Skip to Content
Merck

A3656

5-Aza-2′-deoxycytidine

≥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

Sign In to View Organizational & Contract Pricing.

Select a Size

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

5-Aza-2′-deoxycytidine, ≥97%

InChI key

XAUDJQYHKZQPEU-KVQBGUIXSA-N

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

SMILES string

NC1=NC(=O)N(C=N1)[C@H]2C[C@H](O)[C@@H](CO)O2

assay

≥97%

form

powder

solubility

acetic acid: water (1:1): 50 mg/mL

originator

Eisai

Quality Level

200

Gene Information

human ... DNMT1(1786), DNMT3A(1788)

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.

pictograms

Health hazardExclamation mark
GHS08,GHS07

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

A3656-VAR: + A3656-BULK: + A3656-50MG: + A3656-25MG: + A3656-10MG: + A3656-5MG:

jan

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCF7170
BCCD6249
SLCD8823
SLCD3551
WXBC9633V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Jia-Yu Zhong et al.
Aging, 11(14), 5232-5245 (2019-07-29)
Cortisol-producing adenoma (CPA) is the main cause of Adrenal Cushing syndrome. However, its molecular mechanism is not fully understood. Previous study revealed Synaptophysin (SYP) is ubiquitously expressed in adrenocortical tumors, but its function in CPA still need to be discovered.
Amanda Cabrera-Mulero et al.
Journal of clinical medicine, 8(7) (2019-07-20)
The relationship between body weight and different cancers is now well-recognized and among such cancers, colorectal cancer (CRC) is reported most frequently. Our group recently published findings, through an epigenome-wide association study, suggesting that body mass index (BMI) could act
Decitabine in the treatment of acute myeloid leukemia in elderly patients
Malik P and Cashen AF
Cancer Management and Research, 6, 53-53 (2014)
Vinay Koshy Varghese et al.
Life sciences, 232, 116668-116668 (2019-07-22)
Gene regulatory mechanisms determine the multistep carcinogenesis process. Two aspects of epigenetics are microRNA (miRNAs) and DNA methylation that regulate distinct biological mechanisms such as metastasis, apoptosis cell proliferation and induction of senescence. Although critical, the interplay between these two
Molecular, cellular and animal pharmacology of 5-aza-2'-deoxycytidine.
R L Momparler
Pharmacology & therapeutics, 30(3), 287-299 (1985-01-01)
View All Related Papers

Articles

Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.

Bis-Trisポリアクリルアミドゲル電気泳動技術

迅速かつ確実なゲルキャスティングとタンパク質分離のためにmPAGE® TurboMixテクノロジーを用いるBis-Tris SDS-PAGEゲルキャスティングキット。

Bis Tris Polyacrylamide Gel Electrophoresis Technology

Bis-Tris SDS-PAGE gel casting kits with mPAGE® TurboMix technology for rapid, reliable gel casting and protein separation.

See All

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service