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3690-10-6,MFCD04973699
Catalog No.:AA00C0UA

3690-10-6 | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

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1mg
98%
in stock  
$7.00   $5.00
- +
5mg
98%
in stock  
$11.00   $8.00
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10mg
98%
in stock  
$14.00   $10.00
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50mg
98%
in stock  
$23.00   $16.00
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100mg
98%
in stock  
$33.00   $23.00
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250mg
98%
in stock  
$44.00   $31.00
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1g
95%
in stock  
$137.00   $96.00
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5g
98%
in stock  
$316.00   $221.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00C0UA
Chemical Name:
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
CAS Number:
3690-10-6
Molecular Formula:
C9H12N2O5
Molecular Weight:
228.2020
MDL Number:
MFCD04973699
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cccnc1=O
Properties
Computed Properties
 
Complexity:
343  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
2  
XLogP3:
-1.5  

Literature

Title: DNA methyltransferase inhibitor zebularine inhibits human hepatic carcinoma cells proliferation and induces apoptosis.

Journal: PloS one 20130101

Title: Antileukemic activity of combined epigenetic agents, DNMT inhibitors zebularine and RG108 with HDAC inhibitors, against promyelocytic leukemia HL-60 cells.

Journal: Cellular & molecular biology letters 20121201

Title: Zebularine inhibits the growth of HeLa cervical cancer cells via cell cycle arrest and caspase-dependent apoptosis.

Journal: Molecular biology reports 20121001

Title: Flight of a cytidine deaminase complex with an imperfect transition state analogue inhibitor: mass spectrometric evidence for the presence of a trapped water molecule.

Journal: Biochemistry 20120814

Title: Epigenomic silencing of the BMP-4 gene in pituitary adenomas: a potential target for epidrug-induced re-expression.

Journal: Endocrinology 20120801

Title: Promoter methylation and tissue-specific transcription of the α7 nicotinic receptor gene, CHRNA7.

Journal: Journal of molecular neuroscience : MN 20120601

Title: An epigenetic mechanism for high, synergistic expression of indoleamine 2,3-dioxygenase 1 (IDO1) by combined treatment with zebularine and IFN-γ: potential therapeutic use in autoimmune diseases.

Journal: Molecular immunology 20120601

Title: The DNA methyltransferase inhibitors zebularine and decitabine induce mitochondria-mediated apoptosis and DNA damage in p53 mutant leukemic T cells.

Journal: International journal of cancer 20120301

Title: Light-regulated and cell-specific methylation of the maize PEPC promoter.

Journal: Journal of experimental botany 20120201

Title: DNA methyltransferase inhibitor, zebularine, delays tumor growth and induces apoptosis in a genetically engineered mouse model of breast cancer.

Journal: Molecular cancer therapeutics 20120201

Title: Mutations in epigenetic modifiers in myeloid malignancies and the prospect of novel epigenetic-targeted therapy.

Journal: Advances in hematology 20120101

Title: Epigenetic changes by zebularine leading to enhanced differentiation of human promyelocytic leukemia NB4 and KG1 cells.

Journal: Molecular and cellular biochemistry 20120101

Title: Effects of a novel DNA methyltransferase inhibitor Zebularine on human lens epithelial cells.

Journal: Molecular vision 20120101

Title: The expression of spinal methyl-CpG-binding protein 2, DNA methyltransferases and histone deacetylases is modulated in persistent pain states.

Journal: Molecular pain 20120101

Title: Epigenetic disregulation in oral cancer.

Journal: International journal of molecular sciences 20120101

Title: The influence of cis-regulatory elements on DNA methylation fidelity.

Journal: PloS one 20120101

Title: In planta assays involving epigenetically silenced genes reveal inhibition of cytosine methylation by genistein.

Journal: Plant methods 20120101

Title: DNMT (DNA methyltransferase) inhibitors radiosensitize human cancer cells by suppressing DNA repair activity.

Journal: Radiation oncology (London, England) 20120101

Title: Epigenetic effects of stress and corticosteroids in the brain.

Journal: Frontiers in cellular neuroscience 20120101

Title: RASSF1A and the Taxol Response in Ovarian Cancer.

Journal: Molecular biology international 20120101

Title: RASSF Signalling and DNA Damage: Monitoring the Integrity of the Genome?

Journal: Molecular biology international 20120101

Title: Epigenetic dysregulation in laryngeal squamous cell carcinoma.

Journal: Journal of oncology 20120101

Title: Epigenetics modifications and therapeutic prospects in human thyroid cancer.

Journal: Frontiers in endocrinology 20120101

Title: Transgenerational effects of stress exposure on offspring phenotypes in apomictic dandelion.

Journal: PloS one 20120101

Title: Combinatorial treatment of DNA and chromatin-modifying drugs cause cell death in human and canine osteosarcoma cell lines.

Journal: PloS one 20120101

Title: Cancer chemoprevention by targeting the epigenome.

Journal: Current drug targets 20111201

Title: Differential down-modulation of HLA class I and II molecule expression on human tumor cell lines upon in vivo transfer.

Journal: Cancer immunology, immunotherapy : CII 20111101

Title: Hypomethylating drugs efficiently decrease cytosine methylation in telomeric DNA and activate telomerase without affecting telomere lengths in tobacco cells.

Journal: Plant molecular biology 20111101

Title: Aberrant DNA methylation and prostate cancer.

Journal: Current genomics 20111101

Title: Genetic rearrangements can modify chromatin features at epialleles.

Journal: PLoS genetics 20111001

Title: Human hepatic cancer stem cells are characterized by common stemness traits and diverse oncogenic pathways.

Journal: Hepatology (Baltimore, Md.) 20110902

Title: The structural basis of RNA-catalyzed RNA polymerization.

Journal: Nature structural & molecular biology 20110901

Title: Epigenetic management of major psychosis.

Journal: Clinical epigenetics 20110801

Title: Evolutional and clinical implications of the epigenetic regulation of protein glycosylation.

Journal: Clinical epigenetics 20110801

Title: Insights into mutagenesis using Escherichia coli chromosomal lacZ strains that enable detection of a wide spectrum of mutational events.

Journal: Genetics 20110601

Title: 2´-deoxy-5,6-dihydro-5-azacytidine - a less toxic alternative of 2´-deoxy-5-azacytidine: a comparative study of hypomethylating potential.

Journal: Epigenetics 20110601

Title: 4-Pyridone-3-carboxamide-1-β-D-ribonucleoside triphosphate (4PyTP), a novel NAD metabolite accumulating in erythrocytes of uremic children: a biomarker for a toxic NAD analogue in other tissues?

Journal: Toxins 20110601

Title: Dynamic regulation of H3K27 trimethylation during Arabidopsis differentiation.

Journal: PLoS genetics 20110401

Title: MicroRNA let-7 suppresses nasopharyngeal carcinoma cells proliferation through downregulating c-Myc expression.

Journal: Journal of cancer research and clinical oncology 20110301

Title: Hypermethylation of specific microRNA genes in MLL-rearranged infant acute lymphoblastic leukemia: major matters at a micro scale.

Journal: Leukemia 20110301

Title: New nucleoside analogs for patients with hematological malignancies.

Journal: Expert opinion on investigational drugs 20110301

Title: Reversal of endogenous dopamine receptor silencing in pituitary cells augments receptor-mediated apoptosis.

Journal: Endocrinology 20110201

Title: A novel epigenetic phenotype associated with the most aggressive pathway of bladder tumor progression.

Journal: Journal of the National Cancer Institute 20110105

Title: Effectively incorporating selected multimedia content into medical publications.

Journal: BMC medicine 20110101

Title: Uracil DNA N-glycosylase promotes assembly of human centromere protein A.

Journal: PloS one 20110101

Title: Continuous and low-energy 125I seed irradiation changes DNA methyltransferases expression patterns and inhibits pancreatic cancer tumor growth.

Journal: Journal of experimental & clinical cancer research : CR 20110101

Title: Epigenetic regulation of cancer-associated genes in ovarian cancer.

Journal: International journal of molecular sciences 20110101

Title: 5-azacytidine in chronic myelomonocytic leukemia: case report and review of literature.

Journal: Mediterranean journal of hematology and infectious diseases 20110101

Title: Myelodysplastic syndrome and histone deacetylase inhibitors: 'to be or not to be acetylated'?

Journal: Journal of biomedicine & biotechnology 20110101

Title: Epigenetic therapy for breast cancer.

Journal: International journal of molecular sciences 20110101

Title: Generation of reactive oxygen species during apoptosis induced by DNA-damaging agents and/or histone deacetylase inhibitors.

Journal: Oxidative medicine and cellular longevity 20110101

Title: GSTP1 DNA methylation and expression status is indicative of 5-aza-2'-deoxycytidine efficacy in human prostate cancer cells.

Journal: PloS one 20110101

Title: Zebularine suppresses TGF-beta-induced lens epithelial cell-myofibroblast transdifferentiation by inhibiting MeCP2.

Journal: Molecular vision 20110101

Title: Cigarette smoking and p16INK4α gene promoter hypermethylation in non-small cell lung carcinoma patients: a meta-analysis.

Journal: PloS one 20110101

Title: Epigenomics of ovarian cancer and its chemoprevention.

Journal: Frontiers in genetics 20110101

Title: Cytosine methyltransferases as tumor markers.

Journal: Current genomics 20101201

Title: Measuring topology of low-intensity DNA methylation sites for high-throughput assessment of epigenetic drug-induced effects in cancer cells.

Journal: Experimental cell research 20101115

Title: DNA methylation regulates cocaine-induced behavioral sensitization in mice.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20101101

Title: Hypermethylation of PTGER2 confers prostaglandin E2 resistance in fibrotic fibroblasts from humans and mice.

Journal: The American journal of pathology 20101101

Title: An integrated genomic and epigenomic approach predicts therapeutic response to zebularine in human liver cancer.

Journal: Science translational medicine 20101020

Title: Enhanced growth inhibition by combined DNA methylation/HDAC inhibitors in lung tumor cells with silenced CDKN2A.

Journal: International journal of oncology 20101001

Title: The effect of epigenetic regulation of fucosylation on TRAIL-induced apoptosis.

Journal: Glycoconjugate journal 20101001

Title: Determination of hypersensitivity to genotoxic agents among Escherichia coli single gene knockout mutants.

Journal: DNA repair 20100904

Title: Inhibition of murine DNA methyltransferase Dnmt3a by DNA duplexes containing pyrimidine-2(1H)-one.

Journal: Biochemistry. Biokhimiia 20100901

Title: Clinical advances in hypomethylating agents targeting epigenetic pathways.

Journal: Current cancer drug targets 20100801

Title: Scaling laws for plasma concentrations and tolerable doses of anticancer drugs.

Journal: Cancer research 20100615

Title: Effects of a novel DNA methyltransferase inhibitor zebularine on human breast cancer cells.

Journal: Breast cancer research and treatment 20100401

Title: CpG island methylation affects accessibility of the proximal BRCA1 promoter to transcription factors.

Journal: Breast cancer research and treatment 20100401

Title: Epigenetic approaches to psychiatric disorders.

Journal: Dialogues in clinical neuroscience 20100301

Title: Use of Drosophila deoxynucleoside kinase to study mechanism of toxicity and mutagenicity of deoxycytidine analogs in Escherichia coli.

Journal: DNA repair 20100204

Title: The liver X-receptor gene promoter is hypermethylated in a mouse model of prenatal protein restriction.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20100201

Title: DNA-dependent protein kinase (DNA-PK)-deficient human glioblastoma cells are preferentially sensitized by Zebularine.

Journal: Carcinogenesis 20100201

Title: Cooperation of multiple chromatin modifications can generate unanticipated stability of epigenetic States in Arabidopsis.

Journal: The Plant cell 20100101

Title: A comparison of azacitidine and decitabine activities in acute myeloid leukemia cell lines.

Journal: PloS one 20100101

Title: Transgenerational adaptation of Arabidopsis to stress requires DNA methylation and the function of Dicer-like proteins.

Journal: PloS one 20100101

Title: Epigenetics of human cutaneous melanoma: setting the stage for new therapeutic strategies.

Journal: Journal of translational medicine 20100101

Title: Demethylation by 5-aza-2'-deoxycytidine in colorectal cancer cells targets genomic DNA whilst promoter CpG island methylation persists.

Journal: BMC cancer 20100101

Title: Oxidative stress and DNA methylation in prostate cancer.

Journal: Obstetrics and gynecology international 20100101

Title: Mechanistic insights on the inhibition of c5 DNA methyltransferases by zebularine.

Journal: PloS one 20100101

Title: Equitoxic doses of 5-azacytidine and 5-aza-2'deoxycytidine induce diverse immediate and overlapping heritable changes in the transcriptome.

Journal: PloS one 20100101

Title: Epigenetic control of estrogen receptor expression and tumor suppressor genes is modulated by bioactive food compounds.

Journal: Annals of nutrition & metabolism 20100101

Title: Biological rationale for the use of DNA methyltransferase inhibitors as new strategy for modulation of tumor response to chemotherapy and radiation.

Journal: Molecular cancer 20100101

Title: Specific promoter methylation identifies different subgroups of MLL-rearranged infant acute lymphoblastic leukemia, influences clinical outcome, and provides therapeutic options.

Journal: Blood 20091224

Title: Chemotherapeutic drug-induced ABCG2 promoter demethylation as a novel mechanism of acquired multidrug resistance.

Journal: Neoplasia (New York, N.Y.) 20091201

Title: Profiling the repertoire of phenotypes influenced by environmental cues that occur during asexual reproduction.

Journal: Genome research 20091101

Title: DNA (Cytosine-C5) methyltransferase inhibition by oligodeoxyribonucleotides containing 2-(1H)-pyrimidinone (zebularine aglycon) at the enzymatic target site.

Journal: Biochemical pharmacology 20090915

Title: Synthesis and conformational analysis of locked carbocyclic analogues of 1,3-diazepinone riboside, a high-affinity cytidine deaminase inhibitor.

Journal: The Journal of organic chemistry 20090821

Title: Methylation of zebularine: a quantum mechanical study incorporating interactive 3D pdf graphs.

Journal: The journal of physical chemistry. B 20090820

Title: CpG methylation controls reactivation of HIV from latency.

Journal: PLoS pathogens 20090801

Title: Potential of DNMT and its Epigenetic Regulation for Lung Cancer Therapy.

Journal: Current genomics 20090801

Title: Zebularine suppresses the apoptotic potential of 5-fluorouracil via cAMP/PKA/CREB pathway against human oral squamous cell carcinoma cells.

Journal: Cancer chemotherapy and pharmacology 20090701

Title: The DNA methyltransferase inhibitors azacitidine, decitabine and zebularine exert differential effects on cancer gene expression in acute myeloid leukemia cells.

Journal: Leukemia 20090601

Title: Lasting epigenetic influence of early-life adversity on the BDNF gene.

Journal: Biological psychiatry 20090501

Title: [Recent advances in DNA demethylation in tumor therapy].

Journal: Zhonghua bing li xue za zhi = Chinese journal of pathology 20090501

Title: Epigenetic regulation of human buccal mucosa mitochondrial superoxide dismutase gene expression by diet.

Journal: The British journal of nutrition 20090301

Title: Inhibition of cytidine deaminase by zebularine enhances the antineoplastic action of 5-aza-2'-deoxycytidine.

Journal: Cancer chemotherapy and pharmacology 20090201

Title: Effective, homogeneous and transient interference with cytosine methylation in plant genomic DNA by zebularine.

Journal: The Plant journal : for cell and molecular biology 20090201

Title: Survival motor neuron gene 2 silencing by DNA methylation correlates with spinal muscular atrophy disease severity and can be bypassed by histone deacetylase inhibition.

Journal: Human molecular genetics 20090115

Title: Transgenerational stress memory is not a general response in Arabidopsis.

Journal: PloS one 20090101

Title: Decytabine enhances cytotoxicity induced by oxaliplatin and 5-fluorouracil in the colorectal cancer cell line Colo-205.

Journal: Cancer cell international 20090101

Title: The combination effect of sodium butyrate and 5-Aza-2'-deoxycytidine on radiosensitivity in RKO colorectal cancer and MCF-7 breast cancer cell lines.

Journal: World journal of surgical oncology 20090101

Title: Integrated analysis of DNA methylation and gene expression reveals specific signaling pathways associated with platinum resistance in ovarian cancer.

Journal: BMC medical genomics 20090101

Title: Molecular control of HIV-1 postintegration latency: implications for the development of new therapeutic strategies.

Journal: Retrovirology 20090101

Title: Activation of p16 gene silenced by DNA methylation in cancer cells by phosphoramidate derivatives of 2'-deoxyzebularine.

Journal: Journal of medicinal chemistry 20081211

Title: p53-inducible ribonucleotide reductase (p53R2/RRM2B) is a DNA hypomethylation-independent decitabine gene target that correlates with clinical response in myelodysplastic syndrome/acute myelogenous leukemia.

Journal: Cancer research 20081115

Title: Epigenetic regulation of BDNF gene transcription in the consolidation of fear memory.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20081015

Title: Cancer prevention: epigenetics steps up to the plate.

Journal: Cancer prevention research (Philadelphia, Pa.) 20080901

Title: Long-term epigenetic therapy with oral zebularine has minimal side effects and prevents intestinal tumors in mice.

Journal: Cancer prevention research (Philadelphia, Pa.) 20080901

Title: Effects of green tea polyphenol on methylation status of RECK gene and cancer cell invasion in oral squamous cell carcinoma cells.

Journal: British journal of cancer 20080819

Title: Epigenetic treatment of myelodysplastic syndromes and acute myeloid leukemias.

Journal: Current medicinal chemistry 20080601

Title: Promoter analysis of epigenetically controlled genes in bladder cancer.

Journal: Genes, chromosomes & cancer 20080501

Title: The role of DNA hypermethylation and demethylation in cancer and cancer therapy.

Journal: Current oncology (Toronto, Ont.) 20080401

Title: Incorporation of zebularine from its 2'-deoxyribonucleoside triphosphate derivative and activity as a template-coding nucleobase.

Journal: Nucleosides, nucleotides & nucleic acids 20080201

Title: DNA methylation inhibitor 5-Aza-2'-deoxycytidine induces reversible genome-wide DNA damage that is distinctly influenced by DNA methyltransferases 1 and 3B.

Journal: Molecular and cellular biology 20080101

Title: Importance of dose-schedule of 5-aza-2'-deoxycytidine for epigenetic therapy of cancer.

Journal: BMC cancer 20080101

Title: The epigenetics of cancer in children.

Journal: Klinische Padiatrie 20080101

Title: Ovarian cancer plasticity and epigenomics in the acquisition of a stem-like phenotype.

Journal: Journal of ovarian research 20080101

Title: Zebularine-induced reduction in VEGF secretion by HIF-1α degradation in oral squamous cell carcinoma.

Journal: Molecular medicine reports 20080101

Title: Inhibition of DNA methylation is involved in transdifferentiation of myoblasts into smooth muscle cells.

Journal: Molecules and cells 20071231

Title: Epigenetic regulation of chemosensitivity to 5-fluorouracil and cisplatin by zebularine in oral squamous cell carcinoma.

Journal: International journal of oncology 20071201

Title: Targeted therapies in the management of metastatic bladder cancer.

Journal: Biologics : targets & therapy 20071201

Title: Low dose Zebularine treatment enhances immunogenicity of tumor cells.

Journal: Cancer letters 20071108

Title: Molecular consequences of SOD2 expression in epigenetically silenced pancreatic carcinoma cell lines.

Journal: British journal of cancer 20071022

Title: AKAP12, a gene with tumour suppressor properties, is a target of promoter DNA methylation in childhood myeloid malignancies.

Journal: British journal of haematology 20070901

Title: The Ras-association domain family (RASSF) members and their role in human tumourigenesis.

Journal: Biochimica et biophysica acta 20070901

Title: DNA methyltransferase inhibitors coordinately induce expression of the human reelin and glutamic acid decarboxylase 67 genes.

Journal: Molecular pharmacology 20070301

Title: Zebularine inhibits human acute myeloid leukemia cell growth in vitro in association with p15INK4B demethylation and reexpression.

Journal: Experimental hematology 20070201

Title: Apoptosis, proliferation and differentiation patterns are influenced by Zebularine and SAHA in pancreatic cancer models.

Journal: Scandinavian journal of gastroenterology 20070101

Title: Zebularine reactivates silenced E-cadherin but unlike 5-Azacytidine does not induce switching from latent to lytic Epstein-Barr virus infection in Burkitt's lymphoma Akata cells.

Journal: Molecular cancer 20070101

Title: Nidogen 1 and 2 gene promoters are aberrantly methylated in human gastrointestinal cancer.

Journal: Molecular cancer 20070101

Title: Clinical implications and utility of field cancerization.

Journal: Cancer cell international 20070101

Title: Methylation of tumour suppressor genes APAF-1 and DAPK-1 and in vitro effects of demethylating agents in bladder and kidney cancer.

Journal: British journal of cancer 20061218

Title: Epigenetic regulation of tumor endothelial cell anergy: silencing of intercellular adhesion molecule-1 by histone modifications.

Journal: Cancer research 20061115

Title: A mass balance and disposition study of the DNA methyltransferase inhibitor zebularine (NSC 309132) and three of its metabolites in mice.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20061001

Title: Reversal of p53 epigenetic silencing in multiple myeloma permits apoptosis by a p53 activator.

Journal: Cancer biology & therapy 20060901

Title: Reactivation of p53 function with a demethylating agent.

Journal: Cancer biology & therapy 20060901

Title: DNA damage-induced down-regulation of human Cdc25C and Cdc2 is mediated by cooperation between p53 and maintenance DNA (cytosine-5) methyltransferase 1.

Journal: The Journal of biological chemistry 20060825

Title: p53 expression after treatment with zebularine is not due to demethylation.

Journal: Cancer research 20060701

Title: Evidence that DNA (cytosine-5) methyltransferase regulates synaptic plasticity in the hippocampus.

Journal: The Journal of biological chemistry 20060609

Title: Methylation of the ASC gene promoter is associated with aggressive prostate cancer.

Journal: The Prostate 20060515

Title: Transcriptional silencing of multiple genes in trophozoites of Entamoeba histolytica.

Journal: PLoS pathogens 20060501

Title: The role of DNA hypomethylation in the control of stromelysin gene expression.

Journal: Biochemical and biophysical research communications 20060421

Title: Ubiquitous activation of Ras and Jak/Stat pathways in human HCC.

Journal: Gastroenterology 20060401

Title: Functional diversity of DNA methyltransferase inhibitors in human cancer cell lines.

Journal: Cancer research 20060301

Title: Quantitative determination of zebularine (NSC 309132), a DNA methyltransferase inhibitor, and three metabolites in murine plasma by high-performance liquid chromatography coupled with on-line radioactivity detection.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060202

Title: The novel DNA methylation inhibitor zebularine is effective against the development of murine T-cell lymphoma.

Journal: Blood 20060201

Title: Angiostatic activity of DNA methyltransferase inhibitors.

Journal: Molecular cancer therapeutics 20060201

Title: Epigenetics provides a new generation of oncogenes and tumour-suppressor genes.

Journal: British journal of cancer 20060130

Title: Zebularine metabolism by aldehyde oxidase in hepatic cytosol from humans, monkeys, dogs, rats, and mice: influence of sex and inhibitors.

Journal: Bioorganic & medicinal chemistry 20060101

Title: Antineoplastic effects of the DNA methylation inhibitor hydralazine and the histone deacetylase inhibitor valproic acid in cancer cell lines.

Journal: Cancer cell international 20060101

Title: Hydralazine target: from blood vessels to the epigenome.

Journal: Journal of translational medicine 20060101

Title: Zebularine: a unique molecule for an epigenetically based strategy in cancer chemotherapy.

Journal: Annals of the New York Academy of Sciences 20051101

Title: Antimitogenic and chemosensitizing effects of the methylation inhibitor zebularine in ovarian cancer.

Journal: Molecular cancer therapeutics 20051001

Title: Comparison of biological effects of non-nucleoside DNA methylation inhibitors versus 5-aza-2'-deoxycytidine.

Journal: Molecular cancer therapeutics 20051001

Title: Xenopus CENP-A assembly into chromatin requires base excision repair proteins.

Journal: DNA repair 20050712

Title: Metabolic activation of zebularine, a novel DNA methylation inhibitor, in human bladder carcinoma cells.

Journal: Biochemical pharmacology 20050701

Title: Enhancement of in vitro and in vivo tumor cell radiosensitivity by the DNA methylation inhibitor zebularine.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050615

Title: RNA editing produces glycine receptor alpha3(P185L), resulting in high agonist potency.

Journal: Nature neuroscience 20050601

Title: Interleukin 6 supports the maintenance of p53 tumor suppressor gene promoter methylation.

Journal: Cancer research 20050601

Title: Plasma pharmacokinetics, oral bioavailability, and interspecies scaling of the DNA methyltransferase inhibitor, zebularine.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050515

Title: Epigenetic silencing of manganese superoxide dismutase (SOD-2) in KAS 6/1 human multiple myeloma cells increases cell proliferation.

Journal: Cancer biology & therapy 20050501

Title: Functional characterization of novel human and mouse equilibrative nucleoside transporters (hENT3 and mENT3) located in intracellular membranes.

Journal: The Journal of biological chemistry 20050422

Title: Cancer epigenetics.

Journal: Human molecular genetics 20050415

Title: Origin of tight binding of a near-perfect transition-state analogue by cytidine deaminase: implications for enzyme catalysis.

Journal: Journal of the American Chemical Society 20050309

Title: Enhancement of antineoplastic action of 5-aza-2'-deoxycytidine by zebularine on L1210 leukemia.

Journal: Anti-cancer drugs 20050301

Title: Epigenetic silencing of the human nucleotide excision repair gene, hHR23B, in interleukin-6-responsive multiple myeloma KAS-6/1 cells.

Journal: The Journal of biological chemistry 20050211

Title: Structure of human cytidine deaminase bound to a potent inhibitor.

Journal: Journal of medicinal chemistry 20050210

Title: DNA methylation and cancer therapy: new developments and expectations.

Journal: Current opinion in oncology 20050101

Title: Zebularine: a unique molecule for an epigenetically based strategy in cancer chemotherapy. The magic of its chemistry and biology.

Journal: Nucleosides, nucleotides & nucleic acids 20050101

Title: Epigenetics of cervical cancer. An overview and therapeutic perspectives.

Journal: Molecular cancer 20050101

Title: Zebularine: a new drug for epigenetic therapy.

Journal: Biochemical Society transactions 20041201

Title: Three-dimensional structure of the R115E mutant of T4-bacteriophage 2'-deoxycytidylate deaminase.

Journal: Biochemistry 20041102

Title: Zebularine: a candidate for epigenetic cancer therapy.

Journal: Drug discovery today 20041101

Title: The in vitro and in vivo effects of re-expressing methylated von Hippel-Lindau tumor suppressor gene in clear cell renal carcinoma with 5-aza-2'-deoxycytidine.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20041015

Title: Preferential response of cancer cells to zebularine.

Journal: Cancer cell 20040801

Title: Scientists probe shutting down cancer cells by awakening silenced genes.

Journal: JAMA 20040519

Title: Microarray analysis of epigenetic silencing of gene expression in the KAS-6/1 multiple myeloma cell line.

Journal: Cancer research 20040515

Title: Mutagenicity of the cytidine analog zebularine in Escherichia coli.

Journal: DNA repair 20040203

Title: Synthesis, stability, and protonation studies of a self-complementary dodecamer containing the modified nucleoside 2'-deoxyzebularine.

Journal: Biopolymers 20040101

Title: Potent inhibition of HhaI DNA methylase by the aglycon of 2-(1H)-pyrimidinone riboside (zebularine) at the GCGC recognition domain.

Journal: Annals of the New York Academy of Sciences 20031201

Title: Use of nucleotide analogs by class I and class II CCA-adding enzymes (tRNA nucleotidyltransferase): deciphering the basis for nucleotide selection.

Journal: RNA (New York, N.Y.) 20030801

Title: Human cytomegalovirus requires cellular deoxycytidylate deaminase for replication in quiescent cells.

Journal: The Journal of general virology 20030601

Title: Drug reactivates genes to inhibit cancer.

Journal: Drug discovery today 20030515

Title: Inhibition of DNA methylation and reactivation of silenced genes by zebularine.

Journal: Journal of the National Cancer Institute 20030305

Title: Zebularine: a novel DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases.

Journal: Journal of molecular biology 20020823

Title: Enzymatic conformational fluctuations along the reaction coordinate of cytidine deaminase.

Journal: Protein science : a publication of the Protein Society 20020601

Title: 93rd Annual Meeting of the American Association for Cancer Research, San Francisco, CA, USA, 6-10 April 2002.

Journal: Breast cancer research : BCR 20020101

Title: Champion C, et al. Mechanistic insights on the inhibition of c5 DNA methyltransferases by zebularine. PLoS One. 2010 Aug 24;5(8):e12388.

Title: Cheng JC, et al. Inhibition of DNA methylation and reactivation of silenced genes by zebularine. J Natl Cancer Inst. 2003 Mar 5;95(5):399-409.

Title: Billam M, et al. Effects of a novel DNA methyltransferase inhibitor zebularine on human breast cancer cells. Breast Cancer Res Treat. 2010 Apr;120(3):581-92.

Title: Lemaire M, et al. Inhibition of cytidine deaminase by zebularine enhances the antineoplastic action of 5-aza-2'-deoxycytidine. Cancer Chemother Pharmacol. 2009 Feb;63(3):411-6.

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Tags:3690-10-6 Molecular Formula|3690-10-6 MDL|3690-10-6 SMILES|3690-10-6 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one