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5.06069

3-Deazaneplanocin A hydrochloride

Name: 3-Deazaneplanocin A hydrochloride
Brand: MM

InSolution, ≥98%, 25 mM aqueous solution, EZH2 Inhibitor

Synonym(s):

InSolution EZH2 Inhibitor, DZNep, 3-Deazaneplanocin A, xHCl, yH₂O {x = 3 & y = 2}, (1S,2R,5R)-5-(4-Amino-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol, xHCl, yH₂O {x = 3 & y = 2}, NSC 617989

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₁₄N₄O₃ · 3HCl · 2H₂O

CAS Number:

102052-95-9

Molecular Weight:

407.68

MDL number:

MFCD17779310

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

liquid

Storage condition:

OK to freeze, avoid repeated freeze/thaw cycles, protect from light

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Properties

Quality Segment

100

assay

≥98% (HPLC)

form

liquid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, avoid repeated freeze/thaw cycles, protect from light

storage temp.

−70°C

SMILES string

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

InChI

1S/C12H14N4O3/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)/t8-,10-,11+/m1/s1

InChI key

OMKHWTRUYNAGFG-IEBDPFPHSA-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.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
EZH2

Reversible: yes

Packaging

Packaged under inert gas

Physical form

A 25 mM (1 mg/98 µL) sterile-filtered solution of Histone Methyltransferase EZH2 Inhibitor, DZNep (Cat. No. 252790) in H₂O.

Preparation Note

Following initial thaw, aliquot and freeze (-20°C). Aliquots are stable for up to 6 monthst at -20°C.

This product is a 25 mM (1 mg/98 µL) sterile-filtered solution in H₂O.

Other Notes

Sun, F., et al. 2009. Mol. Cancer Ther.8, 3191.
Miranda, T.B., et al. 2009. Mol. Cancer Ther.8, 1579.
Fiscus, W., et al. 2009. Blood13, 2733.
Tan, J., et al. 2007. Genes Dev.21, 1050.
Chiang, P.K., et al. 1992. J. Biol. Chem.267, 4988.
Tseng, C.K., et al. 1989. J. Med. Chem.32, 1442.
Glazer, R.I., et al. 1986. Biochem. Biophys. Res. Commun.135, 688.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

12 - Non Combustible Liquids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c