A3656
5-Aza-2′-deoxycytidine
≥97% (HPLC), powder, DNA methyltransferase inhibitor
Synonyme(s) :
2′-Deoxy-5-azacytidine, 4-Amino-1-(2-deoxy-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Decitabine
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A propos de cet article
Formule empirique (notation de Hill) :
C8H12N4O4
Numéro CAS:
Poids moléculaire :
228.21
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
219-089-4
MDL number:
Beilstein/REAXYS Number:
617982
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Laissez-nous vous aiderNom du produit
5-Aza-2′-deoxycytidine, ≥97%
Quality Level
assay
≥97%
form
powder
solubility
acetic acid: water (1:1): 50 mg/mL
originator
Eisai
SMILES string
NC1=NC(=O)N(C=N1)[C@H]2C[C@H](O)[C@@H](CO)O2
InChI
1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5+,6+/m0/s1
InChI key
XAUDJQYHKZQPEU-KVQBGUIXSA-N
Gene Information
human ... DNMT1(1786), DNMT3A(1788)
General description
5-Aza-2′-deoxycytidine, also known as Decitabine, is a DNA-hypomethylating agent that promotes differentiation and apoptosis in leukemic cells. It is a 2′-deoxycytidine analog that causes DNA demethylation or hemi-demethylation, which can regulate gene expression by "opening" the chromatin structure, making it more sensitive to nucleases. This chromatin remodeling allows transcription factors to bind to promoter regions, facilitating the assembly of the transcription complex and subsequent gene expression. As an epigenetic modifier, Decitabine inhibits DNA methyltransferase activity, leading to DNA hypomethylation and gene activation. The reactivation of genes is further enhanced when demethylation is combined with histone hyperacetylation. Decitabine is used to treat chronic myelomonocytic leukemia, refractory anemia, myelodysplastic syndrome, and acute myeloid leukemia.
5-Aza-2′-deoxycytidine is a DNA-hypomethylating agent, which stimulates differentiation and apoptosis of leukemic cells. It is a 2′-deoxycytidine analogue. 5-Aza-2′-deoxycytidine is used to treat chronic myelomonocytic leukemia, refractory anemia, myelodysplastic syndrome and acute myeloid leukemia.
Application
5-Aza-2′-deoxycytidine has been used as a demethylating agent in breast cancer cell line, chromatin, DNA and promoter region of p16 gene.
Biochem/physiol Actions
5′-Azadeoxycytidine causes DNA demethylation or hemi-demethylation. DNA demethylation can regulate gene expression by "opening" the chromatin structure detectable as increased nuclease sensitivity. This remodeling of chromatin structure allows transcription factors to bind to the promoter regions, assembly of the transcription complex, and gene expression. Decitabine is an epigenetic modifier that inhibits DNA methyltransferase activity which results in DNA demethylation (hypomethylation) and gene activation by remodeling "opening" chromatin. Genes are synergistically reactivated when demethylation is combined with histone hyperacetylation.
Features and Benefits
This compound was developed by Eisai. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
Preparation Note
When prepared properly, there may be a small amount of undissolved substance.
signalword
Danger
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Classe de stockage
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Contenu apparenté
Zhen Liang et al.
Molecular cancer, 16(1), 96-96 (2017-05-28)
Current evidence indicates that miR-608 is widely down-regulated in various malignant tumors including liver cancer, colon cancer, lung cancer and glioma, and acts as a tumor suppressor by inhibiting cell proliferation, invasion and migration or by promoting apoptosis. The specific
Enhancement of chemotherapeutic efficacy in hypermethylator breast cancer cells through targeted and pharmacologic inhibition of DNMT3b
Sandhu R, et al.
Breast Cancer Research and Treatment, 131(2), 385-399 (2012)
Hypermethylation in the p16 promoter region in the carcinogenesis of endometrial cancer in Japanese patients
Yanokura M, et al.
Anticancer Research, 26(2A), 851-856 (2006)