3-Deazaneplanocin A (CAS 102052-95-9) | Cayman Chemical
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3-Deazaneplanocin A

Item № 13828
CAS № 102052-95-9
Purity ≥97%
product image
                (CAS 102052-95-9)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     500 µg $79.00 0.00
     1 mg $142.00 0.00
     5 mg $395.00 0.00
     10 mg $569.00 0.00

Pricing updated 2019-01-16. Prices are subject to change without notice.

Description
Synonyms
  • DZNep
  • NSC 617989

The lysine methyltransferase EZH2 (KMT6), part of the polycomb repressive complex 2, catalyzes trimethylation of lysine 27 on histone H3 and is involved in proliferation and aggressive cell growth associated with neoplastic cells.1 3-Deazaneplanocin A is a cyclopentenyl analog of 3-deazaadenosine, originally synthesized as an inhibitor of S-adenosyl-L-homocysteine hydrolase.2 It has been shown to deplete EZH2 levels and to inhibit trimethylation of lysine 27 on histone H3 in cultured human acute myeloid leukemia (AML) HL-60 and OCI-AML3 cells and in primary AML cells in a dose-dependent manner (0.2-1 μM).3 3-Deazaneplanocin A treatment of cultured human AML cells induces increased expression of the cell-cycle regulators p21, p27, and FBXO32, leading to cell cycle arrest and apoptosis.3 When used in combination with the pan-histone deacetylase inhibitor panobinostat (10 mg/kg), 3-deazaneplanocin A’s (1 mg/kg) antileukemic effects are synergistically enhanced in mice implanted with AML cells.3,4

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Technical Information
Formal Name
5R-(4-amino-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)-3-cyclopentene-1S,2R-diol
CAS Number
102052-95-9
Synonyms
  • DZNep
  • NSC 617989
Molecular Formula
C12H14N4O3
Formula Weight
262.3
Purity
≥97%
Formulation
A crystalline solid
λmax
268 nm
SMILES
NC1=NC=CC2=C1N=CN2[C@H]3[C@H](O)[C@H](O)C(CC)=C3
InChI Code
InChI=1S/2C12H14N4O3/c2*13-12-9-7(1-2-14-12)16(5-15-9)8-3-6(4-17)10(18)11(8)19/h2*1-3,5,8,10-11,17-19H,4H2,(H2,13,14)/t8-,10+,11-;8-,10-,11+/m01/s1
InChI Key
FNYLTRHIFUEEJP-XISHOVGXSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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References & Product Citations
Product Description References

1. Simon, J.A., and Lange, C.A. Roles of the EZH2 histone methyltransferase in cancer epigenetics Mutation Research 647, 21-29 (2008).

2. Tseng, C.K.H., Marquez, V.E., Fuller, R.W., et al. Synthesis of 3-deazaneplanocin A, a powerful inhibitor of S-adenosylhomocysteine hydrolase with potent and selective in vitro and in vivo antiviral activities Journal of Medicinal Chemistry 32, 1442-1446 (1989).

3. Fiskus, W., Wang, Y., Sreekumar, A., et al. Combined epigenetic therapy with the histone methyltransferase EZH2 inhibitor 3-deazaneplanocin A and the histone deacetylase inhibitor panobinostat against human AML cells Blood 114(13), 2733-2743 (2009).

4. Bissinger, E.M., Heinke, R., Sippl, W., et al. Targeting epigenetic modifiers: Inhibitors of histone methyltransferases Med.Chem.Commun. (2010).

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