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Merck

189825

5-Aza-2′-Deoxycytidine

A cytosine analog that acts as a DNA methyltransferase inhibitor.

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C8H12N4O4
Numéro CAS:
Poids moléculaire :
228.21
UNSPSC Code:
12352208
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
Form:
lyophilized
Quality level:
Storage condition:
OK to freeze
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Quality Level

description

RTECS - XZ3012000

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

SMILES string

N2(C=NC(=N)NC2=O)C1OC(C(C1)O)CO

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).

Biochem/physiol Actions

Primary Target
DNA methyltransferase inhibitor

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
warming is required to achieve complete solubilization

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

Disclaimer

Toxicity: Harmful & Carcinogenic / Teratogenic (E)


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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

Classe de stockage

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

wgk

WGK 3



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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
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