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Z4775

Sigma-Aldrich

Zebularine

≥98% (HPLC), solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C9H12N2O5
CAS Number:
3690-10-6
Molecular Weight:
228.20
MDL number:
MFCD04973699
UNSPSC Code:
12352203
PubChem Substance ID:
329831617
NACRES:
NA.77

assay

≥98% (HPLC)

form

solid

solubility

DMSO: 16 mg/mL

storage temp.

2-8°C

SMILES string

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

InChI key

RPQZTTQVRYEKCR-WCTZXXKLSA-N

Biochem/physiol Actions

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

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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)
Victor E Marquez et al.
Annals of the New York Academy of Sciences, 1058, 246-254 (2006-01-06)
1-(Beta-d-ribofuranosyl)-1,2-dihydropyrimidin-2-one (zebularine) corresponds structurally to cytidine minus the exocyclic 4-amino group. The increased electrophilic character of its simple aglycon endows the molecule with unique biologic properties as a potent inhibitor of both cytidine deaminase and DNA cytosine methyltransferase. The latter
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