3-Deazaneplanocin A


CAS No. : 102052-95-9

3-Deazaneplanocin A,102052-95-9
Product Details
For research use only. Not Intended for Therapeutic Use!
Cat No:I000148
Synonyms:(1S,2R,5R)-5-(4-aminoimidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol
Molecular Formula:C₁₂H₁₄N₄O₃
Molecular Weight:262.26
Target:Histone Methyltransferase
IC50:0.08-0.24 μM(NSCLC cell) [2]
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Assay:≥97%
Appearance:A crystalline solid
Cat No:I000148
Cas No:102052-95-9
Product-Name:3-Deazaneplanocin A
MDL No:MFCD12545899
InChI: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
InChIKey:OMKHWTRUYNAGFG-IEBDPFPHSA-N
SMILES:C1=CN=C(C2=C1N(C=N2)C3C=C(C(C3O)O)CO)N

3-Deazaneplanocin A (DZNep) is an attractive epigenetic anticancer agent through the inhibition of the cellular enhancer of zeste homolog 2 (EZH2) protein.
IC50 Value: 0.08-0.24 μM(NSCLC cell) [2]
Target: EZH2
in vitro: The 3-deazaneplanocin A (DZNeP; 5 μmol/L, 72-hour exposure) modulated EZH2 and H3K27me3 protein expression and synergistically enhanced the antiproliferative activity of gemcitabine, with combination index values of 0.2 (PANC-1), 0.3 (MIA-PaCa-2), and 0.7 (LPC006). The drug combination reduced the percentages of cells in G(2)-M phase (e.g., from 27% to 19% in PANC-1, P < 0.05) and significantly increased apoptosis compared with gemcitabine alone. Moreover, DZNeP enhanced the mRNA and protein expression of the nucleoside transporters hENT1/hCNT1, possibly because of the significant reduction of deoxynucleotide content (e.g., 25% reduction of deoxycytidine nucleotides in PANC-1), as detected by liquid chromatography/tandem mass spectrometry. DZNeP decreased cell migration, which was additionally reduced by DZNeP/gemcitabine combination (-20% in LPC006, after 8-hour exposure, P < 0.05) and associated with increased E-cadherin mRNA and protein expression. Furthermore, DZNeP and DZNeP/gemcitabine combination significantly reduced the volume of PDAC spheroids growing in CSC-selective medium and decreased the proportion of CD133+ cells [1]. MTT assays demonstrated that DZNep treatment resulted in dose-dependent inhibition of proliferation in the NSCLC cell lines with a half maximal inhibitory concentration (IC50) ranging from 0.08 to 0.24 μM [2].
in vivo: The pharmacokinetics of L-DZNep was investigated in Sprague-Dawley rats. In comparison with free drug, encapsulation of the DZNep in pegylated liposomes resulted in 99.3% reduction of the plasma clearance, whereas it increased the elimination half-life from 1.1 h to 8.0 h and the area under the plasma concentration curve by 138-fold [3].


[1]. Avan A, Crea F, Paolicchi E, Molecular mechanisms involved in the synergistic interaction of the EZH2 inhibitor 3-deazaneplanocin A with gemcitabine in pancreatic cancer cells. Mol Cancer Ther. 2012 Aug;11(8):1735-46.
[2]. Kikuchi J, Takashina T, Kinoshita I, Epigenetic therapy with 3-deazaneplanocin A, an inhibitor of the histone methyltransferase EZH2, inhibits growth of non-small cell lung cancer cells. Lung Cancer. 2012 Nov;78(2):138-43.
[3]. Sun F, Li J, Yu Q, Loading 3-deazaneplanocin A into pegylated unilamellar liposomes by forming transient phenylboronic acid-drug complex and its pharmacokinetic features in Sprague-Dawley rats. Eur J Pharm Biopharm. 2012 Feb;80(2):323-31.

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