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252790

3-Deazaneplanocin A hydrochloride

Name: 3-Deazaneplanocin A hydrochloride
Brand: MM

≥97% (HPLC), solid, EZH2 inhibitor, Calbiochem^®

Synonym(s):

Histone Methyltransferase EZH2 Inhibitor, DZNep, 3-deazaneplanocin A, HCl; (1S,2R,5R)-5-(4-amino-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol, HCl, HMTase Inhibitor X

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₁₄N₄O₃ · xHCl · yH₂O

CAS Number:

120964-45-6

Molecular Weight:

262.26 (anhydrous free base basis)

UNSPSC Code:

12352200

NACRES:

NA.77

MDL number:

MFCD18782644

Assay:

≥97% (HPLC)

Form:

solid

Storage condition:

OK to freeze, desiccated (hygroscopic), protect from light

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Properties

Product Name

Histone Methyltransferase EZH2 Inhibitor, DZNep, Histone Methyltransferase EZH2 Inhibitor, DZNep, CAS 120964-45-6, is a cell-permeable inhibitor of EZH2-mediated trimethylation of K27 on histone H3.

Quality Segment

100

assay

≥97% (HPLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, desiccated (hygroscopic), protect from light

color

tan

solubility

DMSO: 10 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

Cl.[n]2(c3c(nc2)c(ncc3)N)[C@H]1[C@@H]([C@@H](C(=C1)CO)O)O

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/t8-,10-,11+;/m1./s1

InChI key

UNSKMHKAFPRFTI-FDKLLANESA-N

Description

General description

A cell-permeable compound that is shown (at 1 µM concentrations) to inhibit EZH2-mediated trimethylation of K27 on histone H3 and induces the expression of cell-cycle regulatory genes, p21 and p27, as well as the cell death regulator, FBXO32, in OCI-AML3 and HL-60 cells, whereby treatment with inhibitor increases p16 levels in the former, but not the latter of the two cultures. At concentrations between 200 nm and 2000 nM, this compound is found to dose-dependently deplete the expression of polycomb group proteins EZH2, SUZ12, and EED in cultured and primary AML cell extracts. At concentrations up to ≥ 1000 nM, DZNep dose-dependently increases the percentage of apoptotic cells up to > ~ 38%, with greater potency against OCI-AML3 than HL-60 cultures and inhibits colony growth up to > ~ 85% for both cell lines. In OCI-AML3 cultures, 1000 nM of treatment demonstrates a significant increase in the accumulation of cells in the G₀/G₁ phase (58.5%) with a concomitant decrease in the number of cells in S phase (35.2%) and G₂/M phases (6.3%) of the cell cycle. When co-treated with panobinostat (PS), 200 nM to 1000nM DZNep is shown to decrease cell viability in OCI-AML3 and HL-60 cultures more effectively than DZNep alone, in a dose-dependent manner. DZNep (1mg/kg, twice per week, i.p.) and PS significantly prolong the survival of mice implanted with HL-60 cells compared to treatment with either compound alone. DZNep is also a known S-adenosyl-L-homocysteine (AdoHcy) hydrolase inhibitor. Also available as a 25 mM solution in H₂O (Cat. No. 506069).

Packaging

Packaged under inert gas

Physical form

Supplied as a hydrochloride salt.

Preparation Note

Following reconstitution, aliquot and freeze 9-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Fiscus, W., et al. 2009. Blood13, 2733.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c