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MW 228.2 Da, Purity >99%. DNA methyltransferase( DNMT) inhibitor and cytidine deaminase inhibitor (Ki = 2 μM). Inhibits tumour growth in vitro and in vivo.

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Chemical Structure - Zebularine, DNA methyltransferase (DNMT) inhibitor (AB141264), expandable thumbnail

Key facts

CAS number
3690-10-6
Purity
> 99%
Form
Solid
Molecular weight
228.2 Da
Molecular formula
C9H12N2O5
PubChem identifier
100016
Nature
Synthetic

Alternative names

Recommended products

MW 228.2 Da, Purity >99%. DNA methyltransferase( DNMT) inhibitor and cytidine deaminase inhibitor (Ki = 2 μM). Inhibits tumour growth in vitro and in vivo.

Key facts

Purity
> 99%
PubChem identifier
100016
Solubility

Soluble in water to 100 mM.

Soluble in DMSO to 100 mM.

Biochemical name
Zebularine
Biological description

DNA methyltransferase( DNMT) inhibitor and cytidine deaminase inhibitor (Ki = 2 μM). Inhibits tumour growth in vitro and in vivo.

Canonical SMILES
C1=CN(C(=O)N=C1)C2C(C(C(O2)CO)O)O
Isomeric SMILES
C1=CN(C(=O)N=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
InChI
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
InChIKey
RPQZTTQVRYEKCR-WCTZXXKLSA-N
IUPAC name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one

Storage

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
+4°C
Appropriate long-term storage conditions
+4°C
Storage information
The product can be stored for up to 12 months

Supplementary info

This supplementary information is collated from multiple sources and compiled automatically.
Activity summary

Adenosine deaminase (ADA) sometimes known as deaminase is an enzyme that plays a critical mechanical role in cellular metabolism. This enzyme catalyzes the deamination of adenosine converting it into inosine. ADA is a 41 kDa protein primarily expressed in most tissues including the thymus and spleen. Various ADA assays and ADA protocols exist to study its functionality and quantification often using ADA ELISA kits to measure ADA activity in biological samples. In cell lines such as HeLa ADA expression is also present and significant for studying its regulation and function.

Biological function summary

Adenosine deaminase activity influences purine metabolism playing an important role in the breakdown of adenosine. It is not part of a complex but interacts closely with other components of the purine salvage pathway to maintain nucleotide balance. This enzyme is important for the proper function of immune cells as it prevents toxic accumulations of adenosine which can be detrimental to lymphocyte proliferation and function. ADA's activity ensures the proper management of nucleotides within cells sustaining cellular health and functionality.

Pathways

Adenosine deaminase plays significant roles in the immune and purine catabolism pathways. Within these pathways ADA is closely related to proteins such as purine nucleoside phosphorylase (PNP) which together orchestrate the steps necessary for adenine and guanine nucleotide turnover. These proteins facilitate the conversion processes needed for cellular nucleic acid synthesis and energy regulation. By managing adenosine levels ADA's function ensures the smooth operation of cellular signaling and metabolic balance.

Associated diseases and disorders

Adenosine deaminase deficiency is linked to severe combined immunodeficiency (SCID) and can also be associated with pulmonary disorders like asthma. A lack of ADA activity leads to the accumulation of toxic metabolites impairing immune function and contributing to the pathogenesis of SCID. In some patients with pulmonary disorders altered ADA activity impacts the inflammatory response. ADA's mechanistic interactions with other proteins such as PNP highlight its importance in maintaining immune competence and metabolic homeostasis emphasizing the enzyme's role in these clinical conditions.

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1 product image

  • Chemical Structure - Zebularine, DNA methyltransferase (DNMT) inhibitor (ab141264), expandable thumbnail

    Chemical Structure - Zebularine, DNA methyltransferase (DNMT) inhibitor (ab141264)

    2D chemical structure image of ab141264, Zebularine, DNA methyltransferase (DNMT) inhibitor

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Product protocols

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