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Licensed Unlicensed Requires Authentication Published by De Gruyter 1990

Biochemical pharmacology of deazatetrahydrofolates

From the book 9 Zurich, Switzerland, September 3–8, 1989

  • D. Wildman , A.D. Cross , B.A. Moroson , A.R. Cashmore , O. Russello , G. Pizzorno , G.P. Beardsley and G.B. Grindey
https://doi.org/10.1515/9783110889000-192
© 2019 Walter de Gruyter GmbH, Berlin/Munich/Boston
From the book
9 Zurich, Switzerland, September 3–8, 1989
9 Zurich, Switzerland, September 3–8, 1989

Chapters in this book (250)

Frontmatter
Preface
Adrien Albert
Alois Niederwieser
Tetsuo Shiota
Contents
I CHEMISTRY OF PTERINS AND FOLATES
Recent progress in pteridine chemistry
Synthesis of pteridines for immunoassay of biopterin and neopterin isomers
Design of new mechanism-based substrates for dihydrofolate reductase
New methods for the synthesis of quinazoline antifolates and poly-y-glutamyl metabolites of folates and antifolates
The decay of quinoid- and 7,8-dihydropterins
Synthesis of 6-acetyl-2,4-diamino-7,8-dihydro-9//-pyrimido-[4,5-b][l,4]- diazepine, an amino analog of 6-acetyldihydrohomopterin
Synthetic approaches to methanopterin
Synthesis and properties of tetrahydropterins coupled to 1,4-dihydropyridines
A new synthesis of biopterin and some analogues from epoxyaldehydes
Synthetic studies on the molybdenum cofactor
A new regiospecific synthesis of anapterin and primapterin
A novel and efficient synthesis of folylpolyglutamates
Reaction of acidic anhydride and pyridine with folic acid and classical antifolates
Quinazoline antifolate thymidylate synthase inhibitors: Synthesis of analogues containing heterocyclic isosteres of the para-aminobenzoate unit
Synthesis of tetrahydro-8-deazabiopterin
Synthesis and enzymic properties of new mechanism based substrates for dihydrofolate reductase of the 8-substituted pterin class.
Imidazolines as carbon-transfer vehicles: models of the tetrahydrofolate (and other) coenzymes
Asymmetric synthesis and absolute configuration of 5,10-dideaza- 5,6,7,8-tetrahydropteroic acid and 5,10-dideaza-5,6,7,8-tetrahydrofolic acid
Synthesis and biological evaluation of a fluorescent analogue of folic acid
Metal complexes of tetrahydroneopterin
Syntheses of lipophilic analogues of 2-desamino-2-CH3-NIO-propargyl- 5,8-dideazafolate targeted at the enzyme thymidylate synthase (TS).
Studies in models of folate cofactors: oxidation of 5-methyltetrahydropterin revisited.
New strategy in the synthesis of neopterin phosphates
First regiospecific synthesis of 7-iso-D-neopterin and 7-iso-D-neopterin- 3 '-monophosphate
II. ANALYSIS OF PTERINS AND FOLATES
Detection of pterins in biological material using mass spectrometry
Mass spectrometric methods for the structural determination of pteridines and folic acid derivatives
Structural characterization of underivatized pteridines by laser desorption fourier transform mass spectrometry
New immunoassays for determination of biopterin and neopterin in body fluids
A new immunoassay for neopterin and biopterin
Enzyme immunoassay for urinary neopterin
A competitive enzyme linked ligand sorbent assay (ELLSA) for quantitation of erythrocyte folates
Preparation of a bovine serum albumin based chiral matrix for resolution of (6R,S)-N5-formyltetrahydrofolate.
Rp-HPLC methods for the isolation and chemical identification of pterins from monocytic blood cells
Cyclodextrin based HPLC separation of 6-S and 6-R diastereomers of 5,10-dideaza and 5-deazatetrahydrofolates.
Analysis of folate and antifolate metabolites by mass spectrometry
A critical assessment of methods for measuring folate in human serum and red blood cells.
HPLC analysis of intracellular folate compounds after enzymic conversion to the corresponding pteroates
III. BIOSYNTHESIS AND BIOCHEMISTRY OF PTERINS
The Gowland Hopkins Lecture: Biosynthesis of H4biopterin and related compounds
The structure ofq-Bh2 - chemistry and biochemistry
Pteridines in riboflavin biosynthesis
Pteridine mimicking antibodies
6-Pyruvoyl-tetrahydropterin reductases
Analysis of 6-pyruvoyl tetrahydropterin synthase, a target gene product of su(s) suppressor in Drosophila
Synthesis of fluorinated 8-ribityllumazines as "F NMR probes and potential inhibitors of the light riboflavin synthase of Bacillus subtilis
Studies on the oxidation state and biosynthesis of molybdopterin
Molybdenum cofactor genes in Drosophila
DNA photolyase: role of pterin in DNA repair.
7-Substituted pterins, a new class of mammalian pteridines
Methanopterin: A structural and functional folic acid analogon in the biochemistry of methanogenic bacteria.
Biosynthesis of methanopterin
Tetrahydrobiopterin is required for the oxidation of arginine to nitric oxide by macrophages.
Biosynthesis of 7-hydroxybiopterin
GTP cyclohydrolase I from Escherichia coli. Molecular cloning and crystallization
Molecular characterization of the GTP cyclohydrolase I gene of Drosophila: analysis of cDNA clones
Inhibitors of bovine adrenal medullary sepiapterin reductase
Catalytic implication of the reductase and isomerase activity of sepiapterin reductase in the biosynthesis of tetrahydrobiopterin
Purification and characterization of sepiapterin reductase from human liver
Biosynthesis of methanopterin and deazaflavin in Methanobacterium thermoautotrophicum
Studies on riboflavin synthases of Bacillus subtilis. Amino acid sequence of the a subunit
Structure of the lumazine synthase/riboflavin synthase complex of Bacillus subtilis: crystallization of hollow reconstitutß60, capsids.
Biosynthesis of 6,7-dimethyl-8-ribityllumazine. Purification and properties of 3,4-dihydroxy-2-butanone 4-phosphate synthase
High resolution electron microscopy on crystals of the icosahedral lumazine synthase/riboflavin synthase complex.
Differential synthesis of LDH A-like proteins and of phosphoproteins in response to the modified deazaguanine-derivative queuine
Metabolic control in HeLa-cells mediated by the deazaguanine-derivative queuine
On the biosynthesis of the deazaguanine-derivative queuine: structure of the tgt gene of E. coli
Changes in the level of biopterin and of queuine-containing tRNA during erythroid differentiation of murine erythroleukemia cells
Brain contents of biopterins and monoamines after intraperitoneal injections of SUN0588, active 6R-tetrahydrobiopterin, during ontogeny in rats
The effect of 2,4-diamino-6-hydroxypyrimidine on tetrahydrobiopterin and serotonin in the gastrointestinal tract of mice.
Differential metabolism of tetrahydrobiopterin in central and peripheral monoamine neurons maintained in culture
IV. TETRAHYDROBIOPTERIN DEFICIENCY
Inborn errors in tetrahydrobiopterin metabolism
Molecular defects in dihydropteridine reductase deficiency
Screening and treatment of tetrahydrobiopterin deficiency
Tetrahydrobiopterin deficient phenylketonuria detected by neonatal screening in Taiwan
Prenatal diagnosis of 6-pyruvoyl tetrahydropterin synthase deficiency in East Asia.
Heterogeneity of tetrahydrobiopterin deficiency: combined phenylalaninetetrahydrobiopterin loading test
Unusual case of atypical PKU: peripheral or central form of PPH4S deficiency
Development of vision in BH4, deficiency
Fetal guinea-pig model of tetrahydrobiopterin deficiency
Unexpected favorable clinical results of therapy in late diagnosed DHPR deficiency
Systematic investigation for biopterin defects in hyperphenylalaninemic patients
Neuroradiological improvement after one year of therapy in a case of DHPR deficiency
V. PTERINS VARIOUS
Lumazine protein and the bioluminescence of photobacterium
Binding of pteridine derivatives to lumazine apoprotein
Hormonal imbalance by pteridine treatment in diapausing Pieridae induces mutations in the progeny of treated Drosophila melanogaster
N-acetyltransferase activity in Pieris brassicae
VI. BIOLOGY OF PTERINS
Pteridines and the immune response.
Neopterin elevation and interferon induction in viral diseases
Tetrahydrobiopterin in human T cells: control of its biosynthesis by interferon-y and interleukin 2 - modulator function in interleukin 2 perception
Effects of BH4 on the synthesis of serotonin in brain slices and synaptosomes: implications for the use of BH4 as a therapeutic agent
Regulation of cellular proliferation by tetrahydrobiopterin
Characterisation of the mutation in dihydropteridine reductase deficiency
Urinary excretion of total pteridines in cancer
Alterations of interferon-gamma-induced monocyte activation by immunomodulating compounds determined by neopterin production
Levels of neopterin, biopterin, 5-hydroxyindoleacetic acid, and homovanillic acid in cerebrospinal fluid of sick neonates and infants
Urinary neopterin levels in healthy children
Urinary neopterin factor in viral and bacteriological children infections
Urinary neopterin levels in liver transplant
The effect of IL-2, neopterin and immunomodulators on neopterin release from macrophages and PBMC
Membrane transport of unconjugated pteridines. The model of human erythrocytes.
Encephalopathy and abnormal cerebrospinal fluid pteridine profile. Fact or artefact ?
Informativity of pteridine measurements in the survey of organ transplantations
Effect of triamteren on urinary excretion of pterins in different rat strains
Pteridines and retinal degenerations in rats and humans
Pterins in bovine, rat, quail and human retina
Comparison of urinary biopterin in rats with various housing and enviromental conditions
Differences in the quantity and distribution of urinary pterins in various species of mammals
Total biopterin levels in the ventricular CSF of Parkinson's disease and essential tremor
Urinary xanthopterin and derivatives as indicators of liver disease
Genetic control of dihydropterin oxidase activity in Drosophila melanogaster
A controlled system for supplementation experiments in Drosophila melanogaster
New eye-color mutants affecting the biosynthesis of pteridines and ommochromes in Drosophila melanogaster
Search for 6- and 7-biopterins in human saliva
VII. TETRAHYDROBIOPTERIN-DEPENDENT MONOOXYGENASES
Regulation of the aromatic amino acid hydroxylases
Expression of rat liver dihydropteridine reductase in Escherichia coli
Escherichia coli dihydropteridine reductase is a trifunctional enzyme with dihydrofolate reductase activity.
Rat liver preparations with glyceryl etherase activity
Purification and characterization of a membrane associated folate binding protein from human leukemic CCRF-CEM cells
On the effects of high protein diet and of starvation on phenylalanine hydroxylase activities in rats.
Effects of experimental diabetes on phenylalanine hydroxylase activities in rats
Molecular defects of PKU in Italy differ from those of other European countries
The oxidation of tetrahydropteridines by phenylalanine hydroxylase
Interaction of catecholamines and tetrahydropterins with bovine liver phenylalanine hydroxylase
Studies of tetrahydrobiopterin uptake in rat brain synaptosomes
The influence of cofactor side-chain chirality on the activity and regulation of phenylalanine and tyrosine and hydroxylases
Limited denaturation stimulates tetrahydrobiopterin-dependent activity of rat liver phenylalanine hydroxylase
Effect of limited proteolysis on structure and activity of phenylalanine hydroxylase
Tetrahydropterin as a possible natural cofactor in the Drosophila phenylalanine hydroxylation system
Interaction of substrate analog inhibitors with rat liver dihydropteridine reductase
Simultaneous purification of phenylalanine hydroxylase, phenylalanine hydroxylase stimulator protein, and dihydropteridine reductase from rat liver
VIII. FOLATES
A. DIHYDROFOLATE REDUCTASE
NMR and mutagenesis studies of dihydrofolate reductase
Spectroscopic studies of the interaction of ligands with dihydrofolate reductase
Comparison between human and bacterial dihydrofolate reductase structures
Mutagenesis of human dihydrofolate reductase structure as a probe of enzyme function
Folate and dihydrofolate reduction by mouse dihydrofolate reductase
Kinetic mechanism of recombinant human dihydrofolate reductase
The kinetic mechanism of the reaction catalyzed by an R-plasmid (R-67) dihydrofolate reductase from E.coli.
Mechanism based inhibitors of dihydrofolate reductase.
Trimetrexate resistant L. casei and S. faecium
Second site revertants of E. coli dihydrofolate reductase
Structural and energetic aspects of the reaction pathway and transition state for hydride-ion transfer in dihydrofolate reductase
Cloning of trimethoprim-resistant dihydrofolate reductase from multiresistant staphylococci and expression in E. coli
Role of TRP-24 in binding and catalysis for human dihydrofolate reductase (DHFR)
Mutation at hydrophobic residues in dihydrofolate reductase
Determination of the functional role of phenylalanine-31 of recombinant human dihydrofolate reductase by site-directed mutagenesis
Molecular modeling studies and crystal structure determination of pteridine antifolate-DHFR enzyme interactions
Allelic variants of Chinese hamster dihydrofolate reductase
B: THYMIDYLATE SYNTHASE
Thymidylate synthase - structural and functional considerations
Defining the catalytic role of specific amino acids in thymidylate synthase by site-specific mutagenesis
Studies of the effects of mutagenesis on a conserved active site arginine residue in thymidylate synthase
Dual role of serine hydroxymethyltransferase in the synergy of fluorouracil and leucovorin: effects of L-serine and glycine on H4PteGlu/5,10-CH2-H4PteGlu ratios; and H4PteGlu-catalyzed release of fluoride ion from alpha-fluoro-beta alanine.
Interaction of N4-hydroxy-dCMP and N4-hydroxy-5-FdCMP with L1210 thymidylate synthase differing in sensitivity towards 5- FdUMP Inhibition
Mechanism of thymidylate synthase inhibition by N4-Hydroxy-dCMP
Thymidylate synthase activity in bronchoalveolar lavage cells as a possible marker in lung cancer diagnosis
Purification and properties of Hymenolepis diminuta and regenerating rat liver thymidylate synthases
Influence of FdUMP on the binding of methotrexate to thymidylate synthase
Efficient expression of mammalian thymidylate synthase in Escherichia coli
Catalytic role of histidine-147 in Escherichia coli thymidylate synthase
Variation among human thymidylate synthase enzymes in folate affinity
Evaluation of in vivo inhibition of thymidylate synthase in patients with colorectal cancer treated with 5-fluorouracil
Effect of leucovorin on 5-fluorouracil induced inhibition of thymidylate synthase in murine colon cancer
Feedback inhibition of thymidylate synthase by dihydrofolate polyglutamates cannot account for partial depletion of tetrahydrofolate cofactors by antifolates
Kinetic studies on thymidylate synthase from Lactobacillus casei
C. METHIONINE SYNTHASE
Studies on the cobalamin-dependent methionine synthase from Escherichia coli K12
Foimyl phosphate as an intermediate in the N10-formyltetrahydrofolate synthetase reaction.
Enzymes of homocysteine remethylation and transsulfuration in methionine or cholesterol induced atherosclerosis in rabbits
Biochemical changes in porcine neural tissue after inactivation of methionine synthase by nitrous oxide.
Increased synthesis of AdoMet but not of methionine during testosterone stimulation of polyamine biosynthesis in mouse kidney
D. ENZYMOLOGY AND METABOLISM
Role of folylpolyglutamate synthetase in the regulation of folate and antifolate metabolism.
NAD-dependent methylenetetrahydrofolate dehydrogenase-cyclohydrolase present in transformed mammalian cells
Gammaglutamyl hydrolases
Human methenyltetrahydrofolate synthetase
Folate catabolism in man and the rat
Effects of growth rate on y-glutamyl hydrolase in Ehrlich ascites carcinoma cells
Folylpolyglutamate synthesis in Neurospora crassa. Wild type FPGS activity and transformation of polyglutamate deficient mutants using cosmid vectors containing the met-6 gene
Cloning and expression of the gene encoding Lactobacillus casei folylpolyglutamate synthetase in Escherichia coli
Effect of treatments with different anticonvulsant drugs on folate pattern in rat liver.
A sensitive new microassay useful for measurement and purification of mammalian folylpolyglutamate synthetase
Tissue differences in N5 formyltetrahydrofolate metabolism
E. FOLATES IN ENDOGENOUS PURINE METABOLISM
Glycinamide ribonucleotide transformylase from E. coli: characterization and inhibition.
Estimation of the flux control coefficient of glycineamide ribonucleotide transformylase for purine biosynthesis de novo
Monocyclic 5-deazatetrahydrofolate analogues as inhibitors of de novo purine biosynthesis
Inhibition of glycinamide ribonucleotide transformylase, methotrexate transport, and the growth of MCF-7 cells by 5,8-dideazafolates
F. FOLATES, VARIOUS
Formation of methylcobamide from methyltetrahydrofolate by acetogenic bacteria: enzymology and redox chemistry.
Incorporation of the ring carbon of histidine into coenzymes of folylpolyglutamates.
In vivo effect of folic acid on fragile-site expression
IX. ANTIFOLATES
A. DEAZADERIVATIVES
New synthetic studies on deazafolates
Molecular modeling studies on deazatetrahydrofolates
Biochemical pharmacology of deazatetrahydrofolates
Synthesis and evaluation of l-deaza-7,8-dihydropteridines and ring analogues
In vitro and in vivo activity of the GAR transformylase inhibitor 5-deazacyclotetrahydrofolate
vitro and in vivo studies with 2-desamino-2-CH3-N10-propargyl-5,8- dideazafolate (ICI 198583), an inhibitor of thymidylate synthase
Comparative studies on the activity of methotrexate and the analog 10-ethyl-10-deaza-aminopterin (10-EdAM) against head and neck carcinoma cell lines and xenografts.
Transport of 5,10-dideazatetrahydrofolic acid (DDATHF) in CCRF-CEM sensitive and methotrexate resistant cell lines
Synthesis and structure-activity relationship studies of 5,10- dideazatetrahydrofolic acid (DDATHF)
Synthesis and antifolate properties of 5-alkyl-5-deazaaminopterin analogues modified in the 10-position
Synthesis and biological evaluation of 2-desamino-2-methyl-5,10- dideazatetrahydrofolate
Quinazoline antifolate thymidylate synthase inhibitors: potent cytotoxic agents containing heterocyclic isosteres of the para-amino benzoate unit
Antifungal activity of some 2,4-diamino-5-methyl-6-alkyl quinazoline
Membrane transport characteristics of the thymidylate synthase inhibitor 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid.
Synthesis and potential antitumor activity of 5-deaza analogs of 5,10- methylenetetrahydrofolic acid
Theoretical studies of the structures and conformations of triazine antifolates
In vitro and in vivo metabolism of 5-DACTHF, an acyclic tetrahydrofolate analog
Measurement of retained thymidylate synthase (TS) inhibition by antifolates in whole cells in vitro
Substitution on the benzene ring of quinazoline antifolates that inhibit thymidylate synthase
Inhibition of de novo purine synthesis by deazatetrahydrofolates
B.Methotrexates
Resistance to methotrexate in experimental models and in patients
Methotrexate peptides as cancer chemotherapeutic agents
Biochemical determinants of methotrexate selectivity
Mechanisms underlying methotrexate inactivity in human head and neck cancer xenografts
Design and synthesis of novel methotrexate derivatives for antibody directed drug targeting
Methotrexate (MTX) transport and cytotoxity of MTX and trimetrexate (TMQ) for human squamous cell carcinoma (SCC) of the head and neck grown at low folate concentrations
Folate enhancement of antifolate synergism in lymphoma cells
Amino acid oxidation and dihydrofolate reductase inactivation photosensitized by a diaminopteridine
Synchronisation of U937 and SW626 cancer cell lines of human origin using methotrexate
New inhibitors of plasmodial folate synthesis - comparison of cell-free, whole cell and in vivo activities for single drugs and drug combinations
Effect of vincristine on methotrexate cytotoxicity and accumulation in MCF-7 cells, a human breast cancer cell line
The y-tetrazole analog of methotrexate: design, synthesis and biological activity
Effect of intravenous 24 hr infusions of methotrexate on unconjugated pteridine metabolism
Covalent labeling of dihydrofolate reductase and folate transport proteins by fluorescein methotrexate
Study of methotrexate polyglutamate formation in cultured leukemic cells
C. Various Antifolates
Folyl polyglutamates in metabolism and chemotherapy
Biological determination of selective antitumor action of 4-amino-folate analogs
Inhibition of the thymidylate synthase cycle of leukemia cells by antifolates: The usefulness of the cellular tritium release assay
Fluoroglutamate-containing folates and antifols: probing the role of polyglutamylation in vitro
Therapeutic strategies for 5-fluorouracil-leucovorin based upon cellular metabolic characteristics in human colon adenocarcinoma xenografts
The lack of response of human colonic tumor cell lines to biochemical modulation by folinic acid.
Folinic acid as a source of intracellular 5,10-methylenetetrahydrofolate in human carcinoma cells
Structure activity relationships of multidrug resistance
Enhancement of the cytotoxicity of fluoropyrimidines to human carcinoma cell lines by leucovorin
D. Transport And Absorption Of Folates And Antifolates
Methotrexate transport via the high-affinity folate binding protein of L1210 cells.
Combined affinity and ion pair liquid chromatographies for direct analysis of tissue folate composition
Tumor cell sensitivity and resistance to folate analogues: the role of carrierand receptor-mediated transport systems
Lysosomal permeability to methotrexate polyglutamates
Folic acid metabolism in placental cells associated with neural tube defects
Homologous membrane folate binding proteins in human placenta
A high-affinity folate binding protein in human amniotic fluid
Interaction of N-hydroxy(sulfo)succinimide active esters with the reduced folate/methotrexate transport system from human CCRF-CEM leukemia cells
Renal uptake and metabolism of 5-methyltetrahydrofolate in the rat
Methotrexate- and folate-lipid conjugates of defined chemical structures as new antifolate analogs and transport probes
Characterization of receptor-mediated (anti)folate uptake in human CCRF-CEM cells
Author Index
Subject Index
List of Participants
Backmatter
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