoma with Dibutyryl Cyclic Amp Increases Biopterin Content in the Cells but Decreases that in the Medium
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    Chapter 47 Nicotinic Cholinergic Regulation of Tetrahydrobiopterin Levels in Bovine Adrenal Chromaffin Cells
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    Chapter 48 Inter-relationships between pterins and cytokines produced during allogeneic immune reactions and possible use as early markers of immune activation.
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    Chapter 49 An Example of the Detection of an Esophageal Carcinoma in Its Very Early Stage by Urinary Xanthopterin Determination
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    Chapter 50 Neopterin in Subacute Sclerosing Panencephalitis
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    Chapter 51 The 7-Deazaguanine Derivative, Queuine, Regulates Mammalian Cell Proliferation Depending on the Metabolic State
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    Chapter 52 Tetrahydrobiopterin Deficiency and an International Database of Patients
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    Chapter 53 Tetrahydrobiopterin Deficiency in Portugal: Results of the Screening for Hyperphenylalaninemia
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    Chapter 54 A Microtitre Plate Method for Measuring Biopterin with Cryopreserved Crithidia Fasciculata
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    Chapter 55 Oral Administration of Liposomally Entrapped Tetrahydrobiopterin
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    Chapter 56 Experimental Research on a Fetal Treatment for Tetrahydrobiopterin Deficiency
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    Chapter 57 Experimental Research on a New Treatment for Maternal Phenylketonuria(PKU)
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    Chapter 58 Nitric Oxide Synthase: Function and Mechanism
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    Chapter 59 Macrophage Nitric Oxide Synthase: Tetrahydrobiopterin Decreases the Nadph Stoichiometry
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    Chapter 60 Role of Tetrahydrobiopterin in Cytokine-Stimulated Metabolism of Tryptophan and Hydroxylation of Arginine
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    Chapter 61 Tetrahydrobiopterin Synthesis is Induced by LPS in Vascular Smooth Muscle and is Rate-Limiting for Nitric Oxide Production
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    Chapter 62 6R-[ 3 H]Tetrahydrobiopterin Binding Activities in Rat Brain
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    Chapter 63 Inducible Nitric Oxide Synthase Activity in Hepatocytes is Dependent on the Coinduction of Tetrahydrobiopterin Synthesis
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    Chapter 64 Modulation of Nitric Oxide Synthase Activity in Intact Cells by Intracellular Tetrahydrobiopterin Levels
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    Chapter 65 6R-L-erythro-5,6,7,8-Tetrahydrobiopterin: A Regulator of Neurotransmitter Release
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    Chapter 66 Positron Emission Tomography Studies on Some Neurotransmitter Receptor Systems with 6R-Tetrahydrobiopterin Pretreatment
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    Chapter 67 Positron Emission Tomography (PET) Study: The Effects of 6R-L-Erythro-5,6,7,8-Tetrahydrobiopterin (R-THBP, SUN 0588) on the Central Dopamine D 1 , D 2 and D 3 Receptors in Rhesus Monkey
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    Chapter 68 6R-L-Erythro-5,6,7,8-Tetrahydrobiopterin (R-THBP, SUN 0588) Acts on the Brain Muscarinic and Nicotinic Cholinergic Receptors as Evaluated by Positron Emission Tomography (PET) in Rhesus Monkey
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    Chapter 69 Effect of 6R-Tetrahydrobiopterin on the Central Muscarinic Cholinergic Receptor as Evaluated by Positron Emission Tomography Studies Using Rhesus Monkey
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    Chapter 70 Increase of Tetrahydropterins in Cell-Free Retinal Extracts in Response to Light Exposure
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    Chapter 71 Effect of Triamterene on the Electroretinogram of Long Evans Rats
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    Chapter 72 Immunoenzymatic Labeling of Biopterin and Neopterin in the Pigment Epithelium of Bovine Retina
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    Chapter 73 Reduced Pterins as Scavengers for Reactive Oxygen Species
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    Chapter 74 Chemistry and biology of the molybdenum cofactors.
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    Chapter 75 Studies on the Molybdenum Coactor. Synthesis of (±)-Form B (Dephospho)
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    Chapter 76 Molybdenum-Pterin Complexes: A Functional and Structural Model for the Binding Site in the Enzyme Dimethyl Sulfoxide Reductase
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    Chapter 77 Human molybdenum cofactor deficiency.
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    Chapter 78 Molybdopterin biosynthesis in man. Properties of the converting factor in liver tissue from a molybdenum cofactor deficient patient.
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    Chapter 79 Cloning of a Eukaryotic Molybdenum Cofactor Gene
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    Chapter 80 Design and Synthesis of Inhibitors of Folate Dependent Enzymes as Antitumor Agents
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    Chapter 81 Synthesis and Antitumor Activity of LY288601, the 5,6-Dihydro Analog of LY231514
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    Chapter 82 Synthesis and Preliminary Biological Evaluation of Analogues of 5,8-Dideazaisofolic Acid and its 2-Desamino-2-Methyl Derivative Containing Fluorine at Position Five
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    Chapter 83 Synthesis and Biological Evaluation of Analogues of 5,8-Dideazaisofolic Acid (IAHQ) Modified at Positions 2, 4 and 9
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    Chapter 84 New Thiophene Substituted 10-Deazaaminopterins: Synthesis and Biological Evaluation
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    Chapter 85 Evaluation of the Anti-Arthritic Activity and an Alternate Synthesis of a Thiophene-Substituted 10-Deazaaminopterin
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    Chapter 86 Lipophilic Antifolates as Candidates against Opportunistic Infections
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    Chapter 87 Analogues of classical antifolates bearing naphthoyl in place of benzoyl.
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    Chapter 88 Synthesis and Biological Activity of Tricyclic, Conformationally Restricted Analogs of Lipophilic Pyrido[2,3- d ]-Pyrimidine Antifolates
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    Chapter 89 Novel 2,4-Diamino-5-Substituted Furo[2,3- d ]-Pymmidines as Potential Antifolates
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    Chapter 90 Bicyclic Conformationally Restricted Analogs of Nonclassical Pyrido[2,3- d ] Pyrevddines as Potential Inhibitors of Dihydrofolate Reductases
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    Chapter 91 Synthesis, structural and biochemical characterization of cytostatic methotrexate-gamma-glutamyl-glutathione conjugates.
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    Chapter 92 Activation by Peptidases and Cytotoxicity of 2-(L-α-Aminoacyl) Prodrugs of Methotrexate
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    Chapter 93 Effect of a Novel Antifolate, N α -(4-Amino-4-Deoxypteroyl)-N δ -Hemiphthaloyl-L-Ornithbsfe (PT523), On Growth of H35 Rat Hepatoma and HEPG2 Human Hepatoma Cells
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    Chapter 94 Tubulin Binding Properties of Two Chiral Isomers with 1-Deaza-7, 8-Dihydropteridine Structure
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    Chapter 95 Effects of Folic Acid on Pyrimethamine Teratogenesis in Rats
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    Chapter 96 Mutations of Human Dihydrofolate Reductase Causing Decreased Inhibition by Methotrexate
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    Chapter 97 Conformational Analysis of Human Dihydrofolate Reductase Inhibitor Complexes: Crystal Structure Determination of Wild Type and F31 Mutant Binary and Ternary Inhibitor Complexes
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    Chapter 98 Computer-Aided Design of Mechanism-Based Pterin Analogues and MD/FEP Simulations of Their Binding to Dihydrofolate Reductase
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     Chapter 99 Does R67 Dihydrofolate Reductase Possess a Proton Donor?
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     Chapter 100 Laser-Sensitized Tautomers in Dihydrofolate Reductase
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     Chapter 101 Methotrexate-Insensitive Mutants of Human Dihydrofolate Reductase (hDHFR) Constructed by Site Directed Mutagenesis at Phenylalanine 34
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     Chapter 102 Kinetic Investigation of Methotrexate Resistant Human Dihydrofolate Reductase (hDHFR) Mutants at PHE 31
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     Chapter 103 The Effect of Codon 31 on the Relative Affinities for the Binding of Designed 8-Alkyl-Pterins to Dihydrofolate Reductase: A Statistical Perturbation Theory and Molecular Dynamics Simulation Study
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     Chapter 104 Effect of Codon 22 Mutations on Substrate and Inhibitor Binding for Human Dihydrofolate Reductase
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     Chapter 105 Thermodynamic Study of Folate Analogue Binding to Dihydrofolate Reductases from Different Species
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     Chapter 106 Comparison of Binding and Activity of 8-Alkyl-Pterins and 8-Alkyl-N5-Deaza-Pterins with Dihydrofolate Reductase
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     Chapter 107 Development of a Spectrofluorimetric Method for Determining the p K a of Pterin-Analogue Ligands Bound to DHFR
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     Chapter 108 Selective Inhibition of Dihydrofolate Reductase from Problem Human Pathogens
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     Chapter 109 Translational regulation of the synthesis of dihydrofolate reductase.
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     Chapter 110 Expression of the Trimethoprim Resistant Dihydrofolate Reductase Encoded by Transposon TN4003 in a Soluble Form and Its Subsequent Purification to Homogeneity
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     Chapter 111 Effect of Genomic Position on Amplification of the DFR 1 Gene in Saccharomyces Cerevisiae
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     Chapter 112 Dihydrofolate Reductase is not the Target of Trimethoprim in Saccharomyces Cerevisiae
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     Chapter 113 Point Mutations in the Dihydropteroate Synthase Gene Causing Sulfonamide Resistance
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     Chapter 114 Frequent Amplification of a Short Chain Dehydrogenase Gene in Methotrexate Resistant Leishmania
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     Chapter 115 Enzyme Interactions Involving T4 Phage-Coded Thymidylate Synthase and Deoxycytidylate Hydroxymethylase
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     Chapter 116 Isolation of Cdnas Encoding Thymidylate Synthase from Soybean Seedlings and Expression of the Protein in E . Coli
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     Chapter 117 Use of 10-Propargyl-5,8-Dídeazafolate and Directed Mutagenesis to Probe the Catalytic Mechanism of Thymidylate Synthase
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     Chapter 118 Gamma-linked dipeptide analogues of 2-desamino-2-methyl-N10-propargyl-5,8- dideazafolate as antitumour agents.
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     Chapter 119 Substituted-2-Desamino-2-Methyl-Quinazolinones. A Series of Novel Antitumour Agents
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     Chapter 120 Use of Murine L5178Y Lymphoma Thymidine Kinase Mutants for in Vitro and in Vivo Antitumour Efficacy Evaluation of Novel Thymidylate Synthase Inhibitors
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     Chapter 121 Quinazoline Antifolates Inhibiting Thymidylate Synthase: Synthesis of γ-Linked Peptide and Amide Analogues of 2-Desamino-2-Methyl-N 10 -Propargyl-5,8-Dideazafolic Acid (ICI 198583) 10 -Propargyl-5,8-Dideazafolic Acid (ICI 198583)
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     Chapter 122 The Duration of the Inhibition of Thymidylate Synthase in Intact L1210 Cells Exposed to Two Different Classes of Quinazoline Analogues
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     Chapter 123 The Toxicity of ICI D1694 in Man and Mouse
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     Chapter 124 Evaluation of Immunohistochemical Staining and Activity of Thymidylate Synthase in Cell Lines
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     Chapter 125 The Interval Between Methotrexate and Leucovorin Determines the Efficacy of 5-Fluorouracil Modulation in Vitro and in Vivo
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     Chapter 126 Potentiation of 5-Fluorouracil Induced Inhibition of Thymidylate Synthase in Human Colon Tumors by Leucovorin is Dose Dependent
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     Chapter 127 Interaction with 2(4)-Thio-5-Fluoro-dUMP of Thymidylate Synthases with Differing Sensitivities to 5-Fluoro-dUMP
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     Chapter 128 Mechanism of Thymidylate Synthase Inhibition by N 4 -Hydroxy-(N 4 -Hydroxy-5-Fluoro)-dCMP in View of the Structure and Conformation of N 4 -Hydroxy-(N 4 Hydroxy-5-Fluoro)-Cytosine Calculated by the Ab Initio Quantum Mechanical Methods
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     Chapter 129 Sulphonamide Antifolates Inhibiting Thymidylate Synthase. Synthesis, Enzyme Inhibition and Cytotoxicity
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     Chapter 130 Folylpoly-γ-Glutamate Synthetase
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     Chapter 131 Increased activity of gamma-glutamyl hydrolase in human sarcoma cell lines: a novel mechanism of intrinsic resistance to methotrexate (MTX).
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     Chapter 132 Mechanism-based approaches to inhibition of the synthesis and degradation of folate and antifolate polyglutamates.
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     Chapter 133 Polyglutamate Product Formation by Lactobacillus Casei Folylpolyglutamate Synthetase in Vitro and in Vivo in Recombinant Escherichia Coli
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     Chapter 134 Development of a Simple Folylpolyglutamate Synthetase Assay in Tissues and Cell Lines
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     Chapter 135 Two Novel HPLC Methods which Rapidly Detect the Substrates and Cleavage Products of γ-Glutamyl Hydrolase
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     Chapter 136 Purification and General Properties of Human Folylpolyglutamate Synthetase
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     Chapter 137 Antitumor Efficacy of Classical Non-Polyglutamylatable Antifolates that Inhibit Dihydrofolate Reductase
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     Chapter 138 Studies on the Cross-Resistance of Folylpolyglutamate Synthetase-Deficient, Methotrexate-Resistant CCRF-CEM Human Leukemia Sublines
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     Chapter 139 Variable Pharmacodynamics of Antifolates in Squamous Cell Carcinoma of the Head and Neck
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     Chapter 140 Metabolism of Folate Glutamates in Aspergillus Nidulans
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     Chapter 141 Evidence that 5-formyltetrahydropteroylglutamate has a metabolic role in one-carbon metabolism.
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     Chapter 142 Cobalamin-dependent and cobalamin-independent methionine synthases in Escherichia coli: two solutions to the same chemical problem.
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     Chapter 143 Folate Metabolites as Modulators of Antitumor Drug Activity
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     Chapter 144 MTX Does Not Affect Enhanced Biosynthesis and Metabolism of S-Adenosylmethionine in Testosterone-Induced Hypertrophic Mouse Kidney
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     Chapter 145 Thermolability of Residual Methylenetetrahydrofolate Reductase (MR) Activity, Methionine Synthase Activity and Methyl-Cobalamin Levels in Cultured Fibroblasts from Patients with MR Deficiency
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     Chapter 146 Enzymes For Synthesis of 10-Formyltetrahydrofolate in Plants: Characterization of a Monofunctional 10-Formyltetrahydrofolate Synthetase and Copurification of 5,10-Methylenetetrahydrofolate Dehydrogenase and 5,10-Methenyltetrahydrofolate Cyclohydrolase Activities
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     Chapter 147 Cloning of the Genes Encoding the Serine Hydroxymethyltransferases from Saccharomyces Cerevisiae
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     Chapter 148 Serine Hydroxymethyltransferase: Role of the Active Site Lysine in the Mechanism of the Enzyme
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     Chapter 149 Purification of Neurospora Crassa Cytosolic Serine Hydroxymethyltransferase
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     Chapter 150 Purification and properties of rabbit liver 5,10-methenyltetrahydrofolate synthetase.
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     Chapter 151 Folate Metabolism in Pregnancy
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     Chapter 152 Influence of Gestation and Lactation on the Levels of Plasma Folates in Sows
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     Chapter 153 Identification of Endogenous Tetrahydrofolate and 10-Formyltetrahydrofolate as Major Folates in Rat Bile
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     Chapter 154 Development of a Sensitive Assay for Detection of Uracil in DNA
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     Chapter 155 5-Methyltetrahydrofolate Urinary Excretion: Modeling by Cultured Human Kidney Cells
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     Chapter 156 Contribution of Plasma Protein Binding to the Stability of Tetrahydrofolate in Pig Plasma
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     Chapter 157 Ligand Induced Conformation Change in Folate Binding Protein
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     Chapter 158 The High-Affinity Folate Binding Protein in Normal and Malignant Mammary Gland Tissue
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     Chapter 159 Detergent-Insolubility During the Biosynthesis of Membrane Folate Receptor-2
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     Chapter 160 The Reduced Folate/Methotrexate Carrier and a Membrane-Associated Folate Binding Protein as Transport Routes for Novel Antifolates: Structure-Activity Relationships
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     Chapter 161 Identification of a Reduced Folate/Methotrexate Carrier in Human KB-Cells Expressing High Levels of Membrane Associated Folate Binding Protein
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     Chapter 162 Altered Transport of Folic Acid and Antifolates Through the Carrier Mediated Reduced Folate Transport System in a Human Leukemia Cell Line Resistant to (6R) 5,10-Dideazatetrahydrofolic Acid (DDATHF)
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     Chapter 163 Transformation of an L-Cell Line with the DNA Coding for the Reduced-Folate/Methotrexate Transporter Protein from a CCRF-CEM Human Leukemia Cell Line
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     Chapter 164 Determinants of the Disparate Antitumor Effects of (6R)5,10-Dideaza-5,6,7,8-Tetrahydrofolate and Methotrexate Toward Methotrexate Resistant CCRF-CEM Cells, Characterized by Severely Impaired Antifolate Membrane Transport
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     Chapter 165 Up-regulated transport of methotrexate and 5-methyl-tetrahydrofolate in a human breast cancer cell line.