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SML0305

Sigma-Aldrich

3-Deazaneplanocin A hydrochloride

≥97% (HPLC)

Sinônimo(s):

(-)-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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1 MG
R$ 3.489,00
5 MG
R$ 11.663,00

About This Item

Fórmula empírica (Notação de Hill):
C12H14N4O3 · HCl
Número CAS:
Peso molecular:
298.73
Número MDL:
Código UNSPSC:
12352200
ID de substância PubChem:
NACRES:
NA.77

R$ 3.489,00


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Ensaio

≥97% (HPLC)

Formulário

powder

atividade óptica

[α]/D -88 to -108°, c = 0.1 in water

condição de armazenamento

desiccated

cor

white to beige

solubilidade

H2O: ≥5 mg/mL

Condições de expedição

wet ice

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

UNSKMHKAFPRFTI-FDKLLANESA-N

Descrição geral

3-Deazaneplanocin A hydrochloride is a carbocyclic analog of adenosine. It has antimetastatic property.[1] It is used to treat Ebola virus disease,[2] gastric cancer, myeloma and lymphoma.[3]

Aplicação

3-Deazaneplanocin A hydrochloride has been used to examine the potential involvement of autophagy and apoptosis in colorectal cancer (CRC) cells.[4]
3-Deazaneplanocin A hydrochloride has been used to test its effect on ovarian tumor progression.[5] It has also been used as a S-adenosyl homocysteine hydrolase (SAH) inhibitor in c33A2 cells.[6]

Ações bioquímicas/fisiológicas

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.
3-Deazaneplanocin A is an S-Adenosylhomocysteine Hydrolase inhibitor and histone methyltransferase EZH2 inhibitor.

Características e benefícios

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable


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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)
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
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
Downregulation of enhancer of Zeste Homolog 2 (EZH2) is essential for the induction of autophagy and apoptosis in colorectal cancer cells
Yao Y, et al.
Genes, 7(10), 83-83 (2016)
3-Deazaneplanocin A induces massively increased interferon-alpha production in Ebola virus-infected mice
Bray M, et al.
Antiviral research, 55(1), 151-159 (2002)

Artigos

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

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