A PKA activator
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Sp-8-bromo-Cyclic AMPS (sodium salt)

Item No. 16002

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclic 3′,5′-[hydrogen [P(S)]-phosphorothioate]8-bromo-adenosine, monosodium salt
CAS Number
1573115-90-8
Synonyms
  • 8-Bromoadenosine 3',5'-cyclic Monophosphothioate SP-Isomer
  • Sp-8-bromo-cAMPS
Molecular Formula
C10H10BrN5O5PS • Na
Formula Weight
446.2
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 25 mg/mlEthanol: 0.5 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
212, 264 nm
SMILES
O[C@H]1[C@H](N2C(Br)=NC3=C2N=CN=C3N)O[C@H]4[C@H]1OP(OC4)([O-])=S.[Na+]
InChi Code
InChI=1S/C10H11BrN5O5PS.Na/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(20-9)1-19-22(18,23)21-6;/h2-3,5-6,9,17H,1H2,(H,18,23)(H2,12,13,14);/q;+1/p-1/t3-,5-,6-,9-,22?;/m1./s1
InChi Key
SKJLJCVVXRNYGJ-QKAIHBBZSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $129

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    1 mg

    $245

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    5 mg

    $825

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    Product Description

    Sp-8-bromo-cyclic AMPS (Sp-8-bromo-cAMPS) is a cell-permeable, cAMP analog that combines an exocyclic sulfur substitution in the axial position of the cyclophosphate ring with a bromine substitution in the adenine base of cAMP.1,2 This configuration pools the structural features of two established cyclic-AMP-dependent protein kinase (PKA) activators, 8-bromo-cAMP (Item No. 14431) and Sp-cAMPS (Item No. 14983). Sp-8-bromo-cAMPS is a PKA agonist (EC50 = 1.5 µM) with improved lipophilicity and is not readily degraded by cyclic nucleotide phosphodiesterases.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Dostmann, W.R., Taylor, S.S., Genieser, H.G., et al. Probing the cyclic nucleotide binding sites of cAMP-dependent protein kinases I and II with analogs of adenosine 3',5'-cyclic phosphorothioates. The Journal of Biological Chemisty 265(18), 10484-10491 (1990).

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

    4. 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).