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Submit Review5-Azacytidine
Description: DNA methyltransferase inhibitor
Chemical Name: 4-Amino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one
Purity: ≥98% (HPLC)
Biological Activity for 5-Azacytidine
5-Azacytidine is a DNA methyltransferase inhibitor. Incorporates into DNA forming covalent adducts with cellular DNMT1, depleting enzyme activity. Induces demethylation and reactivation of silenced genes. Improves the efficiency of reprogramming of stem cells; induces differentiation of mesenchymal stem cells into cardiomyocytes.
Compound Libraries for 5-Azacytidine
5-Azacytidine is also offered as part of the Tocriscreen 2.0 Max and Tocriscreen Stem Cell Library. Find out more about compound libraries available from Tocris.
Technical Data for 5-Azacytidine
| M. Wt | 244.2 |
| Formula | C8H12N4O5 |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 320-67-2 |
| PubChem ID | 9444 |
| InChI Key | NMUSYJAQQFHJEW-KVTDHHQDSA-N |
| Smiles | O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N2C(N=C(N)N=C2)=O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for 5-Azacytidine
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 12.21 | 50 | |
| DMSO | 24.42 | 100 |
Preparing Stock Solutions for 5-Azacytidine
The following data is based on the product molecular weight 244.2. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 4.1 mL | 20.48 mL | 40.95 mL |
| 5 mM | 0.82 mL | 4.1 mL | 8.19 mL |
| 10 mM | 0.41 mL | 2.05 mL | 4.1 mL |
| 50 mM | 0.08 mL | 0.41 mL | 0.82 mL |
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Product Datasheets for 5-Azacytidine
References for 5-Azacytidine
References are publications that support the biological activity of the product.
Schneider-Stock et al (2005) 5-aza-Cytidine is a potent inhibitor of DNA methyltransferase 3a and induces apoptosis in HCT-116 colon cancer cells via Gadd45- and p53-dependent mechanisms. J.Pharmacol.Exp.Ther. 312 525 PMID: 15547111
Mikkelsen et al (2008) Dissecting direct reprogramming through integrative genomic analysis. Nature 454 49 PMID: 18509334
Qian et al (2012) 5-Azacytidine induces cardiac differentiation of human umbilical cord-derived mesenchymal stem cells by activating extracellular regulated kinase. Stem Cells Dev. 21 67 PMID: 21476855
If you know of a relevant reference for 5-Azacytidine, please let us know.
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Keywords: 5-Azacytidine, 5-Azacytidine supplier, DNA, methyltransferases, methylation, inhibits, inhibitors, DNMT, mesenchymal, stem, cells, reprogramming, differentiation, differentiating, cardiomyocytes, epigenetics, Methyltransferases, Stem, Cell, Reprogramming, Mesenchymal, Cells, Cardiomyocyte, 3842, Tocris Bioscience
⚠ WARNING: This product can expose you to chemicals including Azacitidine, which is known to the State of California to cause cancer. For more information, go to www.P65Warnings.ca.gov
6 Citations for 5-Azacytidine
Citations are publications that use Tocris products. Selected citations for 5-Azacytidine include:
Chong et al (2013) Progenitor cells identified by PDGFR-α expression in the developing and diseased human heart. Cell Res 22 1932 PMID: 23391309
Perera et al (2009) Relation of DNA methylation of 5'-CpG island of ACSL3 to transplacental exposure to airborne polycyclic aromatic hydrocarbons and childhood asthma. PLoS One 4 e4488 PMID: 19221603
Linscott and Chung (2019) TET1 regulates fibroblast growth factor 8 transcription in Gn releasing hormone neurons. PLoS One 14 e0220530 PMID: 31361780
Bhuvanagiri et al (2014) 5-azacytidine inhibits nonsense-mediated decay in a MYC-dependent fashion. EMBO Mol Med 6 1593 PMID: 25319547
Donald J et al (2017) Epigenetic modifiers upregulate MHC II and impede ovarian cancer tumor growth. Oncotarget 8 44159-44170 PMID: 28498806
Chandrakanthan et al (2016) PDGF-AB and 5-Azacytidine induce conversion of somatic cells into tissue-regenerative multipotent stem cells Proc Natl Acad Sci U S A 113 E2306 PMID: 27044077
Do you know of a great paper that uses 5-Azacytidine from Tocris? Please let us know.
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Literature in this Area
Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!
*Please note that Tocris will only send literature to established scientific business / institute addresses.
Cell Cycle and DNA Damage Research Product Guide
This product guide provides a review of the cell cycle and DNA damage research area and lists over 150 products, including research tools for:
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Epigenetics in Cancer Research Product Guide
This product guide reviews some of the main areas in cancer epigenetics research and lists around 120 products that can be used for the main epigenetic targets including:
- Histone Methylation
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Epigenetics Scientific Review
Written by Susanne Müller-Knapp and Peter J. Brown, this review gives an overview of the development of chemical probes for epigenetic targets, as well as the impact of these tool compounds being made available to the scientific community. In addition, their biological effects are also discussed. Epigenetic compounds available from Tocris are listed.