5-Methyl-2'-deoxycytidine
- CAS NO.:838-07-3
- Empirical Formula: C10H15N3O4
- Molecular Weight: 241.24
- MDL number: MFCD00006549
- EINECS: 212-655-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-06-08 09:02:17
What is 5-Methyl-2'-deoxycytidine?
Description
5-Methyl-2'-deoxycytidine is a nucleoside analogue that inhibits the synthesis of DNA. 5-Methyl-2'-deoxycytidine prevents methylation of guanine, which disrupts the binding of guanine nucleotide-binding proteins to the dna template and prevents polymerase chain reactions. 2'-Deoxy-5-methylcytidine is also a methyltransferase inhibitor, which means it blocks the enzyme responsible for adding methyl groups to cytosine molecules.
Chemical properties
White Solid
The Uses of 5-Methyl-2'-deoxycytidine
5-Methyl-2'-deoxycytidine is a pyrimidine nucleoside that when incorporated into single-stranded DNA can act in cis to signal de novo DNA methylation. It has been used in epigenetics research to investigate the dynamics of DNA methylation pattern in the control of gene expression.
The Uses of 5-Methyl-2'-deoxycytidine
A Cytidine (C998300) analog and also an isostere of Thymidine (T412000).
The Uses of 5-Methyl-2'-deoxycytidine
5-Methyl-2'-deoxycytidine in single-stranded DNA can act in cis to signal de novo DNA methylation.
What are the applications of Application
5-Methyl-2′-deoxycytidine is a pyrimidine nucleoside isostere of thymidine, and analog of cytidine.
Definition
ChEBI: 5-methyl-2'-deoxycytidine is a 2'-deoxycytidine.
General Description
Giel-Pietraszuk et al. developed a new method for quantification of 5-methyl-2'-deoxycytidine (m5C) in the DNA. The technique is based on the conversion of m5C into fluorescent 3, N4-etheno-5-methyl-2'-deoxycytidine (εm5C) and its identification by reversed-phase high-performance liquid chromatography (RP-HPLC)[1].The measurement of 5-meC and 5-medC in urine may help assess changes in DNA methylation status in the whole body and investigate the DNA demethylation mechanism in vivo. 5-MedC was first detected in urine using an inhibition ELISA method;12 however, because ELISA may suffer from poor selectivity and sensitivity, later urinary measurements of 5-medC were developed mainly based on the chromatographic techniques[2].
References
[1] Ma?gorzata Giel-Pietraszuk. “Quantification of 5-methyl-2’-deoxycytidine in the DNA.” Acta biochimica Polonica 62 2 (2015): 281–6.
[2] Chiung-Wen Hu. “Direct Analysis of 5-Methylcytosine and 5-Methyl-2′-deoxycytidine in Human Urine by Isotope Dilution LC-MS/MS: Correlations with N-Methylated Purines and Oxidized DNA Lesions.” Chemical Research in Toxicology 25 2 (2012): 462–470.
Properties of 5-Methyl-2'-deoxycytidine
Melting point: | 217-219 °C(lit.) |
Boiling point: | 492.8±55.0 °C(Predicted) |
Density | 1?+-.0.1 g/cm3(Predicted) |
refractive index | 44 ° (C=1.4, H2O) |
storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
solubility | DMSO (Slightly, Heated), Methanol (Slightly, Heated), Water (Slightly) |
pka | pK1:4.33 (25°C) |
form | Powder |
color | White to Off-white |
Water Solubility | Soluble in water. |
Stability: | Hygroscopic |
CAS DataBase Reference | 838-07-3(CAS DataBase Reference) |
Safety information for 5-Methyl-2'-deoxycytidine
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 5-Methyl-2'-deoxycytidine
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