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SML0305

Sigma-Aldrich

3-Deazaneplanocin A hydrochloride

≥97% (HPLC)

Sinonimo/i:

(-)-1-[(1R,4R,5S)-3-(Hydroxymethyl)-4,5-dihydroxy-2-cyclopenten-1-yl]4-aminoimidazo[4,5-c]pyridine hydrochloride, DZNep hydrochloride

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About This Item

Formula empirica (notazione di Hill):
C12H14N4O3 · HCl
Numero CAS:
120964-45-6
Peso molecolare:
298.73
Numero MDL:
MFCD18782644
Codice UNSPSC:
12352200
ID PubChem:
329825310
NACRES:
NA.77

Saggio

≥97% (HPLC)

Forma fisica

powder

Attività ottica

[α]/D -88 to -108°, c = 0.1 in water

Condizioni di stoccaggio

desiccated

Colore

white to beige

Solubilità

H2O: ≥5 mg/mL

Condizioni di spedizione

wet ice

Temperatura di conservazione

−20°C

Stringa SMILE

Cl.Nc1nccc2n(cnc12)[C@@H]3C=C(CO)[C@@H](O)[C@H]3O

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
UNSKMHKAFPRFTI-FDKLLANESA-N

Descrizione generale

3-Deazaneplanocin A hydrochloride is a carbocyclic analog of adenosine. It has antimetastatic property. It is used to treat Ebola virus disease, gastric cancer, myeloma and lymphoma.

Applicazioni

3-Deazaneplanocin A hydrochloride has been used to examine the potential involvement of autophagy and apoptosis in colorectal cancer (CRC) cells.
3-Deazaneplanocin A hydrochloride has been used to test its effect on ovarian tumor progression. It has also been used as a S-adenosyl homocysteine hydrolase (SAH) inhibitor in c33A2 cells.

Azioni biochim/fisiol

3-Deazaneplanocin A (DZNep) is an S-Adenosylhomocysteine Hydrolase inhibitor and histone methyltransferase EZH2 inhibitor. It switches on repressed tumor suppressor genes and induces apoptosis by inhibiting the expression of EZH2.

Caratteristiche e vantaggi

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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Song-Hee Kim et al.
Biomolecules, 11(4) (2021-05-01)
EPHA3, a member of the EPH family, is overexpressed in various cancers. We demonstrated previously that EPHA3 is associated with radiation resistance in head and neck cancer via the PTEN/Akt/EMT pathway; the inhibition of EPHA3 significantly enhances the efficacy of
3-Deazaneplanocin A (DZNep), an inhibitor of S-adenosylmethionine-dependent methyltransferase, promotes erythroid differentiation
Fujiwara T, et al.
The Journal of Biological Chemistry, 289(12), 8121-8134 (2014)
Epigenetic silencing of T H 1-type chemokines shapes tumour immunity and immunotherapy
Peng D, et al.
Nature, 527(7577), 249-249 (2015)
3-Deazaneplanocin A (DZNep), an inhibitor of the histone methyltransferase EZH2, induces apoptosis and reduces cell migration in chondrosarcoma cells
Girard N, et al.
Testing, 9(5), e98176-e98176 (2014)
Chengfa Zhao et al.
Reproduction (Cambridge, England), 157(4), 359-369 (2019-02-08)
Somatic cell nuclear transfer in mammalian cloning suffers from a faulty epigenetic reprogramming, which is believed to cause developmental failures in cloned embryos. Regulating the epigenetic-modifying enzymes can rescue the chromatin of cloned embryos from aberrant epigenetic status, thereby potentially
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