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A3656

Sigma-Aldrich

5-Aza-2′-deoxycytidine

≥97%

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Synonym(s):
2′-Deoxy-5-azacytidine, 4-Amino-1-(2-deoxy-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Decitabine
Empirical Formula (Hill Notation):
C8H12N4O4
CAS Number:
2353-33-5
Molecular Weight:
228.21
Beilstein:
617982
EC Number:
219-089-4
MDL number:
MFCD00043011
UNSPSC Code:
12352200
PubChem Substance ID:
24890797
NACRES:
NA.77

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)

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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

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How should Product A3656, 5-Aza-2´-deoxycytidine, be dissolved?

    This product is typically dissolved at 50 mg/ml in 50% acetic acid to yield a clear colorless solution. This product is also soluble at 50 mg/ml in DMSO or 0.25 mg/ml in water.

  4. What is the solution stability of Product A3656, 5-Aza-2´-deoxycytidine? 

    Aqueous solutions of this product appear to be very unstable, probably by analogy to A2385, aza-cytidine. We suggest preparing solution fresh for each use and storing solutions on ice until use within a few hours.  

  5. What is the difference between 5-Aza-2´-deoxycytidine Products A3656 and A1287?

    Both of these products inhibit DNA methyltransferase.  However, they are different chemicals.  Product No. A3656 is 5-Aza-2´-deoxycytidine and A1287 is 5-Azacytidine. Product No. A1287 is γ-irradiated, hybridoma- and endotoxin-tested, and Product No. A3656 is not.

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Molecular, cellular and animal pharmacology of 5-aza-2'-deoxycytidine.
R L Momparler
Pharmacology & therapeutics, 30(3), 287-299 (1985-01-01)
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
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)
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
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)
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