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189825

Sigma-Aldrich

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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About This Item

Formule empirique (notation de Hill):
C8H12N4O4
Numéro CAS:
2353-33-5
Poids moléculaire :
228.21
Numéro MDL:
MFCD00043011
Code UNSPSC :
12352208
Nomenclature NACRES :
NA.77

Niveau de qualité

200

Pureté

≥98% (HPLC)

Forme

lyophilized

Fabricant/nom de marque

Calbiochem®

Conditions de stockage

OK to freeze

Solubilité

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

Conditions d'expédition

ambient

Température de stockage

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)

Clé InChI

XAUDJQYHKZQPEU-UHFFFAOYSA-N

Description générale

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.

Actions biochimiques/physiologiques

Primary Target
DNA methyltransferase inhibitor

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Notes préparatoires

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.

Autres remarques

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.

Informations légales

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

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

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

Classe de danger pour l'eau (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
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
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
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
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
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