5-Aza-2prime-Deoxycytidine A Dnmt inhibitor shown to alter gene expression

5-Aza-2′-Deoxycytidine (CAS 2353-33-5)

5-Aza-2′-Deoxycytidine | CAS 2353-33-5 is rated 5.0 out of 5 by 1.
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Synonym: 5-Aza-CdR; 5-Aza-dC; Decitabine, 2'-Deoxy-5-azacytidine
Application: A Dnmt inhibitor shown to alter gene expression
CAS Number: 2353-33-5
Purity: ≥99%
Molecular Weight: 228.21
Molecular Formula: C8H12N4O4
* Refer to Certificate of Analysis for lot specific data (including water content).
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5-Aza-2′-Deoxycytidine, has been reported to cause phosphorylation inhibition of 2′-deoxycytidine in certain cells and the incorporation of 2′-deoxycytidine into DNA. Experiments have shown that this compound induces changes in the differentiated state of cultured mouse embryo cells and additionally inhibits Dnmt (DNA methyltransferase). DNA methylation has been noted to be important in determining apoptotic susceptibility to histone deacetylase inhibitors, and its prevention can cause gene silencing and transcriptional repression. Other studies suggest that cell exposure to 5-Aza-2′-Deoxycytidine causes a change in replication timing, reactivation of repressed genes, and decondensation of heterochromatin. Furthermore, this agent demonstrates the ability to induce histone hyperacetylation in murine centromeric heterochromatin and also affect intranuclear distribution of histone deacetylase 2.


References

1. Veselý, J., et al., 1977. Incorporation of a potent antileukemic agent, 5-aza-2'-deoxycytidine, into DNA of cells from leukemic mice. Cancer research. 37(10): 3684-9. PMID: 71199
2. Jones, P A., et al., 1980. Cellular differentiation, cytidine analogs and DNA methylation. Cell. 20(1): 85-93. PMID: 6156004
3. Zhu, W G., et al., 2001. DNA methyltransferase inhibition enhances apoptosis induced by histone deacetylase inhibitors. Cancer research. 61(4): 1327-33. PMID: 11245429
4. Takebayashi, S., et al., 2001. 5-Aza-2'-deoxycytidine induces histone hyperacetylation of mouse centromeric heterochromatin by a mechanism independent of DNA demethylation. Biochemical and biophysical research communications. 288(4): 921-6. PMID: 11688997

Usage :
Long term storage: 2 years at -20°C (Powder); 6 monthsat -80°C (in DMSO).
Physical State :
Solid
Solubility :
Soluble in water (50 mM), methanol (1 mg/ml), DMSO (50 mg/ml), DMF (~20 mg/ml), and ethanol (5 mM).
Storage :
Store at 4° C
Melting Point :
~200° C (dec.)
Boiling Point :
485.80° C at 760 mmHg (Predicted)
Density :
1.91 g/cm3 (Predicted)
Refractive Index :
n20D 1.78 (Predicted)
Optical Activity :
α20/D +72°, c = 0.5 in water
IC50 :
Dnmt: IC50 = 4.38 nM (KG1a cells); Dnmt: IC50 = 438 nM (HL-60 cells)
pK Values :
pKb: 3.49 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
XZ3012000
PubChem CID :
451668
Merck Index :
14: 2853
MDL Number :
MFCD00043011
EC Number :
219-089-4
Beilstein Registry :
617982
SMILES :
NC1=NC(=O)N(C=N1)[C@H]1C[C@@H](O)[C@@H](CO)O1

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Certificate of Analysis

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5-Aza-2prime-Deoxycytidine  Product Citations

See how others have used 5-Aza-2prime-Deoxycytidine. Click on the entry to view the PubMed entry .

Citations 1 to 1 of 1 total

PMID: # 12591989  Sato, N. et al. 2003. J. Natl. Cancer Inst. 95: 327-330.

Citations 1 to 1 of 1 total

Dear sir, this is vertica, senior research fellow, working at biophysics dept, AIIMS. I'm a happy customer of Santa cruz Biotech.I would like to place a request here that can you provide me a sample of this compound so that i could place an order further.

Asked by: Vertica Agnihotri
Thank you for your question. We are so glad to hear that you are a happy customer of Santa Cruz Biotechnology! We do not typically provide sample sizes of our chemical products. If you plan to place a bulk order of this compound, and would first like to test a smaller size, please contact our Special Orders Coordinator. Please e-mail <specialorders@scbt.com>.
Answered by: Technical Support
Date published: 2017-05-31

What is the storage of the compound after being dissolved in water?

Asked by: two2igm05
Thank you for your question. 5-Aza-2′-Deoxycytidine, sc-202424, can be stored for 3 years at -20℃ as a powder or for 6 months at -80℃ in solvent.
Answered by: TechService7
Date published: 2017-01-16

What is the solubility of this chemical?

Asked by: two2igm05
Thank you for your question. This chemical, 5-Aza-2′-Deoxycytidine (CAS 2353-33-5), is soluble in DMSO (45 mg/ml), water (10 mg/ml) and ethanol (<1 mg/ml).
Answered by: Technical Support
Date published: 2016-12-14
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Rated 5 out of 5 by from Sato Sato, N. et al. (PubMed 12591989) studied the effects of 5-Aza-2 -Deoxycytidine, a Dnmt inhibitor shown to alter gene expression, on matrix metalloproteinase (MMP) expression and pancreatic cancer cell invasiveness. They found a significant increase in invasive potential in 4/5 pancreatic cell lines after treatment with 5-Aza-2 -Deoxycytidine. This enhanced invasiveness was associated with the induction on mRNAs for one or more MMPs critical for tumor invasion. -SCBT Publication Review
Date published: 2015-05-08
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