A non-hydrolyzable analog of cAMP
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Rp-Cyclic AMPS (triethylammonium salt)

Item No. 16985

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclic 3',5'-[hydrogen (R)-phosphorothioate] adenosine, triethylammonium salt
CAS Number
151837-09-1
Synonyms
  • Rp-cAMPS
Molecular Formula
C10H11N5O5PS • C6H16N
Formula Weight
446.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 10 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
260 nm
SMILES
O[C@H]1[C@H](N2C=NC3=C2N=CN=C3N)O[C@H]4[C@H]1O[P@@](OC4)([S-])=O.CC[NH+](CC)CC
InChi Code
InChI=1S/C10H12N5O5PS.C6H15N/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(19-10)1-18-21(17,22)20-7;1-4-7(5-2)6-3/h2-4,6-7,10,16H,1H2,(H,17,22)(H2,11,12,13);4-6H2,1-3H3/t4-,6-,7-,10-,21-;/m1./s1
InChi Key
OXIPZMKSNMRTIV-RNSTXJOVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Rp-Cyclic AMPS (Rp-cAMPS) is a non-hydrolyzable phosphorothioate analog of cAMP.1 It is a competitive inhibitor of cAMP-dependent protein kinases I and II (IC50s = 12.5 and 4.5 µM, respectively).2,3 Rp-cAMPS is not hydrolyzed by bovine heart cAMP phosphodiesterase but can be hydrolyzed by yeast phosphodiesterase.4 It is broadly used in research involving cAMP-dependent signaling in vitro and in vivo.1,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schaap, P., van Ments-Cohen, M., Soede, R.D., et al. Cell-permeable non-hydrolyzable cAMP derivatives as tools for analysis of signaling pathways controlling gene regulation in Dictyostelium. The Journal of Biological Chemisty 268(9), 6323-6331 (1993).

    2. De Wit, R.J.W., Hekstra, D., Jastorff, B., et al. Inhibitory action of certain cyclophosphate derivatives of cAMP on cAMP-dependent protein kinases. Eur. J. Biochem. 142(2), 255-260 (1984).

    3. Van Haastert, P.J.M., van Driel, R., Jastorff, B., et al. Competitive cAMP antagonists for cAMP-receptor proteins. The Journal of Biological Chemisty 259(16), 10020-10024 (1984).

    4. Jarvest, R.L., Lowe, G., Baraniak, J., et al. A stereochemical investigation of the hydrolysis of cyclic AMP and the (Sp)-and (Rp)-diastereoisomers of adenosine cyclic 3':5'-phosphorothioate by bovine heart and baker’s-yeast cyclic AMP phosphodiesterases. Biochem. J. 203(2), 461-470 (1982).

    5. Schwede, F., Maronde, F., Genieser, H., et al. Cyclic nucleotide analogs as biochemical tools and prospective drugs. Pharmacol. Ther. 87(2), 199-226 (2000).

    6. Yokozaki, H., Tortora, G., Pepe, S., et al. Unhydrolyzable analogues of adenosine 3':5'-monophosphate demonstrating growth inhibition and differentiation in human cancer cells. Cancer Res. 52(9), 2504-2508 (1992).