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Z4775

Sigma-Aldrich

Zebularine

≥98% (HPLC), solid

Sinónimos:

1-(β-D-Ribofuranosyl)-1,2-dihydropyrimidin-2-one, 2-Pyrimidone-1-β-D-riboside

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5 MG
$121.000
25 MG
$417.000

$121.000

Fecha estimada de envío20 de abril de 2025

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5 MG
$121.000
25 MG
$417.000

About This Item

Fórmula empírica (notación de Hill):
C9H12N2O5
Número de CAS:
3690-10-6
Peso molecular:
228.20
Número MDL:
MFCD04973699
Código UNSPSC:
12352203
ID de la sustancia en PubChem:
329831617
NACRES:
NA.77

$121.000

Fecha estimada de envío20 de abril de 2025

Solicitar un pedido a granel

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

solid

solubilidad

DMSO: 16 mg/mL

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

RPQZTTQVRYEKCR-WCTZXXKLSA-N

Acciones bioquímicas o fisiológicas

Zebularine is a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent.

Características y beneficios

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000182000
0000156430
0000182000
0000138661

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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
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
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
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
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