A stable ATP analog and P2X1,3 agonist
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α,β-Methyleneadenosine 5'-triphosphate (sodium salt)

Item No. 10008956

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5'-[hydrogen P-[[hydroxy(phosphonooxy)phosphinyl]methyl]phosphonate] adenosine, trisodium salt
CAS Number
1343364-54-4
Synonyms
  • αβ-methylene ATP
Molecular Formula
C11H15N5O12P3 • 3Na
Formula Weight
571.2
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
λmax
259 nm
SMILES
O[C@H]1[C@@H](O)[C@H](N2C=NC3=C2N=CN=C3N)O[C@@H]1COP(CP(OP(O)([O-])=O)([O-])=O)([O-])=O.[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C11H18N5O12P3.3Na/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(27-11)1-26-29(19,20)4-30(21,22)28-31(23,24)25;;;/h2-3,5,7-8,11,17-18H,1,4H2,(H,19,20)(H,21,22)(H2,12,13,14)(H2,23,24,25);;;/q;3*+1/p-3/t5-,7-,8-,11-;;;/m1.../s1
InChi Key
CBAGKCWFSRTVER-MTQUBGKESA-K
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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    Product Description

    α,β-Methyleneadenosine 5'-triphosphate (αβ-methylene ATP) is a phosphonic analog of ATP that is characterized by the replacement of the bridging oxygen atom between the α- and β-phosphate groups with methylene. It is an agonist of P2X purinoceptors P2X1 and P2X3 (EC50 = ~1 µM) and is ~1,000-fold less potent at P2X2, P2X receptors 4-7, and P2Y receptors.1,2,3,4 Persistent activation of purinoceptors results in desensitization, resulting in an antagonist-like effect of αβ-methylene ATP.5 αβ-methylene ATP is used as a stable analog of ATP (Item No. 14498) to study the interaction of ATP with kinases and other proteins.6,7 It weakly binds and inhibits adenylate cyclase in a calcium-dependent manner (Ki= ~0.5 mM).8,9

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. North, R.A. Molecular physiology of P2X receptors. Physiol. Rev. 82(4), 1013-1067 (2002).

    2. Coddou, C., Yan, Z., Obsil, T., et al. Activation and regulation of purinergic P2X receptor channels. Pharmacol. Rev. 63(3), 641-683 (2011).

    3. Helms, N., Kowalski, M., Illes, P., et al. Agonist antagonist interactions at the rapidly desensitizing P2X3 receptor. PLoS One 8(11), 1-11 (2013).

    4. Abbracchio, M.P., Burnstock, G., Boeynaems, J.M., et al. International Union of Pharmacology LVIII: Update on the P2Y G protein-coupled nucleotide receptors: From molecular mechanisms and pathophysiology to therapy. Pharmacol. Rev. 58(3), 281-341 (2006).

    5. Dunn, P.M. Fertility: Purinergic receptors and the male contraceptive pill. Curr. Biol. 10(8), R305-R307 (2000).

    6. Gibson, K.J., Schubert, K.R., and Switzer, R.L. Binding of the substrates and the allosteric inhibitor adenosine 5'-diphosphate to phosphoribosylpyrophosphate synthetase from Salmonella typhimurium. The Journal of Biological Chemisty 257(5), 2391-2396 (1982).

    7. Steegborn, C., Litvin, T.N., Levin, L.R., et al. Bicarbonate activation of adenylyl cyclase via promotion of catalytic active site closure and metal recruitment. Nat. Struct. Mol. Biol. 12(1), 32-37 (2005).

    8. Krug, F., Parikh, I., Illiano, G., et al. αβ-Methylene-adenosine 5'-triphosphate. A competitive inhibitor of adenylate cyclase in fat and liver cell membranes. The Journal of Biological Chemisty 248(4), 1203-1206 (1973).

    9. Dessauer, C.W., Scully, T.T., and Gilman, A.G. Interactions of forskolin and ATP with the cytosolic domains of mammalian adenylyl cyclase. The Journal of Biological Chemisty 272(35), 22272-22277 (1997).