3-Deazaneplanocin A hydrochloride

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Cat.No. 4703 - 3-Deazaneplanocin A hydrochloride | C12H14N4O3.HCl | CAS No. 120964-45-6
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)
Datasheet
Citations (1)
Reviews
Protocols (1)
Literature

Biological Activity

Histone methyltransferase inhibitor; decreases global histone methylation. 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. 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).

Technical Data

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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
water 2.99 10

Preparing Stock Solutions

The following data is based on the product molecular weight 298.73. Batch specific molecular weights may vary from batch to batch due to solvent 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 3.35 mL 16.74 mL 33.48 mL
5 mM 0.67 mL 3.35 mL 6.7 mL
10 mM 0.33 mL 1.67 mL 3.35 mL
50 mM 0.07 mL 0.33 mL 0.67 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

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


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1 Citation 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


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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* or download your copy today!

*Please note that Tocris will only send literature to established scientific business / institute addresses.


Epigenetics

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

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.

Epigenetics

Epigenetics Research Bulletin

Produced by Tocris and updated in 2014, the epigenetics research bulletin gives an introduction into mechanisms of epigenetic regulation, and highlights key Tocris products for epigenetics targets including:

  • Bromodomains
  • DNA Methyltransferases
  • Histone Deacetylases
  • Histone Demethylases
  • Histone Methyltransferases
Cancer Metabolism

Cancer Metabolism Poster

Adapted from the 2015 Cancer Product Guide, Edition 3, this poster summarizes the main targets for cancer metabolism researchers. Genetic changes and epigenetic modifications in cancer cells alter the regulation of cellular metabolic pathways. These distinct metabolic circuits could provide viable cancer therapeutic targets.

Epigenetics in Cancer

Epigenetics in Cancer Poster

Adapted from the 2015 Cancer Product Guide Edition 3, 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

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.