A nucleoside analog and an ADAR1 inhibitor
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8-Azaadenosine

Item No. 34622

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-β-D-ribofuranosyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-amine
CAS Number
10299-44-2
Synonyms
  • NSC 72961
Molecular Formula
C9H12N6O4
Formula Weight
268.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 5 mg/mlDMSO:PBS (pH 7.2) (1:4): 0.20 mg/ml
λmax
280 nm
SMILES
O[C@H]1[C@](O[C@@H]([C@H]1O)CO)([H])N2C3=NC=NC(N)=C3N=N2
InChi Code
InChI=1S/C9H12N6O4/c10-7-4-8(12-2-11-7)15(14-13-4)9-6(18)5(17)3(1-16)19-9/h2-3,5-6,9,16-18H,1H2,(H2,10,11,12)/t3-,5-,6-,9-/m1/s1
InChi Key
OAUKGFJQZRGECT-UUOKFMHZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    25 mg

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    Cayman Chemical
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    Product Description

    8-Azaadenosine is a purine nucleoside analog and an inhibitor of adenosine deaminase acting on RNA 1 (ADAR1), an enzyme that converts adenosine to inosine in dsRNA, a post-transcriptional modification known as A-to-I editing.1 It inhibits RNA A-to-I editing in, as well as the invasion and migration of, TPC-1 and Cal-62 thyroid cancer cells when used at concentrations of 1 and 2 µM. 8-Azaadenosine (2 mg/kg) increases the ex vivo secretion of IFN-γ and TNF-α from CD8+ T cells isolated from mouse spleen in a model of hepatitis B virus (HBV) infection.2 It decreases serum levels of HBV surface antigen (HBsAg) in the same model.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ramírez-Moya, J., Baker, A.R., Slack, F.J., et al. ADAR1-mediated RNA editing is a novel oncogenic process in thyroid cancer and regulates miR-200 activity. Oncogene 39(18), 3738-3753 (2020).

    2. Wang, L., Sun, Y., Song, X., et al. Hepatitis B virus evades immune recognition via RNA adenosine deaminase ADAR1-mediated viral RNA editing in hepatocytes. Cell Mol. Immunol. 18(8), 1781-1882 (2021).