An inhibitor of ecto-5’-nucleotidase
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Adenosine 5'-methylenediphosphate (sodium salt)

Item No. 38359

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
adenosine, 5′-[hydrogen P-(phosphonomethyl)phosphonate], trisodium salt
CAS Number
2659222-76-9
Synonyms
  • Adenosine 5'-(α,β-methylene)diphosphate
  • AMP-CP
  • APCP
  • 5'-APCP
Molecular Formula
C11H14N5O9P2 • 3Na
Formula Weight
491.2
Purity
≥98%
Formulation (Request formulation change)
A 10 mM solution in water
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
O=P([O-])([O-])CP(OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(N)=C3N=C2)O1)([O-])=O.[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C11H17N5O9P2.3Na/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(25-11)1-24-27(22,23)4-26(19,20)21;;;/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H2,12,13,14)(H2,19,20,21);;;/q;3*+1/p-3/t5-,7-,8-,11-;;;/m1.../s1
InChi Key
HFZIEMSAEKBTDI-MTQUBGKESA-K
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    2.1 mg

    $112

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    Product Description

    Adenosine 5'-methylenediphosphate is an inhibitor of ecto-5’-nucleotidase, also known as CD73, with a Ki value of 37 nM.1 It inhibits cAMP accumulation induced by adenosine 5'-monophosphate (AMP; Item No. 21094), adenosine 5'-diphosphate (ADP; Item Nos. 16778 | 21121), or adenosine 5'-triphosphate (ATP; Item No. 14498), but not adenosine (Item No. 21232), in VA-13 human fibroblasts when used at a concentration of 100 µM. Adenosine 5'-methylenediphosphate reduces proliferation of U-138 MG glioma cells, as well as inhibits the invasion and migration of MHCC97H hepatocellular carcinoma (HCC) cells in a migration assay.2,3 It increases tumor infiltration of CD3+CD8+ T cells and reduces tumor growth in a K1735 murine melanoma model when administered at a dose of 400 µg/mouse.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bruns, R.F. Adenosine receptor activation by adenine nucleotides requires conversion of the nucleotides to adenosine. Naunyn Schmiedebergs Arch. Pharmacol. 315(1), 5-13 (1980).

    2. Braganhol, E., Tamajusuku, A.S.K., Bernardi, A., et al. Ecto-5′-nucleotidase/CD73 inhibition by quercetin in the human U138MG glioma cell line. Biochim. Biophys. Acta 1770(9), 1352-1359 (2007).

    3. Shali, S., Yu, J., Zhang, X., et al. Ecto‐5′‐nucleotidase (CD73) is a potential target of hepatocellular carcinoma. J. Cell Physiol. 234(7), 10248-10259 (2018).

    4. Forte, G., Sorrentino, R., Montinaro, A., et al. Inhibition of CD73 improves B cell-mediated anti-tumor immunity in a mouse model of melanoma. J. Immunol. 189(5), 2226-2233 (2021).