An adenine nucleotide and ATP analog
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2-Chloroadenosine 5-triphosphate (sodium salt)

Item No. 34978

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-chloro-adenosine 5′-(tetrahydrogen triphosphate), tetrasodium salt
CAS Number
301334-89-4
Synonyms
  • 2-chloro ATP
Molecular Formula
C10H11ClN5O13P3 • 4Na
Formula Weight
629.6
Purity
≥95%
Formulation (Request formulation change)
A 10 mM solution in water
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
O[C@H]1[C@](O[C@@H]([C@H]1O)COP(OP(OP([O-])([O-])=O)([O-])=O)([O-])=O)([H])N2C3=NC(Cl)=NC(N)=C3N=C2.[Na+].[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C10H15ClN5O13P3.4Na/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(18)5(17)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21;;;;/h2-3,5-6,9,17-18H,1H2,(H,22,23)(H,24,25)(H2,12,14,15)(H2,19,20,21);;;;/q;4*+1/p-4/t3-,5-,6-,9-;;;;/m1..../s1
InChi Key
JGKMWMQAWOVZHJ-ZVQJTLEUSA-J
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    1 mg

    $110

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    2.7 mg

    $283

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    Product Description

    2-Chloroadenosine 5-triphosphate (2-chloro ATP) is an adenine nucleotide and analog of ATP (Item No. 14498).1,2 It is an antagonist of the purinergic P2Y1 receptor, inhibiting intracellular calcium mobilization induced by ADP (Item No. 21121) in Jurkat cells expressing the human receptor (Ki = 2.3 µM).3 2-chloro ATP is an agonist of purinergic P2X receptors, inducing inward currents in HEK293 cells expressing the human bladder smooth muscle or rat PC12 forms of the receptor (EC50s = 0.5 and 2.5 µM, respectively).4 It induces relaxation of precontracted isolated guinea pig taenia caeci strips in a concentration-dependent manner.1 It has been used to study the substrate specificity of cyclic nucleotide-dependent protein kinases, such as protein kinase A (PKA) and PKG.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Satchell, G., and Maguire, M.H. Inhibitory effects of adenine nucleotide analogs on the isolated guinea-pig taenia coli. J. Pharmacol. Exp. Ther. 195(3), 540-548 (1975).

    2. Flockhart, D.A., Freist, W., Hoppe, J.O., et al. ATP analog specificity of CAMP-dependent protein kinase, cGMP-dependent protein kinase, and phosphorylase kinase. Eur. J. Biochem. 140(2), 289-295 (1984).

    3. Hechler, B., Vigne, P., Léon, C., et al. ATP derivatives are antagonists of the P2Y1 receptor: Similarities to the platelet ADP receptor. Mol. Pharmacol. 53(4), 727-733 (1997).

    4. Evans, R.J., Lewis, C., Buell, G., et al. Pharmacological characterization of heterologously expressed ATP-gated cation channels (P2x purinoceptors). Mol. Pharmacol. 48(2), 178-183 (1995).