3-deazaneplanocin A | CAS#120964-45-6 | CAS#102052-95-9 | EZH2 inhibitor

3-deazaneplanocin A HCl
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 406378

CAS#: 120964-45-6 (HCl)

Description: 3-deazaneplanocin A, also known as DZNep, is a well-known histone methyltransferase inhibitor, which disrupts polycomb-repressive complex 2 (PRC2), and induces apoptosis, while inhibiting proliferation and metastasis, in cancer cells, including acute myeloid leukemia, breast cancer and glioblastoma. DZNep is a promising therapeutic agent for ovarian cancer cells, with potential to inhibit proliferation, induce apoptosis and decrease migration.

Chemical Structure

3-deazaneplanocin A HCl

CAS# 120964-45-6 (HCl)

Instruction

Theoretical Analysis

MedKoo Cat#: 406378
Name: 3-deazaneplanocin A HCl
CAS#: 120964-45-6 (HCl)
Chemical Formula: C12H15ClN4O3
Exact Mass: 262.11
Molecular Weight: 298.727
Elemental Analysis: C, 48.25; H, 5.06; Cl, 11.87; N, 18.76; O, 16.07

Price and Availability

Size	Price	Availability
1mg	USD 395	2 Weeks
5mg	USD 1150	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 102052-95-9 (free base) 120964-45-6 (HCl)

Synonym: 3-deazaneplanocin A HCl; 3-deazaneplanocin A hydrochloride; DZNep; NSC 617989.

IUPAC/Chemical Name: (1S,2R,5R)-5-(4-amino-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol hydrochloride

InChi Key: UNSKMHKAFPRFTI-FDKLLANESA-N

InChi Code: 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

SMILES Code: O[C@@H]1[C@H](O)C(CO)=C[C@H]1N2C=NC3=C2C=CN=C3N.[H]Cl

Appearance: white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in water at 10mM.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in water or aqueous buffer.

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 298.73 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Tanaka R, Donovan N, Yu Q, Irie R, Hoon DS. Tumor Necrosis Factor-Alpha and Apoptosis Induction in Melanoma Cells through Histone Modification by 3-Deazaneplanocin A. J Invest Dermatol. 2013 Nov 13. doi: 10.1038/jid.2013.489. [Epub ahead of print] PubMed PMID: 24226421.

2: Shen L, Cui J, Pang YX, Ma YH, Liu PS. 3-Deazaneplanocin A is a Promising Therapeutic Agent for Ovarian Cancer Cells. Asian Pac J Cancer Prev. 2013;14(5):2915-8. PubMed PMID: 23803053.

3: Tam EK, Li Z, Goh YL, Cheng X, Wong SY, Santhanakrishnan S, Chai CL, Yao SQ. Cell-based proteome profiling using an affinity-based probe (AfBP) derived from 3-deazaneplanocin A (DzNep). Chem Asian J. 2013 Aug;8(8):1818-28. doi: 10.1002/asia.201300303. Epub 2013 Jun 7. PubMed PMID: 23749335.

4: Peer CJ, Rao M, Spencer SD, Shahbazi S, Steeg PS, Schrump DS, Figg WD. A rapid ultra HPLC-MS/MS method for the quantitation and pharmacokinetic analysis of 3-deazaneplanocin A in mice. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 May 15;927:142-6. doi: 10.1016/j.jchromb.2013.01.003. Epub 2013 Jan 9. PubMed PMID: 23352636; PubMed Central PMCID: PMC3640617.

5: Kikuchi J, Takashina T, Kinoshita I, Kikuchi E, Shimizu Y, Sakakibara-Konishi J, Oizumi S, Marquez VE, Nishimura M, Dosaka-Akita H. 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. doi: 10.1016/j.lungcan.2012.08.003. Epub 2012 Aug 25. PubMed PMID: 22925699; PubMed Central PMCID: PMC3472089.

6: Cheng LL, Itahana Y, Lei ZD, Chia NY, Wu Y, Yu Y, Zhang SL, Thike AA, Pandey A, Rozen S, Voorhoeve PM, Yu Q, Tan PH, Bay BH, Itahana K, Tan P. TP53 genomic status regulates sensitivity of gastric cancer cells to the histone methylation inhibitor 3-deazaneplanocin A (DZNep). Clin Cancer Res. 2012 Aug 1;18(15):4201-12. doi: 10.1158/1078-0432.CCR-12-0036. Epub 2012 Jun 6. PubMed PMID: 22675170.

7: Avan A, Crea F, Paolicchi E, Funel N, Galvani E, Marquez VE, Honeywell RJ, Danesi R, Peters GJ, Giovannetti 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. doi: 10.1158/1535-7163.MCT-12-0037. Epub 2012 May 23. PubMed PMID: 22622284; PubMed Central PMCID: PMC3416916.

8: Sun F, Li J, Yu Q, Chan E. 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. doi: 10.1016/j.ejpb.2011.10.014. Epub 2011 Oct 28. PubMed PMID: 22061261.

9: "Epigenetically reprogramming of human embryonic stem cells by 3-deazaneplanocin A and sodium butyrate", Int J Prev Med. 2011 Apr;2(2):73-8 is retracted. Int J Prev Med. 2011 Jul;2(3):187. PubMed PMID: 21811663; PubMed Central PMCID: PMC3143534.

10: Chiba T, Suzuki E, Negishi M, Saraya A, Miyagi S, Konuma T, Tanaka S, Tada M, Kanai F, Imazeki F, Iwama A, Yokosuka O. 3-Deazaneplanocin A is a promising therapeutic agent for the eradication of tumor-initiating hepatocellular carcinoma cells. Int J Cancer. 2012 Jun 1;130(11):2557-67. doi: 10.1002/ijc.26264. Epub 2011 Aug 20. PubMed PMID: 21717453.

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