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88410-68-8 | 5'-Uridylic acid,2'-deoxy-5-fluoro-, homopolymer
CAS No: 88410-68-8 Catalog No: AG004HZK MDL No:
Product Description
Catalog Number:
AG004HZK
Chemical Name:
5'-Uridylic acid,2'-deoxy-5-fluoro-, homopolymer
CAS Number:
88410-68-8
Molecular Formula:
C9H12FN2O8P
Molecular Weight:
326.1723
IUPAC Name:
[(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
InChI:
InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
InChI Key:
HFEKDTCAMMOLQP-RRKCRQDMSA-N
SMILES:
O[C@H]1C[C@@H](O[C@@H]1COP(=O)(O)O)n1cc(F)c(=O)[nH]c1=O
UNII:
7CJ707H131
Properties
Complexity:
534
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
3
Defined Bond Stereocenter Count:
0
Exact Mass:
326.032g/mol
Formal Charge:
0
Heavy Atom Count:
21
Hydrogen Bond Acceptor Count:
9
Hydrogen Bond Donor Count:
4
Isotope Atom Count:
0
Molecular Weight:
326.173g/mol
Monoisotopic Mass:
326.032g/mol
Rotatable Bond Count:
4
Topological Polar Surface Area:
146A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-2.8
Literature
| Title | Journal |
|---|---|
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| Unique dual targeting of thymidylate synthase and topoisomerase1 by FdUMP[10] results in high efficacy against AML and low toxicity. | Blood 20120412 |
| Antifungal resistance and new strategies to control fungal infections. | International journal of microbiology 20120101 |
| A practical approach for assessing chemosensitivity in colorectal cancer cell lines by comparative analysis of cell viability and thymidylate synthase mRNA expression. | Journal of the Korean Surgical Society 20120101 |
| Aloe vera induced biomimetic assemblage of nucleobase into nanosized particles. | 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 |
| Quantitative and qualitative analysis of the antifungal activity of allicin alone and in combination with antifungal drugs. | PloS one 20120101 |
| Phosphoramidate ProTides of the anticancer agent FUDR successfully deliver the preformed bioactive monophosphate in cells and confer advantage over the parent nucleoside. | Journal of medicinal chemistry 20111027 |
| Calpain regulates thymidylate synthase-5-fluoro-dUMP complex levels associated with response to 5-fluorouracil in gastric cancer cells. | Cancer science 20110801 |
| Cellular pharmacology of multi- and duplex drugs consisting of ethynylcytidine and 5-fluoro-2'-deoxyuridine. | Investigational new drugs 20110401 |
| Structures of human thymidylate synthase R163K with dUMP, FdUMP and glutathione show asymmetric ligand binding. | Acta crystallographica. Section D, Biological crystallography 20110101 |
| Development of proteomics-based fungicides: new strategies for environmentally friendly control of fungal plant diseases. | International journal of molecular sciences 20110101 |
| Antifungal testing and high-throughput screening of compound library against Geomyces destructans, the etiologic agent of geomycosis (WNS) in bats. | PloS one 20110101 |
| Tegafur/gimeracil/oteracil (S-1) approved for the treatment of advanced gastric cancer in adults when given in combination with cisplatin: a review comparing it with other fluoropyrimidine-based therapies. | OncoTargets and therapy 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 |
| Genome-wide mRNA and microRNA profiling of the NCI 60 cell-line screen and comparison of FdUMP[10] with fluorouracil, floxuridine, and topoisomerase 1 poisons. | Molecular cancer therapeutics 20101201 |
| Electrochemistry and electrocatalytic of hemoglobin immobilized on FDU-15-Pt mesoporous materials. | Bioelectrochemistry (Amsterdam, Netherlands) 20101001 |
| Development and validation of a rapid and sensitive HPLC method for the quantification of 5-fluorocytosine and its metabolites. | Biomedical chromatography : BMC 20100501 |
| The role of thymidine phosphorylase in the induction of early growth response protein-1 and thrombospondin-1 by 5-fluorouracil in human cancer carcinoma cells. | International journal of oncology 20100501 |
| Design and characterization of a mutation outside the active site of human thymidylate synthase that affects ligand binding. | Protein engineering, design & selection : PEDS 20100201 |
| Differential expression of a novel gene BRE (TNFRSF1A modulator/BRCC45) in response to stress and biological signals. | Molecular biology reports 20100101 |
| CoFactor: Folate Requirement for Optimization of 5-Fluouracil Activity in Anticancer Chemotherapy. | Journal of oncology 20100101 |
| A case of hepatocellular carcinoma with pulmonary metastases treated successfully with a combination of repeated hepatic arterial infusion epirubicin and Cisplatin chemotherapy and systemic low-dose infusion of 5-Fluorouracil. | Gut and liver 20091201 |
| Simultaneous quantification of 5-FU, 5-FUrd, 5-FdUrd, 5-FdUMP, dUMP and TMP in cultured cell models by LC-MS/MS. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20091001 |
| Toxicity and efficacy of 5-fluorouracil and capecitabine in a patient with TYMS gene polymorphism: A challenge or a dilemma? | Clinical colorectal cancer 20091001 |
| 5-Fluorouracil and its active metabolite FdUMP cause DNA damage in human SW620 colon adenocarcinoma cell line. | Journal of applied toxicology : JAT 20090501 |
| Lapatinib, a dual EGFR and HER2 tyrosine kinase inhibitor, downregulates thymidylate synthase by inhibiting the nuclear translocation of EGFR and HER2. | PloS one 20090101 |
| Histopathological effects of cisplatin, doxorubicin and 5-flurouracil (5-FU) on the liver of male albino rats. | International journal of biological sciences 20090101 |
| Mechanisms of substrate selectivity for Bacillus anthracis thymidylate kinase. | Protein science : a publication of the Protein Society 20080901 |
| Interaction of nucleotide excision repair factors XPC-HR23B, XPA, and RPA with damaged DNA. | Biochemistry. Biokhimiia 20080801 |
| Chemical and genetic validation of dihydrofolate reductase-thymidylate synthase as a drug target in African trypanosomes. | Molecular microbiology 20080701 |
| A molecular modeling study of the interaction of 2'-fluoro-substituted analogues of dUMP/FdUMP with thymidylate synthase. | Bioorganic & medicinal chemistry letters 20080415 |
| Clonal population of flucytosine-resistant Candida tropicalis from blood cultures, Paris, France. | Emerging infectious diseases 20080401 |
| Synthesis of FUDP-N-acetylglucosamine and FUDP-glucose in Saccharomyces cerevisiae cells treated with 5-fluorouracil. | FEMS yeast research 20080301 |
| Probing the role of parasite-specific, distant structural regions on communication and catalysis in the bifunctional thymidylate synthase-dihydrofolate reductase from Plasmodium falciparum. | Biochemistry 20080205 |
| Synthesis, Spectroscopic, and Anticancerous Properties of Mixed Ligand Palladium(II) and Silver(I) Complexes with 4,6-Diamino-5-hydroxy-2-mercaptopyrimidine and 2,2'-Bipyridyl. | Metal-based drugs 20080101 |
| Efficacy of laser capture microdissection plus RT-PCR technique in analyzing gene expression levels in human gastric cancer and colon cancer. | BMC cancer 20080101 |
| Interactions of 2'-fluoro-substituted dUMP analogues with thymidylate synthase. | Biochemical and biophysical research communications 20071012 |
| Mechanisms of action of FdUMP[10]: metabolite activation and thymidylate synthase inhibition. | Oncology reports 20070701 |
| Phase-I trial of oral fluoropyrimidine anticancer agent (S-1) with concurrent radiotherapy in patients with unresectable pancreatic cancer. | British journal of cancer 20070507 |
| MRP8/ABCC11 directly confers resistance to 5-fluorouracil. | Molecular cancer therapeutics 20070101 |
| The complete genome sequence and analysis of the epsilonproteobacterium Arcobacter butzleri. | PloS one 20070101 |
| Capecitabine: an evidence-based review of its effectiveness in the treatment of carcinoma of the pancreas. | Core evidence 20070101 |
| Synergistic cytotoxic interaction in hormone-refractory prostate cancer with the triple combination docetaxel-erlotinib and 5-fluoro-5'-deoxyuridine. | Anti-cancer drugs 20060801 |
| In-vitro differential metabolism and activity of 5-fluorouracil between short-term, high-dose and long-term, low-dose treatments in human squamous carcinoma cells. | Anti-cancer drugs 20060401 |
| Sulfonyl-containing nucleoside phosphotriesters and phosphoramidates as novel anticancer prodrugs of 5-fluoro-2'-deoxyuridine 5'-monophosphate (FdUMP). | Molecular pharmaceutics 20060101 |
| Binding and repression of translation of the cognate mRNA by Trichinella spiralis thymidylate synthase differ from the corresponding interactions of the human enzyme. | The Biochemical journal 20050915 |
| A novel polypyrimidine antitumor agent FdUMP[10] induces thymineless death with topoisomerase I-DNA complexes. | Cancer research 20050601 |
| Synthesis and anticancer activities of amphiphilic 5-fluoro-2'-deoxyuridylic acid prodrugs. | European journal of medicinal chemistry 20050501 |
| The multidrug resistance protein 5 (ABCC5) confers resistance to 5-fluorouracil and transports its monophosphorylated metabolites. | Molecular cancer therapeutics 20050501 |
| Phosphorylation of Cytidine, Deoxycytidine, and Their Analog Monophosphates by Human UMP/CMP Kinase Is Differentially Regulated by ATP and Magnesium. | Molecular pharmacology 20050301 |
| Addition of 5-fluorouracil to doxorubicin-paclitaxel sequence increases caspase-dependent apoptosis in breast cancer cell lines. | Breast cancer research : BCR 20050101 |
| Synthesis of 5-ethynyl-2'-deoxyuridine-5'-boranomono phosphate as a potential thymidylate synthase inhibitor. | Nucleosides, nucleotides & nucleic acids 20050101 |
| The use of 19F spectroscopy and diffusion-weighted MRI to evaluate differences in gene-dependent enzyme prodrug therapies. | Molecular therapy : the journal of the American Society of Gene Therapy 20041101 |
| Thymidylate synthase predictive power is overcome by irinotecan combination therapy with S-1 for gastric cancer. | British journal of cancer 20041004 |
| A trojan horse approach for silencing thymidylate synthase. | Biochemistry 20040720 |
| A novel biweekly multidrug regimen of gemcitabine, oxaliplatin, 5-fluorouracil (5-FU), and folinic acid (FA) in pretreated patients with advanced colorectal carcinoma. | British journal of cancer 20040504 |
| Designing a pronucleotide stratagem: lessons from amino acid phosphoramidates of anticancer and antiviral pyrimidines. | Mini reviews in medicinal chemistry 20040501 |
| Enhanced DNA-directed effects of FdUMP[10] compared to 5FU. | Nucleosides, nucleotides & nucleic acids 20040101 |
| Subcutaneous interleukin-2, interferon alpha-2b and 5-fluorouracil in metastatic renal cell carcinoma as second-line treatment after failure of previous immunotherapy: a phase II trial. | British journal of cancer 20031215 |
| Relative free energies of binding to thymidylate synthase of 2- and/or 4-thio and/or 5-fluoro analogues of dUMP. | Journal of computer-aided molecular design 20031001 |
| Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase. | Bioorganic & medicinal chemistry letters 20030915 |
| Phase I/II study of daily carboplatin, 5-fluorouracil and concurrent radiation therapy for locally advanced non-small-cell lung cancer. | British journal of cancer 20030901 |
| Correlation between 5-fluorouracil metabolism and treatment response in two variants of C26 murine colon carcinoma. | British journal of cancer 20030818 |
| MRP8, ATP-binding cassette C11 (ABCC11), is a cyclic nucleotide efflux pump and a resistance factor for fluoropyrimidines 2',3'-dideoxycytidine and 9'-(2'-phosphonylmethoxyethyl)adenine. | The Journal of biological chemistry 20030808 |
| Probing electrostatic channeling in protozoal bifunctional thymidylate synthase-dihydrofolate reductase using site-directed mutagenesis. | The Journal of biological chemistry 20030801 |
| Chromosomal imbalances associated with acquired resistance to fluoropyrimidines in human colorectal cancer cells. | European journal of cancer (Oxford, England : 1990) 20030501 |
| Assessment of the effect of phosphorylated metabolites of anti-human immunodeficiency virus and anti-hepatitis B virus pyrimidine analogs on the behavior of human deoxycytidylate deaminase. | Molecular pharmacology 20030101 |
| Prediction of sensitivity to fluoropyrimidines by metabolic and target enzyme activities in gastric cancer. | Gastric cancer : official journal of the International Gastric Cancer Association and the Japanese Gastric Cancer Association 20030101 |
| Parenteral nutrition decreases hepatic dihydropyrimidine dehydrogenase activity and modulates catabolism of 5-fluorouracil in rats. | In vivo (Athens, Greece) 20030101 |
| Targeted molecular imaging. | Korean journal of radiology 20030101 |
| Gene therapy for intraperitoneally disseminated pancreatic cancers by Escherichia coli uracil phosphoribosiltransferase (UPRT) gene mediated by restricted replication-competent adenoviral vectors. | International journal of cancer 20021101 |
| Synthesis and evaluation of thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase. | Bioorganic & medicinal chemistry letters 20021007 |
| Gene therapy for pancreatic cancer targeting the genomic alterations of tumor suppressor genes using replication-selective oncolytic adenovirus. | Human cell 20020901 |
| Effects of antifolates on the binding of 5-fluoro-2'-deoxyuridine monophosphate to thymidylate synthase. | Biochemical pharmacology 20020815 |
| Efficacy and safety of FdUMP[10] in treatment of HT-29 human colon cancer xenografts. | International journal of oncology 20020801 |
| Cytotoxic targeting of F9 teratocarcinoma tumours with anti-ED-B fibronectin scFv antibody modified liposomes. | British journal of cancer 20020701 |
| Differences in natural ligand and fluoropyrimidine binding to human thymidylate synthase identified by transient-state spectroscopic and continuous variation methods. | Biochimica et biophysica acta 20020520 |
| Potentiation of the sensitivity of renal cell carcinoma cells to TRAIL-mediated apoptosis by subtoxic concentrations of 5-fluorouracil. | European journal of cancer (Oxford, England : 1990) 20020101 |
| Synthesis and enzymatic characterization of P1-thio-P2-oxo trideoxynucleoside diphosphates having AZT, FdU, or dT at the 3'-position. | Nucleosides, nucleotides & nucleic acids 20020101 |
| Roles of thymidylate synthase and dihydropyrimidine dehydrogenase in tumor progression and sensitivity to 5-fluorouracil in human gastric cancer. | Anticancer research 20020101 |
| Comparative antitumor activity of 5-fluorouracil and 5'-deoxy-5-fluorouridine in combination with interferon gamma in renal cell carcinoma cell lines. | Anticancer research 20020101 |
| Synthesis and biological studies of novel nucleoside phosphoramidate prodrugs. | Journal of medicinal chemistry 20011206 |
| In vitro generation of cytotoxic T lymphocytes against HLA-A2.1-restricted peptides derived from human thymidylate synthase. | Journal of chemotherapy (Florence, Italy) 20011001 |
| Targeted drug delivery to chemoresistant cells: folic acid derivatization of FdUMP[10] enhances cytotoxicity toward 5-FU-resistant human colorectal tumor cells. | The Journal of organic chemistry 20010824 |
| Determination of 5-fluorouracil and 5-fluoro-2'-deoxyuridine-5'-monophosphate in pancreatic cancer cell line and other biological materials using capillary electrophoresis. | Journal of chromatography. A 20010504 |
| Examination of the reduced affinity of the thymidylate synthase G52S mutation for FdUMP by ab initio and semi-empirical studies. | Molecular medicine (Cambridge, Mass.) 20010301 |
| Interleukin-2 and interleukin-4 increase the survival of retinal ganglion cells in culture. | Neuroreport 20010122 |
| Issues of normal tissue toxicity in patient and animal studies--effect of carbogen breathing in rats after 5-fluorouracil treatment. | Acta oncologica (Stockholm, Sweden) 20010101 |
| Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters. | Journal of medicinal chemistry 19860701 |
| Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates. | Journal of medicinal chemistry 19860401 |
| Mode of action of 5-fluorocytosine. | Biochemical pharmacology 19780301 |
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