3-Deazaneplanocin A (original) (raw)

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3-Deazaneplanocin A
Names
Preferred IUPAC name (1_S_,2_R_,5_R_)-5-(6-Amino-9_H_-purin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol
Identifiers
CAS Number 102052-95-9 checkY
3D model (JSmol) Interactive image
ChemSpider 65874
ECHA InfoCard 100.224.238 Edit this at Wikidata
PubChem CID 73087
UNII 544SH4020S checkY
CompTox Dashboard (EPA) DTXSID30144562 Edit this at Wikidata
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/s1Key: OMKHWTRUYNAGFG-IEBDPFPHSA-NInChI=1/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/s1Key: OMKHWTRUYNAGFG-IEBDPFPHBD
SMILES n3ccc1c(ncn1[C@@H]2/C=C(/CO)[C@@H](O)[C@H]2O)c3N
Properties
Chemical formula C12H14N4O3
Molar mass 262.265
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

3-Deazaneplanocin A (DZNep, C-c3Ado) is a drug which acts as both a _S_-adenosylhomocysteine synthesis inhibitor and also a histone methyltransferase EZH2 inhibitor. Studies have shown that it has effects in vitro against a variety of different tumor cell lines.[1][2][3][4][5]

In studies on mice, the drug was also found to be effective for the treatment of Ebola virus disease,[6] apparently interfering with the Ebola viruses ability to block interferon production, thus restoring the ability of immune system to rid the body of ebolavirus.[7][8]

  1. ^ Glazer, R.I.; Knode, M.C.; Tseng, C.K.; Haines, D.R.; Marquez, V.E. (1986). "3-Deazaneplanocin A: a new inhibitor of S-adenosylhomocysteine synthesis and its effects in human colon carcinoma cells". Biochemical Pharmacology. 35 (24). Elsevier: 4523–7. doi:10.1016/0006-2952(86)90774-4. PMID 3790170.
  2. ^ Fiskus, W.; Wang, Y.; Sreekumar, A.; Buckley, K. M.; Shi, H.; Jillella, A.; Ustun, C.; Rao, R.; Fernandez, P.; Chen, J.; Balusu, R.; Koul, S.; Atadja, P.; Marquez, V. E.; Bhalla, K. N. (2009). "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. doi:10.1182/blood-2009-03-213496. PMC 2756128. PMID 19638619.
  3. ^ Kikuchi, Junko; Takashina, Taichi; Kinoshita, Ichiro; Kikuchi, Eiki; Shimizu, Yasushi; Sakakibara-Konishi, Jun; Oizumi, Satoshi; Marquez, Victor E.; Nishimura, Masaharu; Dosaka-Akita, Hirotoshi (2012). "Epigenetic therapy with 3-deazaneplanocin A, an inhibitor of the histone methyltransferase EZH2, inhibits growth of non-small cell lung cancer cells". Lung Cancer. 78 (2): 138–143. doi:10.1016/j.lungcan.2012.08.003. PMC 3472089. PMID 22925699.
  4. ^ Liang, Shen (2013). "3-Deazaneplanocin A is a Promising Therapeutic Agent for Ovarian Cancer Cells". Asian Pacific Journal of Cancer Prevention. 14 (5). ISSN 1513-7368.
  5. ^ Fujiwara, T.; Saitoh, H.; Inoue, A.; Kobayashi, M.; Okitsu, Y.; Katsuoka, Y.; Fukuhara, N.; Onishi, Y.; Ishizawa, K.; Ichinohasama, R.; Harigae, H. (2014). "3-Deazaneplanocin A (DZNep), an Inhibitor of S-Adenosylmethionine-dependent Methyltransferase, Promotes Erythroid Differentiation". Journal of Biological Chemistry. 289 (12): 8121–8134. doi:10.1074/jbc.M114.548651. PMC 3961643. PMID 24492606.
  6. ^ Huggins, J.; Zhang, Z. X.; Bray, M. (1999). "Antiviral Drug Therapy of Filovirus Infections: S-Adenosylhomocysteine Hydrolase Inhibitors Inhibit Ebola Virus in Vitro and in a Lethal Mouse Model". The Journal of Infectious Diseases. 179: S240–7. doi:10.1086/514316. PMID 9988190.
  7. ^ Bray, M; Raymond, J. L.; Geisbert, T; Baker, R. O. (2002). "3-deazaneplanocin a induces massively increased interferon-alpha production in Ebola virus-infected mice". Antiviral Research. 55 (1): 151–9. doi:10.1016/s0166-3542(02)00018-9. PMID 12076759.
  8. ^ Shuchman, M (2014). "Could interferon help treat Ebola?". Canadian Medical Association Journal. 186 (16): 1204. doi:10.1503/cmaj.109-4906. PMC 4216250. PMID 25246419.