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Merck

Z4775

Zebularine

≥98% (HPLC), cytidine analogue, 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
UNSPSC Code:
12352203
PubChem Substance ID:
329831617
NACRES:
NA.77
MDL number:
MFCD04973699
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100

Key Documents

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Product Name

Zebularine, ≥98% (HPLC), solid

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

assay

≥98% (HPLC)

form

solid

solubility

DMSO: 16 mg/mL

storage temp.

2-8°C

Quality Level

100

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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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000233911
0000233911
0000182000
0000156430

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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
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
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
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)
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
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