Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

189825

Sigma-Aldrich

5-Aza-2′-Deoxycytidine

A cytosine analog that acts as a DNA methyltransferase inhibitor.

Synonym(s):

5-Aza-2′-Deoxycytidine, 5-Aza-CdR, 5-Aza-dC, 2′-Deoxy-5-azacytidine, Decitabine

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C8H12N4O4
CAS Number:
2353-33-5
Molecular Weight:
228.21
MDL number:
MFCD00043011
UNSPSC Code:
12352208
NACRES:
NA.77

Quality Level

200

Assay

≥98% (HPLC)

form

lyophilized

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

solubility

methanol: 1 mg/mL
50% acetic acid: 25 mg/mL
DMSO: 25 mg/mL

shipped in

ambient

storage temp.

2-8°C

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)

InChI key

XAUDJQYHKZQPEU-UHFFFAOYSA-N

General description

A cytosine analog that acts as a DNA methyltransferase inhibitor. Restores caspase-8 and caspase-10 mRNA and protein expression as well as TRAIL (Tumor necrosis factor-Related Apoptosis Inducing Ligand) sensitivity in TRAIL-resistant cell lines. Also enhances apoptosis induced by HDAC (Histone Deacetylase) inhibitors. Also available as a 100 mM solution in DMSO (Cat. No. 189826).
A cytosine analog that acts as a DNA methyltransferase inhibitor. Shown to restore mRNA and protein expression of caspase-8 and Tumor Necrosis Factor-Related Apoptosis Inducing Ligand (TRAIL) sensitivity of resistant cell lines. Also reported to enhance apoptosis induced by histone deacetylase (HDAC) inhibitors.

Biochem/physiol Actions

Primary Target
DNA methyltransferase inhibitor

Packaging

Packaged under inert gas

Warning

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Preparation Note

warming is required to achieve complete solubilization

Reconstitution

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Eggert, A., et al. 2001. Cancer Res.61, 1314.
Takebayashi, S., et al. 2001. Biochem. Biophys. Res. Commun.288, 921.
Zhu, W.G., et al. 2001. Cancer Res.61, 1327.
Hopkins-Donaldson, S., et al. 2000. Cancer Res.60, 4315.
Haaf, T. 1995. Pharmacol. Ther.65, 19.
Jones, P.A., and Taylor, S.M. 1980. Cell20, 85.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

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

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

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’.

Already Own This Product?

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

Visit the Document Library

Jia-Xue Sun et al.
Epigenetics, 19(1), 2337087-2337087 (2024-04-02)
Decidual macrophages are the second-largest immune cell group at the maternal-foetal interface. They participate in apoptotic cell removal, and protect the foetus from microorganisms or pathogens. Dysfunction of decidual macrophages gives rise to pregnancy complications such as preeclampsia and recurrent
Jingjing Du et al.
Gut microbes, 13(1), 1-19 (2021-02-09)
Betaine is a natural compound present in commonly consumed foods and may have a potential role in the regulation of glucose and lipids metabolism. However, the underlying molecular mechanism of its action remains largely unknown. Here, we show that supplementation
Bin Xie et al.
Cell biology international, 46(11), 1900-1914 (2022-08-23)
Ras-association domain family 1A (RASSF1A) is one of the most methylated genes in lung cancer (LC). We investigate whether the high DNA methylation level of RASSF1A can relieve the resistance of RASSF1A to LC by inhibiting RASSF1A's transcription factor binding
Carl M Gay et al.
Cancer cell, 39(3), 346-360 (2021-01-23)
Despite molecular and clinical heterogeneity, small cell lung cancer (SCLC) is treated as a single entity with predictably poor results. Using tumor expression data and non-negative matrix factorization, we identify four SCLC subtypes defined largely by differential expression of transcription
Adam W Watson et al.
Cell reports, 35(13), 109293-109293 (2021-07-01)
While the immediate and transitory response of breast cancer cells to pathological stiffness in their native microenvironment has been well explored, it remains unclear how stiffness-induced phenotypes are maintained over time after cancer cell dissemination in vivo. Here, we show that
View All Related Papers

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