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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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5 MG

R 2,604.84

25 MG

R 10,413.48

R 2,604.84

List PriceR 2,658.00
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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

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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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1 of 4

This Item
691400D8296SML2310
Zebularine ≥98% (HPLC), solid

Sigma-Aldrich

Z4775

Zebularine

Zebularine A cell-permeable chemically stable cytidine analog that displays antitumor properties.

Sigma-Aldrich

691400

Zebularine

3-Deazaadenosine

Sigma-Aldrich

D8296

3-Deazaadenosine

Thiodigalactoside ≥98% (HPLC)

Sigma-Aldrich

SML2310

Thiodigalactoside

assay

≥98% (HPLC)

assay

≥95% (HPLC)

assay

-

assay

≥98% (HPLC)

form

solid

form

solid

form

powder

form

powder

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

solubility

DMSO: 16 mg/mL

solubility

DMSO: 5 mg/mL, methanol: 5 mg/mL

solubility

-

solubility

H2O: 2 mg/mL, clear

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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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
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
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
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
View All Related Papers

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We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Carcinogenesis and Epigenetics

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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