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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

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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

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

wgk_germany

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’.

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