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Submit Review3-Deazaneplanocin A hydrochloride
Description: EZH2 histone methyltransferase inhibitor
Alternative Names: DZNep,NSC 617989
Chemical Name: (1S,2R,5R)-5-(4-Amino-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)-3-cyclopentene-1,2-diol hydrochloride
Purity: ≥98% (HPLC)
Biological Activity for 3-Deazaneplanocin A hydrochloride
3-Deazaneplanocin A hydrochloride is a histone methyltransferase inhibitor; decreases global histone methylation. 3-Deazaneplanocin A hydrochloride inhibits EZH2 histone methyltransferase and s-adenosylhomocysteine (SAH) hydrolase activity. Blocks trimethylation of lysine 27 on histone H3 and lysine 20 on histone H4 in vitro. 3-Deazaneplanocin A hydrochloride induces apoptosis in multiple cancer cell lines and has no apoptotic effect on normal cells. Enhances Oct4 expression in chemically induced pluripotent stem cells (CiPSCs).
DZNep synthesized to Ancillary Material Grade also available.
For more information about how 3-Deazaneplanocin A hydrochloride may be used, see our protocol: Highly Efficient Generation of CiPSCs from MEFs
Technical Data for 3-Deazaneplanocin A hydrochloride
| M. Wt | 298.73 |
| Formula | C12H14N4O3.HCl |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 120964-45-6 |
| PubChem ID | 14563109 |
| InChI Key | UNSKMHKAFPRFTI-FDKLLANESA-N |
| Smiles | OCC([C@@H](O)[C@H]3O)=C[C@H]3N2C=NC1=C(N)N=CC=C12.Cl |
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 3-Deazaneplanocin A hydrochloride
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 2.99 | 10 |
Preparing Stock Solutions for 3-Deazaneplanocin A hydrochloride
The following data is based on the product molecular weight 298.73. 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 |
|---|---|---|---|
| 0.1 mM | 33.48 mL | 167.38 mL | 334.75 mL |
| 0.5 mM | 6.7 mL | 33.48 mL | 66.95 mL |
| 1 mM | 3.35 mL | 16.74 mL | 33.48 mL |
| 5 mM | 0.67 mL | 3.35 mL | 6.7 mL |
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Product Datasheets for 3-Deazaneplanocin A hydrochloride
References for 3-Deazaneplanocin A hydrochloride
References are publications that support the biological activity of the product.
Tan et al (2007) Pharmacologic disruption of Polycomb-repressive complex 2-mediated gene repression selectively induces apoptosis in cancer cells. Genes Dev. 21 1050 PMID: 17437993
Miranda et al (2009) DZNep is a global histone methylation inhibitor that reactivates developmental genes not silenced by DNA methylation. Mol.Cancer Ther. 8 1579 PMID: 19509260
Tseng et al (1989) Synthesis of 3-deazaneplanocin A, a powerful inhibitor of S-adenosylhomocysteine hydrolase with potent and selective in vitro and in vivo antiviral activities. J.Med.Chem. 32 1442 PMID: 2544721
Hou et al (2013) Pluripotent stem cells induced from mouse somatic cells by small-molecule compounds. Science 341 651 PMID: 23868920
If you know of a relevant reference for 3-Deazaneplanocin A hydrochloride, please let us know.
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Keywords: 3-Deazaneplanocin A hydrochloride, 3-Deazaneplanocin A hydrochloride supplier, 3-DeazaneplanocinA, NSC617989, Histone, methylation, inhibitors, inhibits, EZH2, trimethylation, apoptosis, s-adenosylhomocysteine, hydrolase, SAHH, CiPSCs, stem, cells, reprogramming, induced, pluripotent, pluripotency, PRC2, polycomb, repressive, complex, 2, DZNep, NSC, 617989, Stem, Cell, Reprogramming, Lysine, Methyltransferases, 4703, Tocris Bioscience
4 Citations for 3-Deazaneplanocin A hydrochloride
Citations are publications that use Tocris products. Selected citations for 3-Deazaneplanocin A hydrochloride include:
Wang et al (2017) Using low-risk factors to generate non-integrated human induced pluripotent stem cells from urine-derived cells. Stem Cell Res Ther 8 245 PMID: 29096702
Stefan et al (2016) Histone Demethylation and Toll-like Receptor 8-Dependent Cross-Talk in Monocytes Promotes Transdifferentiation of Fibroblasts in Systemic Sclerosis Via Fra-2. Arthritis Rheumatol 68 1493-504 PMID: 26814616
Jerzy et al (2017) The role of microRNA-5196 in the pathogenesis of systemic sclerosis. Eur J Clin Invest 47 555-564 PMID: 28639412
Ping et al (2018) Genome-wide DNA methylation analysis reveals that mouse chemical iPSCs have closer epigenetic features to mESCs than OSKM-integrated iPSCs. Cell Death Dis 9 187 PMID: 29416007
Do you know of a great paper that uses 3-Deazaneplanocin A hydrochloride from Tocris? Please let us know.
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Protocols for 3-Deazaneplanocin A hydrochloride
The following protocol features additional information for the use of 3-Deazaneplanocin A hydrochloride (Cat. No. 4703).
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.
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.
Stem Cells Scientific Review
Written by Kirsty E. Clarke, Victoria B. Christie, Andy Whiting and Stefan A. Przyborski, this review provides an overview of the use of small molecules in the control of stem cell growth and differentiation. Key signaling pathways are highlighted, and the regulation of ES cell self-renewal and somatic cell reprogramming is discussed. Compounds available from Tocris are listed.
Cancer Metabolism Poster
This poster summarizes the main metabolic pathways in cancer cells and highlights potential targets for cancer therapeutics. Genetic changes and epigenetic modifications in cancer cells alter the regulation of cellular metabolic pathways providing potential cancer therapeutic targets.
Epigenetics in Cancer Poster
This poster summarizes the main epigenetic targets in cancer. The dysregulation of epigenetic modifications has been shown to result in oncogenesis and cancer progression. Unlike genetic mutations, epigenetic alterations are considered to be reversible and thus make promising therapeutic targets.
Stem Cells Poster
Written by Rebecca Quelch and Stefan Przyborski from Durham University (UK), this poster describes the isolation of pluripotent stem cells, their maintenance in culture, differentiation, and the generation and potential uses of organoids.