3-Deazaneplanocin A

{{Chembox

| ImageFile = 3-Deazaneplanocin A.svg

| ImageSize = 200px

| ImageAlt =

| PIN = (1S,2R,5R)-5-(6-Amino-9H-purin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo = 102052-95-9

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 544SH4020S

| PubChem = 73087

| ChemSpiderID = 65874

| SMILES = n3ccc1c(ncn1[C@@H]2/C=C(/CO)[C@@H](O)[C@H]2O)c3N

| 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

| InChIKey = OMKHWTRUYNAGFG-IEBDPFPHBD

| StdInChI = 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

| StdInChIKey = OMKHWTRUYNAGFG-IEBDPFPHSA-N }}

|Section2={{Chembox Properties

| Formula = C₁₂H₁₄N₄O₃

| MolarMass = 262.265

| Appearance =

| Density =

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|Section3={{Chembox Hazards

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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.{{cite journal|last=Glazer|first=R.I.|author2=Knode, M.C.|author3=Tseng, C.K.|author4=Haines, D.R.|author5=Marquez, V.E.|year=1986|title=3-Deazaneplanocin A: a new inhibitor of S-adenosylhomocysteine synthesis and its effects in human colon carcinoma cells|journal=Biochemical Pharmacology|publisher=Elsevier|volume=35|issue=24|pages=4523–7|doi=10.1016/0006-2952(86)90774-4 |pmid=3790170|url=https://zenodo.org/record/1253814}}{{cite journal|last1=Fiskus|first1=W.|last2=Wang|first2=Y.|last3=Sreekumar|first3=A.|last4=Buckley|first4=K. M.|last5=Shi|first5=H.|last6=Jillella|first6=A.|last7=Ustun|first7=C.|last8=Rao|first8=R.|last9=Fernandez|first9=P.|last10=Chen|first10=J.|last11=Balusu|first11=R.|last12=Koul|first12=S.|last13=Atadja|first13=P.|last14=Marquez|first14=V. E.|last15=Bhalla|first15=K. N.|title=Combined epigenetic therapy with the histone methyltransferase EZH2 inhibitor 3-deazaneplanocin A and the histone deacetylase inhibitor panobinostat against human AML cells|journal=Blood|volume=114|issue=13|year=2009|pages=2733–2743|pmid=19638619|pmc=2756128|doi=10.1182/blood-2009-03-213496}}{{cite journal|last1=Kikuchi|first1=Junko|last2=Takashina|first2=Taichi|last3=Kinoshita|first3=Ichiro|last4=Kikuchi|first4=Eiki|last5=Shimizu|first5=Yasushi|last6=Sakakibara-Konishi|first6=Jun|last7=Oizumi|first7=Satoshi|last8=Marquez|first8=Victor E.|last9=Nishimura|first9=Masaharu|last10=Dosaka-Akita|first10=Hirotoshi|title=Epigenetic therapy with 3-deazaneplanocin A, an inhibitor of the histone methyltransferase EZH2, inhibits growth of non-small cell lung cancer cells|journal=Lung Cancer|volume=78|issue=2|year=2012|pages=138–143|pmc=3472089|pmid=22925699|doi=10.1016/j.lungcan.2012.08.003}}{{cite journal|last=Liang|first=Shen|year=2013|title= 3-Deazaneplanocin A is a Promising Therapeutic Agent for Ovarian Cancer Cells |journal=Asian Pacific Journal of Cancer Prevention|volume=14|issue=5|issn=1513-7368}}{{cite journal|last1=Fujiwara|first1=T.|last2=Saitoh|first2=H.|last3=Inoue|first3=A.|last4=Kobayashi|first4=M.|last5=Okitsu|first5=Y.|last6=Katsuoka|first6=Y.|last7=Fukuhara|first7=N.|last8=Onishi|first8=Y.|last9=Ishizawa|first9=K.|last10=Ichinohasama|first10=R.|last11=Harigae|first11=H.|title=3-Deazaneplanocin A (DZNep), an Inhibitor of S-Adenosylmethionine-dependent Methyltransferase, Promotes Erythroid Differentiation|journal=Journal of Biological Chemistry|volume=289|issue=12|year=2014|pages=8121–8134|pmc=3961643|pmid=24492606|doi=10.1074/jbc.M114.548651|doi-access=free}}

In studies on mice, the drug was also found to be effective for the treatment of Ebola virus disease,{{cite journal | doi = 10.1086/514316| title = Antiviral Drug Therapy of Filovirus Infections: S-Adenosylhomocysteine Hydrolase Inhibitors Inhibit Ebola Virus in Vitro and in a Lethal Mouse Model| journal = The Journal of Infectious Diseases| volume = 179| pages = S240–7| year = 1999| last1 = Huggins | first1 = J. | last2 = Zhang | first2 = Z. X. | last3 = Bray | first3 = M. | pmid=9988190| doi-access = free}} apparently interfering with the Ebola viruses ability to block interferon production, thus restoring the ability of immune system to rid the body of ebolavirus.{{cite journal

| pmid = 12076759

| year = 2002

| last1 = Bray

| first1 = M

| title = 3-deazaneplanocin a induces massively increased interferon-alpha production in Ebola virus-infected mice

| journal = Antiviral Research

| volume = 55

| issue = 1

| pages = 151–9

| last2 = Raymond

| first2 = J. L.

| last3 = Geisbert

| first3 = T

| last4 = Baker

| first4 = R. O.

| doi=10.1016/s0166-3542(02)00018-9

| url = https://zenodo.org/record/1259873

}}{{cite journal

| pmid = 25246419

| pmc = 4216250

| year = 2014

| last1 = Shuchman

| first1 = M

| title = Could interferon help treat Ebola?

| journal = Canadian Medical Association Journal

| doi = 10.1503/cmaj.109-4906

| volume=186

| issue = 16

| pages=1204

}}