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A3656

5-Aza-2′-deoxycytidine

Name: 5-Aza-2&#8242;-deoxycytidine
Brand: SIGMA

≥97% (HPLC), powder, DNA methyltransferase inhibitor

Synonym(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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About This Item

Empirical Formula (Hill Notation):

C₈H₁₂N₄O₄

CAS Number:

2353-33-5

Molecular Weight:

228.21

NACRES:

NA.77

PubChem Substance ID:

24890797

UNSPSC Code:

12352200

EC Number:

219-089-4

MDL number:

MFCD00043011

Beilstein/REAXYS Number:

617982

Assay:

≥97%

Form:

powder

Quality level:

200

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Properties

Product Name

5-Aza-2′-deoxycytidine, ≥97%

Quality Level

200

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)

Description

General description

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.

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.

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 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.

This compound was developed by Eisai. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

When prepared properly, there may be a small amount of undissolved substance.

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pictograms

GHS08,GHS07

signalword

Danger

hcodes

H302,H315,H319,H335,H341,H360

pcodes

P202 - P261 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

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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