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:
Molecular Weight:
228.20
UNSPSC Code:
12352203
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
Zebularine, ≥98% (HPLC), solid
Quality Level
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.
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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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Takashi Akagi et al.
The Plant cell, 28(12), 2905-2915 (2016-12-14)
Epigenetic regulation can add a flexible layer to genetic variation, potentially enabling long-term but reversible cis-regulatory changes to an allele while maintaining its DNA sequence. Here, we present a case in which alternative epigenetic states lead to reversible sex determination
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
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