189825

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

Properties

• 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

Description

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

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H302,H315,H319,H335,H341,H360
• Precautionary Statements: P201 - P202 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• 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