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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
MDL number:
MFCD04973699
UNSPSC Code:
12352203
PubChem Substance ID:
329831617
NACRES:
NA.77

Key Documents

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Product Name

Zebularine, ≥98% (HPLC), solid

Quality Level

100

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

Related Categories

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)

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Certificates of Analysis (COA)

Lot/Batch Number
0000233911
0000233911
0000182000
0000156430

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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
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
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
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
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Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.

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