3-Deazaneplanocin A hydrochloride (DZNep), Lysine methyltransferase EZH2 inhibitor

Key facts

Purity

>98%

Form

Solid

form

Molecular weight

298.72 Da

Molecular formula

C₁₂H₁₅ClN₄O₃

PubChem

358176

Nature

Synthetic

Solubility

Soluble in water to 10 mM

Soluble in DMSO to 10 mM

Biochemical name

3-Deazaneplanocin hydrochloride

Biological description

Lysine methyltransferase EZH2 inhibitor. Competitive s-adenosylhomocysteine hydrolase inhibitor (K_i = 50 pM). DZNep acts as an epigenetic modifier, specifically blocking trimethylation of lysine 27 on histone H3 and lysine 20 on histone H4. (Miranda et al., Tan et al., Tseng et al.) Induces cancer cell selective apoptosis. Adenosine (ab120498) analog. Inhibits self-renewal of glioblastoma multiforme cancer stem cells (Suva et al.).
Inhibits survival of acute myeloid leukemia blast cells, in combination with a histone deacetylase inhibitor (Fiskus et al.). Enables chemical reprogramming of mouse embryonic fibroblasts iPSC, in combination with CHIR99021 (ab120890), Forskolin (ab120058), Valproic Acid (ab120745), Tranylcypromine (ab120606) and E-616452 (ab142139), by increasing OCT4 expression at later stages of reprogramming (Hou et al.).

Canonical smiles

C1=CN=C(C2=C1N(C=N2)C3C=C(C(C3O)O)CO)N.Cl

InChi

InChI=1S/C12H14N4O3.ClH/c13-12-9-7(1-2-14-12)16(5-15-9)8-3-6(4-17)10(18)11(8)19;/h1-3,5,8,10-11,17-19H,4H2,(H2,13,14);1H

InChiKey

UNSKMHKAFPRFTI-UHFFFAOYSA-N

IUPAC Name

5-(4-aminoimidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol;hydrochloride