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
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.

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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 products' biological activity.

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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Keywords: 3-DeazaneplanocinA NSC617989 Histone methylation inhibitors inhibits EZH2 trimethylation apoptosis s-adenosylhomocysteine hydrolase SAHH CiPSCs stem cells reprogramming induced pluripotent pluripotency DZNep NSC 617989 Lysine Methyltransferases

Citations for 3-Deazaneplanocin A hydrochloride

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Literature in this Area

Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
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.

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