3-deazaneplanocin A HCl

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 406378

CAS#: 120964-45-6

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.


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3-deazaneplanocin A HCl, purity > 98%, is not in stock, may be available through custom synthesis. Minimum 1 gram order is requested. Current shipping out time is about 70 days after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 406378
Name: 3-deazaneplanocin A HCl
CAS#: 120964-45-6
Chemical Formula: C12H15ClN4O3
Exact Mass: 262.10659
Molecular Weight: 298.727
Elemental Analysis: C, 48.25; H, 5.06; Cl, 11.87; N, 18.76; O, 16.07


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


Technical Data

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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

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.