3-Deazaneplanocin A

3-Deazaneplanocin A
Names
	Preferred IUPAC name (1S,2R,5R)-5-(6-Amino-9H-purin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol
Identifiers
CAS Number	102052-95-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	65874;
ECHA InfoCard	100.224.238
PubChem CID	73087;
UNII	544SH4020S ;
CompTox Dashboard (EPA)	DTXSID30144562 ;
	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 Key: OMKHWTRUYNAGFG-IEBDPFPHSA-N; InChI=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/s1 Key: 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

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]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

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[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.

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