Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H15N3O5 |
| Molecular Weight | 257.2432 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N=C1N
InChI
InChIKey=ZAYHVCMSTBRABG-JXOAFFINSA-N
InChI=1S/C10H15N3O5/c1-4-2-13(10(17)12-8(4)11)9-7(16)6(15)5(3-14)18-9/h2,5-7,9,14-16H,3H2,1H3,(H2,11,12,17)/t5-,6-,7-,9-/m1/s1
| Molecular Formula | C10H15N3O5 |
| Molecular Weight | 257.2432 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
5-methyl cytidine has been indicated in the controlling mechanism for the genetic change, which leads to cancer. Human APOBEC3A (A3A), a polynucleotide cytidine deaminase (PCD) with specificity for single stranded DNA, can extensively deaminate human nuclear DNA. It was discovered that A3A among all human PCDs can deaminate 5-methylcytidine in a variety of single stranded DNA substrates both in vitro and in transfected cells almost as efficiently as cytidine itself. As 5MeCpG deamination hotspots characterize many genes associated with cancer it was made suggestion that A3A is a major player in the onset of cancer.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inhibition of urethan induced lung tumour growth in strain A mice by 5-methyl cytidine. | 1980 |
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| The nature of cancer and the mechanisms of its control: a review. | 1980 |
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| Monitoring of urinary excretion of modified nucleosides in cancer patients using a set of six monoclonal antibodies. | 1992 Jan 31 |
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| Immunochemical detection of urinary 5-methyl-2'-deoxycytidine as a potential biologic marker for leukemia. | 1995 Jan 31 |
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| Anticodon domain methylated nucleosides of yeast tRNA(Phe) are significant recognition determinants in the binding of a phage display selected peptide. | 2001 Nov 27 |
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| Quantitative assessment of the use of modified nucleoside triphosphates in expression profiling: differential effects on signal intensities and impacts on expression ratios. | 2002 Jul 31 |
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| Measurement of genome wide DNA methylation by reversed-phase high-performance liquid chromatography. | 2002 Jun |
|
| Interaction of RNA with phage display selected peptides analyzed by capillary electrophoresis mobility shift assay. | 2002 May |
|
| Distinct nuclear organization, DNA methylation pattern and cytokinin distribution mark juvenile, juvenile-like and adult vegetative apical meristems in peach (Prunus persica (L.) Batsch). | 2002 May |
|
| 5-Methyldeoxycytidine monophosphate deaminase and 5-methylcytidyl-DNA deaminase activities are present in human mature sperm cells. | 2002 May 22 |
|
| Photophysical properties of 5-methylcytidine. | 2003 Apr |
|
| Singlet excited-state lifetimes of cytosine derivatives measured by femtosecond transient absorption. | 2003 Feb |
|
| DNA hypomethylation and imbalanced expression of DNA methyltransferases (DNMT1, 3A, and 3B) in human uterine leiomyoma. | 2003 Jul |
|
| A rapid and sensitive method for quantitation of nucleosides in human urine using liquid chromatography/mass spectrometry with direct urine injection. | 2004 |
|
| The binding sites for the chromatin insulator protein CTCF map to DNA methylation-free domains genome-wide. | 2004 Aug |
|
| Activation-induced cytidine deaminase deaminates 5-methylcytosine in DNA and is expressed in pluripotent tissues: implications for epigenetic reprogramming. | 2004 Dec 10 |
|
| Sequence- and base-specific delivery of nitric oxide to cytidine and 5-methylcytidine leading to efficient deamination. | 2004 Jul 28 |
|
| Determination of ribavirin in human serum and plasma by capillary electrophoresis. | 2004 Jun |
|
| Kilo-scale synthesis process for 2'-O-(2-methoxyethyl)-pyrimidine derivatives. | 2005 |
|
| Global DNA methylation evaluation: potential complementary marker in differential diagnosis of thyroid neoplasia. | 2005 Jul |
|
| Epigenetic regulation: DNA confers identity but is not enough to maintain it. | 2006 |
|
| The structure of the RNA m5C methyltransferase YebU from Escherichia coli reveals a C-terminal RNA-recruiting PUA domain. | 2006 Jul 21 |
|
| Modified nucleosides: an accurate tumour marker for clinical diagnosis of cancer, early detection and therapy control. | 2006 Jun 5 |
|
| Incorporation of two modified nucleosides allows selective platination of an oligonucleotide making it suitable for duplex cross-linking. | 2007 Aug |
|
| DNA methylation and histone acetylation patterns in cultured bovine fibroblasts for nuclear transfer. | 2007 Dec |
|
| Collision-induced dissociation of cytidine and its derivatives. | 2007 Jan |
|
| Postembryonic establishment of megabase-scale gene silencing in nucleolar dominance. | 2007 Nov 7 |
|
| Increased urinary level of oxidized nucleosides in patients with mild-to-moderate Alzheimer's disease. | 2007 Sep |
|
| 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. | 2007 Sep 10 |
|
| Methylated DNA immunoprecipitation (MeDIP). | 2009 |
|
| A novel method to assess the full genome methylation profile using monoclonal antibody combined with the high throughput based microarray approach. | 2009 Aug 16 |
|
| Specific loss of histone H3 lysine 9 trimethylation and HP1gamma/cohesin binding at D4Z4 repeats is associated with facioscapulohumeral dystrophy (FSHD). | 2009 Jul |
|
| Frequent long-range epigenetic silencing of protocadherin gene clusters on chromosome 5q31 in Wilms' tumor. | 2009 Nov |
|
| Titrimetric immunohistochemical evaluation of DNA hypomethylation in uterine tumours. | 2009 Nov |
|
| Development of a novel output value for quantitative assessment in methylated DNA immunoprecipitation-CpG island microarray analysis. | 2009 Oct |
|
| Accurate measurement of DNA methylation that is traceable to the international system of units. | 2009 Sep 1 |
|
| Effect of IVF and laser zona dissection on DNA methylation pattern of mouse zygotes. | 2009 Sep-Oct |
|
| Multi-site-specific 16S rRNA methyltransferase RsmF from Thermus thermophilus. | 2010 Aug |
|
| 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. | 2010 Aug 18 |
|
| Crystal structure of Methanocaldococcus jannaschii Trm4 complexed with sinefungin. | 2010 Aug 20 |
|
| Structure of an archaeal homologue of the bacterial Fmu/RsmB/RrmB rRNA cytosine 5-methyltransferase. | 2010 Dec |
|
| A quantitative systems approach reveals dynamic control of tRNA modifications during cellular stress. | 2010 Dec 16 |
|
| Ribonucleoside labeling with Os(VI): a methodological approach to evaluation of RNA methylation by HPLC-ICP-MS. | 2010 Feb |
|
| Generation of a recombinant single-chain variable fragment (scFv) targeting 5-methyl-2'-deoxycytidine. | 2010 Jan |
|
| Genome-wide DNA methylation profiling reveals novel epigenetically regulated genes and non-coding RNAs in human testicular cancer. | 2010 Jan 19 |
|
| Altered intra-nuclear organisation of heterochromatin and genes in ICF syndrome. | 2010 Jun 29 |
|
| Nanomechanical recognition measurements of individual DNA molecules reveal epigenetic methylation patterns. | 2010 Nov |
|
| AutoMeDIP-seq: a high-throughput, whole genome, DNA methylation assay. | 2010 Nov |
|
| Concomitant heterochromatinisation and down-regulation of gene expression unveils epigenetic silencing of RELB in an aggressive subset of chronic lymphocytic leukemia in males. | 2010 Nov 10 |
|
| Transcriptome, methylome and genomic variations analysis of ectopic thyroid glands. | 2010 Oct 15 |
Patents
Sample Use Guides
In Vitro Use Guide
Curator's Comment: As several TP53 CpG methylation sites are mutational hotspots in cancer, an oligodeoxynucleotide corresponding to part of exon 8 was synthesized with 5-methylcytidine (5MeC) incorporated at two known sites of methylation in codons 273 and 282. Following incubation with purified myc-His6-tagged A3A (human APOBEC3A (A3A), a polynucleotide cytidine deaminase (PCD)) and recovery of products by standard PCR, both 5MeC and C were readily deaminated in a comparable manner. Given that 5MeC is deaminated by A3A the singularity of 5MeCpG mutation hotspots in cancer probably has more to do with the relative efficiency of T:G mismatch repair compared to highly efficient U:G repair initiated by UNG.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 15:16:09 UTC 2023
by
admin
on
Thu Jul 06 15:16:09 UTC 2023
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| Record UNII |
TL9PB228DC
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| Record Status |
Validated (UNII)
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| Record Version |
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363933
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92918
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2140-61-6
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DTXSID401016977
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5-Methylcytidine
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TL9PB228DC
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218-390-8
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