316-46-1 | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione

Packsize	Purity	Availability	Price	Discounted Price
1g	98%(HPLC)	in stock	$33.00	$23.00
5g	98%	in stock	$57.00	$40.00
10g	98%	in stock	$98.00	$69.00
25g	98%	in stock	$227.00	$159.00
100g	97%	in stock	$718.00	$502.00

Description

• Catalog Number: AB69283
• Chemical Name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
• CAS Number: 316-46-1
• Molecular Formula: C9H11FN2O6
• Molecular Weight: 262.1918
• MDL Number: MFCD00036832
• SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cc(F)c(=O)[nH]c1=O

Computed Properties

• Complexity: 414
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 4
• Heavy Atom Count: 18
• Hydrogen Bond Acceptor Count: 7
• Hydrogen Bond Donor Count: 4
• Rotatable Bond Count: 2
• XLogP3: -1.7

Literature

• Ligand binding and aggregation of pathogenic SOD1.

  Nature communications 20130423

• Proton transfer from C-6 of uridine 5'-monophosphate catalyzed by orotidine 5'-monophosphate decarboxylase: formation and stability of a vinyl carbanion intermediate and the effect of a 5-fluoro substituent.

  Journal of the American Chemical Society 20120905

• Untargeted metabolomics reveals a lack of synergy between nifurtimox and eflornithine against Trypanosoma brucei.

  PLoS neglected tropical diseases 20120501

• A functional genomics approach to establish the complement of carbohydrate transporters in Streptococcus pneumoniae.

  PloS one 20120101

• Overexpression of the orotate phosphoribosyl-transferase gene enhances the effect of 5-Fluorouracil in head and neck squamous cell carcinoma in vitro.

  Journal of oncology 20120101

• The products of 5-fluorouridine by the action of the pseudouridine synthase TruB disfavor one mechanism and suggest another.

  Journal of the American Chemical Society 20110810

• The therapeutic efficacy of S-1 against orthotopically implanted human pleural mesothelioma cells in severe combined immunodeficient mice.

  Cancer chemotherapy and pharmacology 20110801

• Equilibrative nucleoside transporter 1 (ENT1) is critical for pollen germination and vegetative growth in Arabidopsis.

  Journal of experimental botany 20110801

• Plastid uridine salvage activity is required for photoassimilate allocation and partitioning in Arabidopsis.

  The Plant cell 20110801

• Development of miracle medicines from sialic acids.

  Proceedings of the Japan Academy. Series B, Physical and biological sciences 20110610

• N⁴-[Alkyl-(hydroxyphosphono)phosphonate]-cytidine-new drugs covalently linking antimetabolites (5-FdU, araU or AZT) with bone-targeting bisphosphonates (alendronate or pamidronate).

  Bioorganic & medicinal chemistry 20110601

• Synthesis and biological evaluation of unsaturated keto and exomethylene D-arabinopyranonucleoside analogs: novel 5-fluorouracil analogs that target thymidylate synthase.

  European journal of medicinal chemistry 20110401

• The handling of the mechanistic probe 5-fluorouridine by the pseudouridine synthase TruA and its consistency with the handling of the same probe by the pseudouridine synthases TruB and RluA.

  Biochemistry 20110125

• Proteinortho: detection of (co-)orthologs in large-scale analysis.

  BMC bioinformatics 20110101

• Matrix metalloproteinase-8 mediates the unfavorable systemic impact of local irradiation on pharmacokinetics of anti-cancer drug 5-Fluorouracil.

  PloS one 20110101

• Resistance of a rodent malaria parasite to a thymidylate synthase inhibitor induces an apoptotic parasite death and imposes a huge cost of fitness.

  PloS one 20110101

• Lipopolysaccharide-Deficient Brucella Variants Arise Spontaneously during Infection.

  Frontiers in microbiology 20110101

• Quantitative nucleolar proteomics reveals nuclear re-organization during stress- induced senescence in mouse fibroblast.

  BMC cell biology 20110101

• Checkpoint signaling, base excision repair, and PARP promote survival of colon cancer cells treated with 5-fluorodeoxyuridine but not 5-fluorouracil.

  PloS one 20110101

• Topical delivery of DNA oligonucleotide to induce p53 generation in the skin via thymidine dinucleotide (pTT)-encapsulated liposomal carrier.

  International journal of nanomedicine 20110101

• 13C/15N-19F intermolecular REDOR NMR study of the interaction of TAR RNA with Tat peptides.

  Journal of the American Chemical Society 20101222

• Gene annotation and drug target discovery in Candida albicans with a tagged transposon mutant collection.

  PLoS pathogens 20101001

• Glycosidic bond conformation preference plays a pivotal role in catalysis of RNA pseudouridylation: a combined simulation and structural study.

  Journal of molecular biology 20100903

• PfNT2, a permease of the equilibrative nucleoside transporter family in the endoplasmic reticulum of Plasmodium falciparum.

  The Journal of biological chemistry 20100702

• Development and validation of a rapid and sensitive HPLC method for the quantification of 5-fluorocytosine and its metabolites.

  Biomedical chromatography : BMC 20100501

• Selective targeting of 2'-deoxy-5-fluorouridine to urokinase positive malignant cells in vitro.

  Bioorganic & medicinal chemistry letters 20100501

• Glycal formation in crystals of uridine phosphorylase.

  Biochemistry 20100427

• Chronic exposure of colorectal cancer cells in culture to fluoropyrimidine analogs induces thymidylate synthase and suppresses p53. A molecular explanation for the mechanism of 5-FU resistance.

  Anticancer research 20100401

• Bortezomib induces the formation of nuclear poly(A) RNA granules enriched in Sam68 and PABPN1 in sensory ganglia neurons.

  Neurotoxicity research 20100201

• In situ labeling of transcription sites in marine medaka.

  The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society 20100201

• Abdominal irradiation modulates 5-Fluorouracil pharmacokinetics.

  Journal of translational medicine 20100101

• Stable morphology, but dynamic internal reorganisation, of interphase human chromosomes in living cells.

  PloS one 20100101

• Active site conformational dynamics in human uridine phosphorylase 1.

  PloS one 20100101

• Phase I/II study of sequential therapy with irinotecan and S-1 for metastatic colorectal cancer.

  British journal of cancer 20091215

• TDP-43 localizes in mRNA transcription and processing sites in mammalian neurons.

  Journal of structural biology 20090901

• Structure of a functional ribonucleoprotein pseudouridine synthase bound to a substrate RNA.

  Nature structural & molecular biology 20090701

• Crystal structure of an RluF-RNA complex: a base-pair rearrangement is the key to selectivity of RluF for U2604 of the ribosome.

  Journal of molecular biology 20090515

• Epigenetic reversal of acquired resistance to 5-fluorouracil treatment.

  Molecular cancer therapeutics 20090501

• Decreased levels of UMP kinase as a mechanism of fluoropyrimidine resistance.

  Molecular cancer therapeutics 20090501

• Evidence for transcriptional activity in the syncytiotrophoblast of the human placenta.

  Placenta 20090401

• Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.

  Journal of medicinal chemistry 20090326

• Microsatellite instability in colorectal cancer and association with thymidylate synthase and dihydropyrimidine dehydrogenase expression.

  BMC cancer 20090101

• Mammalian MCM loading in late-G(1) coincides with Rb hyperphosphorylation and the transition to post-transcriptional control of progression into S-phase.

  PloS one 20090101

• Surface-enhanced Raman spectral measurements of 5-fluorouracil in saliva.

  Molecules (Basel, Switzerland) 20081022

• African swine fever virus protein p30 interaction with heterogeneous nuclear ribonucleoprotein K (hnRNP-K) during infection.

  FEBS letters 20081015

• Molecular characterization of a dual inhibitory and mutagenic activity of 5-fluorouridine triphosphate on viral RNA synthesis. Implications for lethal mutagenesis.

  Journal of molecular biology 20081010

• Concentrations of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine (FdCyd) and its cytotoxic metabolites in plasma of patients treated with FdCyd and tetrahydrouridine (THU).

  Cancer chemotherapy and pharmacology 20080701

• Intravesical treatments of bladder cancer: review.

  Pharmaceutical research 20080701

• Thymidylate synthase, thymidine phosphorylase and orotate phosphoribosyl transferase levels as predictive factors of chemotherapy in oral squamous cell carcinoma.

  Acta histochemica et cytochemica 20080627

• Bisphosphonate derivatives of nucleoside antimetabolites: hydrolytic stability and hydroxyapatite adsorption of 5'-beta,gamma-methylene and 5'-beta,gamma-(1-hydroxyethylidene) triphosphates of 5-fluorouridine and ara-cytidine.

  The Journal of organic chemistry 20080606

• Two distinct molecular mechanisms underlying cytarabine resistance in human leukemic cells.

  Cancer research 20080401

• Synthesis of chemically functionalized superparamagnetic nanoparticles as delivery vectors for chemotherapeutic drugs.

  Bioorganic & medicinal chemistry 20080315

• Efficacy of laser capture microdissection plus RT-PCR technique in analyzing gene expression levels in human gastric cancer and colon cancer.

  BMC cancer 20080101

• Suicide gene therapy with the yeast fusion gene cytosine deaminase/uracil phosphoribosyltransferase is not enough for pancreatic cancer.

  Pancreas 20071001

• A stochastic view of spliceosome assembly and recycling in the nucleus.

  PLoS computational biology 20071001

• Novel and highly regioselective route for synthesis of 5-fluorouridine lipophilic ester derivatives by lipozyme TL IM.

  Journal of biotechnology 20070510

• The Escherichia coli protein YjjG is a house-cleaning nucleotidase in vivo.

  FEMS microbiology letters 20070501

• Functional characterization of a gene encoding a dual domain for uridine kinase and uracil phosphoribosyltransferase in Arabidopsis thaliana.

  Plant molecular biology 20070301

• The fluorouridine insensitive 1 (fur1) mutant is defective in equilibrative nucleoside transporter 3 (ENT3), and thus represents an important pyrimidine nucleoside uptake system in Arabidopsis thaliana.

  The Plant journal : for cell and molecular biology 20070301

• Activity and substrate specificity of pyrimidine phosphorylases and their role in fluoropyrimidine sensitivity in colon cancer cell lines.

  The international journal of biochemistry & cell biology 20070101

• Biochemical purification of box H/ACA RNPs involved in pseudouridylation.

  Methods in enzymology 20070101

• Pharmacokinetics, metabolism, and oral bioavailability of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine in mice.

  Clinical cancer research : an official journal of the American Association for Cancer Research 20061215

• Controlled release of 5-fluorouridine from radiation-crosslinked poly(ethylene-co-vinyl acetate) films.

  Acta biomaterialia 20061101

• Mechanistic investigations of the pseudouridine synthase RluA using RNA containing 5-fluorouridine.

  Biochemistry 20061003

• The transcriptional regulator CBP has defined spatial associations within interphase nuclei.

  PLoS computational biology 20061001

• Evaluations of biomarkers associated with 5-FU sensitivity for non-small-cell lung cancer patients postoperatively treated with UFT.

  British journal of cancer 20060904

• Nuclear organization and dynamics of transcription sites in rat sensory ganglia neurons detected by incorporation of 5'-fluorouridine into nascent RNA.

  Neuroscience 20060630

• Identification of inhibitors of ribozyme self-cleavage in mammalian cells via high-throughput screening of chemical libraries.

  RNA (New York, N.Y.) 20060501

• Identification of AtENT3 as the main transporter for uridine uptake in Arabidopsis roots.

  Cell research 20060401

• 3D-QSAR studies on antitubercular thymidine monophosphate kinase inhibitors based on different alignment methods.

  Bioorganic & medicinal chemistry letters 20060215

• Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides.

  Bioorganic & medicinal chemistry 20051215

• Combined tumor therapy by using radiofrequency ablation and 5-FU-laden polymer implants: evaluation in rats and rabbits.

  Radiology 20051201

• Enhancement of the anti-tumor activity of S-1 by low-dose cisplatin in mice bearing the sarcoma-180 model.

  Anti-cancer drugs 20051101

• A low volume, high-throughput forward mutation assay in Salmonella typhimurium based on fluorouracil resistance.

  Mutation research 20051015

• Diverse gene expression pattern during 5-fluorouridine-induced apoptosis.

  International journal of oncology 20050801

• Enhancement of 5-fluorouracil sensitivity by an rTS signaling mimic in H630 colon cancer cells.

  Cancer research 20050701

• Prediction of genotoxicity of chemical compounds by statistical learning methods.

  Chemical research in toxicology 20050601

• The multidrug resistance protein 5 (ABCC5) confers resistance to 5-fluorouracil and transports its monophosphorylated metabolites.

  Molecular cancer therapeutics 20050501

• Light-induced reactions of Escherichia coli DNA photolyase monitored by Fourier transform infrared spectroscopy.

  The FEBS journal 20050401

• Synthesis and anti-viral activity of a series of d- and l-2'-deoxy-2'-fluororibonucleosides in the subgenomic HCV replicon system.

  Bioorganic & medicinal chemistry 20050301

• Effect of anticancer agents on codeinone-induced apoptosis in human cancer cell lines.

  Anticancer research 20050101

• The pseudouridine synthases: revisiting a mechanism that seemed settled.

  Journal of the American Chemical Society 20041013

• Upregulation of platelet derived endothelial cell growth factor/thymidine phosphorylase by interferon alpha.

  Nucleosides, nucleotides & nucleic acids 20041001

• Plasma concentrations of 5-fluorouracil and its metabolites in colon cancer patients.

  Pharmacological research 20040801

• Electrophysiological characterization of a recombinant human Na+-coupled nucleoside transporter (hCNT1) produced in Xenopus oocytes.

  The Journal of physiology 20040801

• Effects of oxaliplatin and CPT-11 on cytotoxicity and nucleic acid incorporation of the fluoropyrimidines.

  Journal of cancer research and clinical oncology 20040801

• Dihydropyrimidine dehydrogenase deficiency: impact of pharmacogenetics on 5-fluorouracil therapy.

  Clinical advances in hematology & oncology : H&O 20040801

• Modulation of thymidine phosphorylase by neoadjuvant chemotherapy in primary breast cancer.

  British journal of cancer 20040614

• Crystal structure to 1.7 a of the Escherichia coli pyrimidine nucleoside hydrolase YeiK, a novel candidate for cancer gene therapy.

  Structure (London, England : 1993) 20040501

• Nanoparticles with specific bioadhesive properties to circumvent the pre-systemic degradation of fluorinated pyrimidines.

  Journal of controlled release : official journal of the Controlled Release Society 20040416

• Pseudouridines in and near the branch site recognition region of U2 snRNA are required for snRNP biogenesis and pre-mRNA splicing in Xenopus oocytes.

  RNA (New York, N.Y.) 20040401

• Interactions of nucleoside analogs, caffeine, and nicotine with human concentrative nucleoside transporters 1 and 2 stably produced in a transport-defective human cell line.

  Molecular pharmacology 20040401

• Not all pseudouridine synthases are potently inhibited by RNA containing 5-fluorouridine.

  RNA (New York, N.Y.) 20040201

• Crystal structure and conformation of 5-fluorouridine: conformational preferences for 5-fluorinated pyranosides.

  Nucleosides, nucleotides & nucleic acids 20040101

• Both gene expression for orotate phosphoribosyltransferase and its ratio to dihydropyrimidine dehydrogenase influence outcome following fluoropyrimidine-based chemotherapy for metastatic colorectal cancer.

  British journal of cancer 20031020

• Comparison of HSV-1 thymidine kinase-dependent and -independent inhibition of replication-competent adenoviral vectors by a panel of drugs.

  Cancer gene therapy 20031001

• Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.

  Bioorganic & medicinal chemistry letters 20030915

• Identification of a novel human uridine phosphorylase.

  Biochemical and biophysical research communications 20030718

• [Purification and characterization of a uridine phosphorylase from Enterobacter aerogenes EAM-Z1].

  Wei sheng wu xue bao = Acta microbiologica Sinica 20030601

• Subconjunctival doxifluridine administration suppresses rat choroidal neovascularization through activated thymidine phosphorylase.

  Investigative ophthalmology & visual science 20030201

• Detection of thymidylate synthase modulators by a novel screening assay.

  Molecular pharmacology 20030101

• Enhanced drug-induced apoptosis associated with P-glycoprotein overexpression is specific to antimicrotubule agents.

  Pharmaceutical research 20030101

• An H/ACA guide RNA directs U2 pseudouridylation at two different sites in the branchpoint recognition region in Xenopus oocytes.

  RNA (New York, N.Y.) 20021201

• Potential applications of PLGA film-implants in modulating in vitro drugs release.

  International journal of pharmaceutics 20021106

• Simultaneous HPLC determination of 5-fluorouracil and its metabolites in plasma of cancer patients.

  Biomedical chromatography : BMC 20021001

• Identification of active antiviral compounds against a New York isolate of West Nile virus.

  Antiviral research 20020701

• The thermal stability of RNA duplexes containing modified base pairs placed at internal and terminal positions of the oligoribonucleotides.

  Biophysical chemistry 20020619

• RP-LC determination of 5-fluorouridine in nanoparticulate formulations.

  Journal of pharmaceutical and biomedical analysis 20020601

• In-vitro release of fluoropyrimidines from PLGA film implants.

  The Journal of pharmacy and pharmacology 20020601

• Uridine phosphorylase (-/-) murine embryonic stem cells clarify the key role of this enzyme in the regulation of the pyrimidine salvage pathway and in the activation of fluoropyrimidines.

  Cancer research 20020415

• [Studies on biotransformation of 5-FUR].

  Wei sheng wu xue bao = Acta microbiologica Sinica 20020201

• [Superselective arterial embolization for hemorrhage from malignant gestational trophoblastic tumor].

  Zhonghua fu chan ke za zhi 20020101

• Acquisition of human concentrative nucleoside transporter 2 (hcnt2) activity by gene transfer confers sensitivity to fluoropyrimidine nucleosides in drug-resistant leukemia cells.

  Molecular pharmacology 20011101

• Cloning and expression of uridine/cytidine kinase cDNA from human fibrosarcoma cells.

  International journal of molecular medicine 20010901

• Phosphorylation of uridine and cytidine nucleoside analogs by two human uridine-cytidine kinases.

  Molecular pharmacology 20010501

• Reduced cellular transport and activation of fluoropyrimidine nucleosides and resistance in human lymphocytic cell lines selected for arabinosylcytosine resistance.

  Biochemical pharmacology 20010101

• [Evaluation of intraperitoneal chemotherapy in stage IV gastrointestinal cancer].

  Zhonghua zhong liu za zhi [Chinese journal of oncology] 20010101

• Synthesis of rgd containing peptides. Comparative study of their incorporation to the surface of 5-fluoruridine loaded liposomes.

  Journal of liposome research 20010101

• Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds.

  Research in virology 19970101

• Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.

  Journal of medicinal chemistry 19860401