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Merck

SML0305

3-Deazaneplanocin A hydrochloride

≥97% (HPLC), S-adenosylhomocysteine hydrolase inhibitor, powder

Synonyme(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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A propos de cet article

Formule empirique (notation de Hill) :
C12H14N4O3 · HCl
Numéro CAS:
120964-45-6
Poids moléculaire :
298.73
UNSPSC Code:
12352200
PubChem Substance ID:
329825310
NACRES:
NA.77
MDL number:
MFCD18782644
Assay:
≥97% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated

Principaux documents

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Nom du produit

3-Deazaneplanocin A hydrochloride, ≥97% (HPLC)

SMILES string

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

InChI key

UNSKMHKAFPRFTI-FDKLLANESA-N

assay

≥97% (HPLC)

form

powder

optical activity

[α]/D -88 to -108°, c = 0.1 in water

storage condition

desiccated

color

white to beige

solubility

H2O: ≥5 mg/mL

shipped in

wet ice

storage temp.

−20°C

Quality Level

100

Catégories apparentées

General description

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.

Application

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.

Biochem/physiol Actions

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.

Features and Benefits

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.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000216956
0000216957
0000206982
0000206982
0000216957

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Consulter la Bibliothèque de documents

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)
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
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)
Anna Nowicka et al.
The Plant journal : for cell and molecular biology, 102(1), 68-84 (2019-11-17)
Repetitive DNA sequences and some genes are epigenetically repressed by transcriptional gene silencing (TGS). When genetic mutants are not available or problematic to use, TGS can be suppressed by chemical inhibitors. However, informed use of epigenetic inhibitors is partially hampered
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