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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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)
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
Li Chen et al.
Frontiers in genetics, 9, 254-254 (2018-08-02)
Large-scale tumor genome sequencing projects have revealed a complex landscape of genomic mutations in multiple cancer types. A major goal of these projects is to characterize somatic mutations and discover cancer drivers, thereby providing important clues to uncover diagnostic or
Morgan Mosley et al.
Endocrinology, 158(6), 1838-1848 (2017-04-12)
Many of the best-studied neural sex differences relate to differences in cell number and are due to the hormonal control of developmental cell death. However, several prominent neural sex differences persist even if cell death is eliminated. We hypothesized that
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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