2140-61-6 | 5-Methylcytidine

Packsize	Purity	Availability	Price	Discounted Price
250mg	97%	in stock	$13.00	$9.00
1g	97%	in stock	$23.00	$16.00
5g	97%	in stock	$88.00	$61.00
10g	97%	in stock	$166.00	$116.00
25g	97%	in stock	$362.00	$253.00
100g	97%	in stock	$1,317.00	$922.00

Description

• Catalog Number: AB45341
• Chemical Name: 5-Methylcytidine
• CAS Number: 2140-61-6
• Molecular Formula: C10H15N3O5
• Molecular Weight: 257.2432
• MDL Number: MFCD00006548
• SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cc(C)c(nc1=O)N

Computed Properties

• Complexity: 422
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 4
• Heavy Atom Count: 18
• Hydrogen Bond Acceptor Count: 5
• Hydrogen Bond Donor Count: 4
• Rotatable Bond Count: 2
• XLogP3: -2

Literature

• DNA methylation program in developing hippocampus and its alteration by alcohol.

  PloS one 20130101

• Contribution of AT-, GC-, and methylated cytidine-rich DNA to chromatin composition in Malpighian tubule cell nuclei of Panstrongylus megistus (Hemiptera, Reduviidae).

  Acta histochemica 20121101

• Maf1-mediated repression of RNA polymerase III transcription inhibits tRNA degradation via RTD pathway.

  RNA (New York, N.Y.) 20121001

• Prevention of age-related changes in hippocampal levels of 5-methylcytidine by caloric restriction.

  Neurobiology of aging 20120801

• Age-related increase in levels of 5-hydroxymethylcytosine in mouse hippocampus is prevented by caloric restriction.

  Current Alzheimer research 20120601

• Increased erythropoiesis in mice injected with submicrogram quantities of pseudouridine-containing mRNA encoding erythropoietin.

  Molecular therapy : the journal of the American Society of Gene Therapy 20120501

• Alteration of DNA demethylation dynamics by in vitro culture conditions in rabbit pre-implantation embryos.

  Epigenetics 20120501

• In Posidonia oceanica cadmium induces changes in DNA methylation and chromatin patterning.

  Journal of experimental botany 20120101

• Dynamic DNA cytosine methylation in the Populus trichocarpa genome: tissue-level variation and relationship to gene expression.

  BMC genomics 20120101

• High resolution methylome map of rat indicates role of intragenic DNA methylation in identification of coding region.

  PloS one 20120101

• Tet2 disruption leads to enhanced self-renewal and altered differentiation of fetal liver hematopoietic stem cells.

  Scientific reports 20120101

• A cross-platform genome-wide comparison of the relationship of promoter DNA methylation to gene expression.

  Frontiers in genetics 20120101

• Transgenerational actions of environmental compounds on reproductive disease and identification of epigenetic biomarkers of ancestral exposures.

  PloS one 20120101

• An unexpected function of the Prader-Willi syndrome imprinting center in maternal imprinting in mice.

  PloS one 20120101

• Global methylation patterns in idiopathic pulmonary fibrosis.

  PloS one 20120101

• Breast cancer cells induce stromal fibroblasts to secrete ADAMTS1 for cancer invasion through an epigenetic change.

  PloS one 20120101

• Analysis of the methylome of human embryonic stem cells employing methylated DNA immunoprecipitation coupled to next-generation sequencing.

  Methods in molecular biology (Clifton, N.J.) 20120101

• Environmentally induced epigenetic transgenerational inheritance of ovarian disease.

  PloS one 20120101

• 5-Methylcytosine and 5-hydroxymethylcytosine spatiotemporal profiles in the mouse zygote.

  PloS one 20120101

• Methylated DNA immunoprecipitation (MeDIP) from low amounts of cells.

  Methods in molecular biology (Clifton, N.J.) 20120101

• The RNA-methyltransferase Misu (NSun2) poises epidermal stem cells to differentiate.

  PLoS genetics 20111201

• Neonatal exposure to high doses of 17β-estradiol results in inhibition of heparanase-1 expression in the adult prostate.

  Histochemistry and cell biology 20111101

• Selective derivatization of cytosine and methylcytosine moieties with 2-bromoacetophenone for submicrogram DNA methylation analysis by reversed phase HPLC with spectrofluorimetric detection.

  Analytical chemistry 20111015

• The state-of-the-art determination of urinary nucleosides using chromatographic techniques 'hyphenated' with advanced bioinformatic methods.

  Analytical and bioanalytical chemistry 20111001

• Retrotransposon-induced heterochromatin spreading in the mouse revealed by insertional polymorphisms.

  PLoS genetics 20110901

• Epigenetic effect of cadmium on global de novo DNA hypomethylation in the cadmium-induced ventral body wall defect (VBWD) in the chick model.

  Toxicological sciences : an official journal of the Society of Toxicology 20110401

• Arabidopsis HDA6 regulates locus-directed heterochromatin silencing in cooperation with MET1.

  PLoS genetics 20110401

• Phenobarbital mediates an epigenetic switch at the constitutive androstane receptor (CAR) target gene Cyp2b10 in the liver of B6C3F1 mice.

  PloS one 20110101

• Transformation of human mesenchymal cells and skin fibroblasts into hematopoietic cells.

  PloS one 20110101

• Energy metabolism in H460 lung cancer cells: effects of histone deacetylase inhibitors.

  PloS one 20110101

• MiR-185 targets the DNA methyltransferases 1 and regulates global DNA methylation in human glioma.

  Molecular cancer 20110101

• Retroviral integration mutagenesis in mice and comparative analysis in human AML identify reduced PTP4A3 expression as a prognostic indicator.

  PloS one 20110101

• Epigenetic modulation of miR-122 facilitates human embryonic stem cell self-renewal and hepatocellular carcinoma proliferation.

  PloS one 20110101

• Structure of an archaeal homologue of the bacterial Fmu/RsmB/RrmB rRNA cytosine 5-methyltransferase.

  Acta crystallographica. Section D, Biological crystallography 20101201

• A quantitative systems approach reveals dynamic control of tRNA modifications during cellular stress.

  PLoS genetics 20101201

• Label-free DNA methylation analysis using opto-fluidic ring resonators.

  Biosensors & bioelectronics 20101115

• AutoMeDIP-seq: a high-throughput, whole genome, DNA methylation assay.

  Methods (San Diego, Calif.) 20101101

• Nanomechanical recognition measurements of individual DNA molecules reveal epigenetic methylation patterns.

  Nature nanotechnology 20101101

• Crystal structure of Methanocaldococcus jannaschii Trm4 complexed with sinefungin.

  Journal of molecular biology 20100820

• Multi-site-specific 16S rRNA methyltransferase RsmF from Thermus thermophilus.

  RNA (New York, N.Y.) 20100801

• Ribonucleoside labeling with Os(VI): a methodological approach to evaluation of RNA methylation by HPLC-ICP-MS.

  Metallomics : integrated biometal science 20100201

• Genome-wide DNA methylation profiling reveals novel epigenetically regulated genes and non-coding RNAs in human testicular cancer.

  British journal of cancer 20100119

• Generation of a recombinant single-chain variable fragment (scFv) targeting 5-methyl-2'-deoxycytidine.

  Journal of biochemistry 20100101

• Altered intra-nuclear organisation of heterochromatin and genes in ICF syndrome.

  PloS one 20100101

• Trichostatin A and 5-azacytidine both cause an increase in global histone H4 acetylation and a decrease in global DNA and H3K9 methylation during mitosis in maize.

  BMC plant biology 20100101

• Transfer RNA modifications and genes for modifying enzymes in Arabidopsis thaliana.

  BMC plant biology 20100101

• Assessing the efficiency and significance of Methylated DNA Immunoprecipitation (MeDIP) assays in using in vitro methylated genomic DNA.

  BMC research notes 20100101

• Epigenetic transgenerational actions of vinclozolin on promoter regions of the sperm epigenome.

  PloS one 20100101

• Transcriptome, methylome and genomic variations analysis of ectopic thyroid glands.

  PloS one 20100101

• Concomitant heterochromatinisation and down-regulation of gene expression unveils epigenetic silencing of RELB in an aggressive subset of chronic lymphocytic leukemia in males.

  BMC medical genomics 20100101

• Titrimetric immunohistochemical evaluation of DNA hypomethylation in uterine tumours.

  Journal of clinical pathology 20091101

• Frequent long-range epigenetic silencing of protocadherin gene clusters on chromosome 5q31 in Wilms' tumor.

  PLoS genetics 20091101

• Development of a novel output value for quantitative assessment in methylated DNA immunoprecipitation-CpG island microarray analysis.

  DNA research : an international journal for rapid publication of reports on genes and genomes 20091001

• Accurate measurement of DNA methylation that is traceable to the international system of units.

  Analytical chemistry 20090901

• A novel method to assess the full genome methylation profile using monoclonal antibody combined with the high throughput based microarray approach.

  Epigenetics 20090816

• DNA methyltransferase-mediated transcriptional silencing in malignant glioma: a combined whole-genome microarray and promoter array analysis.

  Oncogene 20090723

• Specific loss of histone H3 lysine 9 trimethylation and HP1gamma/cohesin binding at D4Z4 repeats is associated with facioscapulohumeral dystrophy (FSHD).

  PLoS genetics 20090701

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

  The Plant journal : for cell and molecular biology 20090201

• Methylated DNA immunoprecipitation (MeDIP).

  Methods in molecular biology (Clifton, N.J.) 20090101

• Remodeling of the chromatin structure of the facioscapulohumeral muscular dystrophy (FSHD) locus and upregulation of FSHD-related gene 1 (FRG1) expression during human myogenic differentiation.

  BMC biology 20090101

• Epigenetic differences in cortical neurons from a pair of monozygotic twins discordant for Alzheimer's disease.

  PloS one 20090101

• Effect of IVF and laser zona dissection on DNA methylation pattern of mouse zygotes.

  Mammalian genome : official journal of the International Mammalian Genome Society 20090101

• Global mapping of DNA methylation in mouse promoters reveals epigenetic reprogramming of pluripotency genes.

  PLoS genetics 20080601

• Degradation of several hypomodified mature tRNA species in Saccharomyces cerevisiae is mediated by Met22 and the 5'-3' exonucleases Rat1 and Xrn1.

  Genes & development 20080515

• Modifications in small interfering RNA that separate immunostimulation from RNA interference.

  Journal of immunology (Baltimore, Md. : 1950) 20080301

• Functional group and substructure searching as a tool in metabolomics.

  PloS one 20080101

• DNA methylation and histone acetylation patterns in cultured bovine fibroblasts for nuclear transfer.

  Molecular reproduction and development 20071201

• Increased urinary level of oxidized nucleosides in patients with mild-to-moderate Alzheimer's disease.

  Clinical biochemistry 20070901

• Incorporation of two modified nucleosides allows selective platination of an oligonucleotide making it suitable for duplex cross-linking.

  Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20070801

• Collision-induced dissociation of cytidine and its derivatives.

  Journal of mass spectrometry : JMS 20070101

• Modulation by decitabine of gene expression and growth of osteosarcoma U2OS cells in vitro and in xenografts: identification of apoptotic genes as targets for demethylation.

  Cancer cell international 20070101

• Postembryonic establishment of megabase-scale gene silencing in nucleolar dominance.

  PloS one 20070101

• Metabolic signature of breast cancer cell line MCF-7: profiling of modified nucleosides via LC-IT MS coupling.

  BMC biochemistry 20070101

• The structure of the RNA m5C methyltransferase YebU from Escherichia coli reveals a C-terminal RNA-recruiting PUA domain.

  Journal of molecular biology 20060721

• Modified nucleosides: an accurate tumour marker for clinical diagnosis of cancer, early detection and therapy control.

  British journal of cancer 20060605

• Epigenetic regulation: DNA confers identity but is not enough to maintain it.

  Genome biology 20060101

• Global DNA methylation evaluation: potential complementary marker in differential diagnosis of thyroid neoplasia.

  Virchows Archiv : an international journal of pathology 20050701

• Kilo-scale synthesis process for 2'-O-(2-methoxyethyl)-pyrimidine derivatives.

  Nucleosides, nucleotides & nucleic acids 20050101

• Activation-induced cytidine deaminase deaminates 5-methylcytosine in DNA and is expressed in pluripotent tissues: implications for epigenetic reprogramming.

  The Journal of biological chemistry 20041210

• The binding sites for the chromatin insulator protein CTCF map to DNA methylation-free domains genome-wide.

  Genome research 20040801

• Sequence- and base-specific delivery of nitric oxide to cytidine and 5-methylcytidine leading to efficient deamination.

  Journal of the American Chemical Society 20040728

• Determination of ribavirin in human serum and plasma by capillary electrophoresis.

  Electrophoresis 20040601

• DNA hypomethylation and imbalanced expression of DNA methyltransferases (DNMT1, 3A, and 3B) in human uterine leiomyoma.

  Gynecologic oncology 20030701

• Photophysical properties of 5-methylcytidine.

  Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20030401

• Singlet excited-state lifetimes of cytosine derivatives measured by femtosecond transient absorption.

  Photochemistry and photobiology 20030201

• Measurement of genome wide DNA methylation by reversed-phase high-performance liquid chromatography.

  Methods (San Diego, Calif.) 20020601

• 5-Methyldeoxycytidine monophosphate deaminase and 5-methylcytidyl-DNA deaminase activities are present in human mature sperm cells.

  FEBS letters 20020522

• Distinct nuclear organization, DNA methylation pattern and cytokinin distribution mark juvenile, juvenile-like and adult vegetative apical meristems in peach (Prunus persica (L.) Batsch).

  Journal of experimental botany 20020501

• Interaction of RNA with phage display selected peptides analyzed by capillary electrophoresis mobility shift assay.

  RNA (New York, N.Y.) 20020501

• Quantitative assessment of the use of modified nucleoside triphosphates in expression profiling: differential effects on signal intensities and impacts on expression ratios.

  BMC biotechnology 20020101

• Anticodon domain methylated nucleosides of yeast tRNA(Phe) are significant recognition determinants in the binding of a phage display selected peptide.

  Biochemistry 20011127

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

  Molecular pharmacology 20010501

• Synthesis of novel 3'-C-methylene thymidine and 5-methyluridine/cytidine H-phosphonates and phosphonamidites for new backbone modification of oligonucleotides.

  The Journal of organic chemistry 20010420

• Virtual combinatorial syntheses and computational screening of new potential anti-herpes compounds.

  Journal of medicinal chemistry 19990826

• Antisense oligonucleotide inhibition of hepatitis C virus (HCV) gene expression in livers of mice infected with an HCV-vaccinia virus recombinant.

  Antimicrobial agents and chemotherapy 19990201

• Synthesis and cytostatic and antiviral activities of 1-beta-D-ribofuranosyl-5-alkylcytosine (5-alkylcytidine) cyclic 3',5'-monophosphates.

  Journal of medicinal chemistry 19890101

• Inhibition of urethan induced lung tumour growth in strain A mice by 5-methyl cytidine.

  Cytobios 19800101