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Z4775

Sigma-Aldrich

Zebularine

≥98% (HPLC), solid

Synonyme(s) :

1-(β-D-Ribofuranosyl)-1,2-dihydropyrimidin-2-one, 2-Pyrimidone-1-β-D-riboside

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About This Item

Formule empirique (notation de Hill):
C9H12N2O5
Numéro CAS:
3690-10-6
Poids moléculaire :
228.20
Numéro MDL:
MFCD04973699
Code UNSPSC :
12352203
ID de substance PubChem :
329831617
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

solid

Solubilité

DMSO: 16 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=CC=NC2=O

InChI

1S/C9H12N2O5/c12-4-5-6(13)7(14)8(16-5)11-3-1-2-10-9(11)15/h1-3,5-8,12-14H,4H2/t5-,6-,7-,8-/m1/s1

Clé InChI

RPQZTTQVRYEKCR-WCTZXXKLSA-N

Actions biochimiques/physiologiques

Zebularine is a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent.

Caractéristiques et avantages

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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C B Yoo et al.
Biochemical Society transactions, 32(Pt 6), 910-912 (2004-10-28)
Regulatory genes are often hypermethylated at their promoter 5' regions and silenced in cancer. Epigenetic therapy with DNA methylation inhibitors have been shown to result in the demethylation and reactivation of these genes. Zebularine is a recently discovered mechanism-based inhibitor
Yan Li et al.
eLife, 9 (2020-05-28)
Circadian oscillations are generated via transcriptional-translational negative feedback loops. However, individual cells from fibroblast cell lines have heterogeneous rhythms, oscillating independently and with different period lengths. Here we showed that heterogeneity in circadian period is heritable and used a multi-omics
Fatima Ismail Hassan et al.
Current pharmaceutical design, 24(24), 2862-2869 (2018-09-05)
Sepsis is among the leading causes of death with no specific etiology or treatment. Increase in health burden in terms of cost, morbidity, and mortality is the reason behind the continuous search for different treatment modalities which involve several targets/approach
Mariana Díaz et al.
The Plant cell, 31(7), 1579-1597 (2019-05-01)
The maintenance of genome integrity over cell divisions is critical for plant development and the correct transmission of genetic information to the progeny. A key factor involved in this process is the STRUCTURAL MAINTENANCE OF CHROMOSOME5 (SMC5) and SMC6 (SMC5/6)
Yukitoshi Takemura et al.
Bioscience, biotechnology, and biochemistry, 82(7), 1159-1164 (2018-04-25)
Malignant mesothelioma is an asbestos-related aggressive tumor and current therapy remains ineffective. Zebularine as a DNA methyltransferase (DNMT) inhibitor has an anti-tumor effect in several human cancer cells. The aim of the present study was to investigate whether zebularine could
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