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Zurich, Switzerland, September 3–8, 1989
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Table of contents
- 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)-N<sup>5</sup>-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 H<sub>4</sub>biopterin and related compounds
- The structure of<sub>q</sub>-Bh<sub>2</sub> - 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 reconstitutß<sub>60</sub>, 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 BH<sub>4</sub>, 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 BH<sub>4</sub> on the synthesis of serotonin in brain slices and synaptosomes: implications for the use of BH<sub>4</sub> 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
- 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 H<sub>4</sub>PteGlu/5,10-CH<sub>2</sub>-H<sub>4</sub>PteGlu ratios; and H<sub>4</sub>PteGlu-catalyzed release of fluoride ion from alpha-fluoro-beta alanine.
- Interaction of N<sup>4</sup>-hydroxy-dCMP and N<sup>4</sup>-hydroxy-5-FdCMP with L1210 thymidylate synthase differing in sensitivity towards 5- FdUMP Inhibition
- Mechanism of thymidylate synthase inhibition by N<sup>4</sup>-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 N<sup>10</sup>-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 N<sup>5</sup> 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-CH<sub>3</sub>-N<sup>10</sup>-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-N<sup>10</sup>-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