3-Deazaneplanocin A (DZNep) hydrochlorideSAHH and ENZ2 inhibitor CAS# 120964-45-6 |
- 3-Deazaneplanocin,DZNep
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Quality Control & MSDS
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| Cas No. | 120964-45-6 | SDF | Download SDF |
| PubChem ID | 14563109 | Appearance | Powder |
| Formula | C12H15ClN4O3 | M.Wt | 298.73 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | DZNep hydrochloride; NSC 617989 hydrochloride; 3-Deazaneplanocin hydrochloride | ||
| Solubility | H2O : 50 mg/mL (167.38 mM; Need ultrasonic) | ||
| Chemical Name | (1S,2R,5R)-5-(4-aminoimidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol;hydrochloride | ||
| SMILES | C1=CN=C(C2=C1N(C=N2)C3C=C(C(C3O)O)CO)N.Cl | ||
| Standard InChIKey | UNSKMHKAFPRFTI-FDKLLANESA-N | ||
| Standard 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/t8-,10-,11+;/m1./s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 3-Deazaneplanocin A hydrochloride is an inhibitor of histone methyltransferase. | |||||
| Targets | histone methyltransferase | |||||
| Cell experiment:[1] | |
| Cell lines | Human acute myeloid leukemia (AML) cell |
| Preparation method | The solubility of this compound in DMSO is >10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while.Stock solution can be stored below -20°C for several months. |
| Reacting condition | 100-750 nM; 24-72h |
| Applications | DZNep induced apoptosis in cultured and primary AML cells. DZNep exhausted EZH2 levels, and inhibits trimethylation of lysine 27 on histone H3 in the AML HL-60 and OCI-AML3 cells. DZNep induced the levels of p16, p21, p27, and FBXO32 after cyclin E and HOXA9 levels run out. |
| Animal experiment:[2] | |
| Animal models
| Sprague-Dawley rats (120–140 g) |
| Dosage form
| 5μM DZNep for 24 h pre-treatment before experiment, orally taken with diets |
| Application | DZNep significantly reduced EZH2 expression and activity, and it increased lipid accumulation, inflammatory molecules and microRNAs in non-alcoholic fatty liver disease (NAFLD) mouse model. |
| Other notes
| Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
| References: 1. Fiskus W1, 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. 2009 Sep 24;114(13):2733-43. 2. Vella S, Gnani D, Crudele A et al. EZH2 down-regulation exacerbates lipid accumulation and inflammation in vitro and in vivo NAFLD.Int J Mol Sci. 2013 Dec 12;14(12):24154-68. | |
3-Deazaneplanocin A (DZNep) hydrochloride Dilution Calculator
3-Deazaneplanocin A (DZNep) hydrochloride Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.3475 mL | 16.7375 mL | 33.475 mL | 66.9501 mL | 83.6876 mL |
| 5 mM | 0.6695 mL | 3.3475 mL | 6.695 mL | 13.39 mL | 16.7375 mL |
| 10 mM | 0.3348 mL | 1.6738 mL | 3.3475 mL | 6.695 mL | 8.3688 mL |
| 50 mM | 0.067 mL | 0.3348 mL | 0.6695 mL | 1.339 mL | 1.6738 mL |
| 100 mM | 0.0335 mL | 0.1674 mL | 0.3348 mL | 0.6695 mL | 0.8369 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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3-Deazaneplanocin A (DZNep) hydrochloride is a selective inhibitor of ENZ2 inhibitor with IC50 value of 0.08-0.24 μM [1].
ENZ2 is a sub-unit of PRC2 and plays an important role in regulating cell proliferation and cell-cycle progression. It has been reported that ENZ2 is over-expressed in many tumors, including prostate, breast, bladder cancers and AML [2]. In HepG2 cell lines, DZNep treatment markedly induced the intracellular lipids increasement and TNF-αand TGF-βexpression in mRNA level by augmenting PA/OA-dependent lipid accumulation [3].
DZNep is a potent ENZ2 inhibitor. When tested with human acute myeloid leukemia (AML) HL-60 and OCI-AML3 cell lines, administration of DZNep induced cell apoptosis by depleting ENZ2, cyclin E and HOXA9 expressions and inducing p16, p21,p27 and FBXO32 expressions in a dose-dependent manner [2].
In high-fat/high-fructose diet fed (HFa/HFr-D) rat mouse model that resembles human NAFLD metabolically and histologically, DZNep functioned as the effective agent to anti-inflammatory and anti-fibrotic roles by inhibiting ENZ2 [3].
It is also reported that DZNep has the inhibitory activity for (SAHH (S-adenosylhomocysteine hydrolase) with Ki value of 50 pM [4].
References:
[1]. Kikuchi, J., et al., 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. 78(2): p. 138-43.
[2]. Fiskus, W., 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, 2009. 114(13): p. 2733-43.
[3]. Vella, S., et al., EZH2 down-regulation exacerbates lipid accumulation and inflammation in in vitro and in vivo NAFLD. Int J Mol Sci, 2013. 14(12): p. 24154-68.
[4]. Glazer, R.I., et al., 3-Deazaneplanocin A: a new inhibitor of S-adenosylhomocysteine synthesis and its effects in human colon carcinoma cells. Biochem Pharmacol, 1986. 35(24): p. 4523-7.
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Epigenetic Modifications with DZNep, NaBu and SAHA in Luminal and Mesenchymal-like Breast Cancer Subtype Cells.[Pubmed:27365379]
Cancer Genomics Proteomics. 2016 Jul-Aug;13(4):291-303.
BACKGROUND/AIM: Numerous studies have shown that breast cancer and epigenetic mechanisms have a very powerful interactive relation. The MCF7 cell line, representative of luminal subtype and the MDA-MB 231 cell line representative of mesenchymal-like subtype were treated respectively with a Histone Methyl Transferase Inhibitors (HMTi), 3-Deazaneplanocin hydrochloride (DZNep), two histone deacetylase inhibitors (HDACi), sodium butyrate (NaBu), and suberoylanilide hydroxamic acid (SAHA) for 48 h. MATERIALS AND METHODS: Chromatin immunoprecipitation (ChIP) was used to observe HDACis (SAHA and NaBu) and HMTi (DZNep) impact on histones and more specifically on H3K27me3, H3K9ac and H3K4ac marks with Q-PCR analysis of BRCA1, SRC3 and P300 genes. Furthermore, the HDACi and HMTi effects on mRNA and protein expression of BRCA1, SRC3 and P300 genes were checked. In addition, statistical analyses were used. RESULTS: In the MCF7 luminal subtype with positive ER, H3k4ac was significantly increased on BRCA1 with SAHA. On the contrary, in the MDA-MB 231 breast cancer cell line, representative of mesenchymal-like subtype with negative estrogen receptor, HDACis had no effect. Also, DZNEP decreased significantly H3K27me3 on BRCA1 in MDA-MB 231. Besides, on SRC3, a significant increase for H3K4ac was obtained in MCF7 treated with SAHA. And DZNEP had no effect in MCF7. Also, in MDA-MB 231 treated with DZNEP, H3K27me3 significantly decreased on SRC3 while H3K4ac was significantly increased in MDA-MB-231 treated with SAHA or NaBu for P300. CONCLUSION: Luminal and mesenchymal-like breast cancer subtype cell lines seemed to act differently to HDACis (SAHA and NaBu) or HMTi (DZNEP) treatments.
