A selective super-activator of Epacs
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8-pCPT-2'-O-methyl Cyclic AMP

Item No. 17143

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8-[(4-chlorophenyl)thio]-2'-O-methyl-adenosine cyclic 3',5'-(hydrogen phosphate), monosodium salt
CAS Number
634207-53-7
Synonyms
  • 8-CPT-2-methyl cAMP
  • 8-CPT-2-methyl Cyclic adenosine monophosphate
  • 8-pCPT cAMP
  • 8-pCPT Cyclic adenosine monophosphate
  • 8-pCPT Cyclic AMP
  • 8-pCPT-2'-O-methyl cAMP
  • 8-pCPT-2'-O-methyl Cyclic adenosine monophosphate
Molecular Formula
C17H16N5O6ClPS • Na
Formula Weight
507.8
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
210, 224, 283 nm
SMILES
O=P1([O-])O[C@H]2[C@@H](OC)[C@H](N3C(SC4=CC=C(Cl)C=C4)=NC5=C3N=CN=C5N)O[C@@H]2CO1.[Na+]
InChi Code
InChI=1S/C17H17ClN5O6PS.Na/c1-26-13-12-10(6-27-30(24,25)29-12)28-16(13)23-15-11(14(19)20-7-21-15)22-17(23)31-9-4-2-8(18)3-5-9;/h2-5,7,10,12-13,16H,6H2,1H3,(H,24,25)(H2,19,20,21);/q;+1/p-1/t10-,12-,13-,16-;/m1./s1
InChi Key
VHTMKTNUXDACHB-KHXPSBENSA-M
License
Protected by Patent No. EP 02077219.0 and foreign equivalents. Exclusively licensed to BIOLOG Life Science Institute for research purposes only.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $125

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    1 mg

    $236

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    5 mg

    $988

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    Product Description

    8-pCPT-2’-O-methyl Cyclic AMP (8-pCPT-2′-O-Me-cAMP) is an 8-(4-chlorophenylthio) analog of cAMP that activates Epacs (AC50 = 1.8 µM).1 It is a super-activator of Epacs in that it dissociates GDP from Rap1 more strongly than the natural Epac agonist, cAMP.1,2 8-pCPT-2′-O-Me-cAMP is strongly selective for Epac over the cAMP-activated kinase PKA.2 It does not discriminate between Epac1 and Epac2 and is used extensively to elucidate the roles of these Rap GEFs in cell function.3,4,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rehmann, H., Schwede, F., Doskeland, S.O., et al. Ligand-mediated activation of the cAMP-responsive guanine nucleotide exchange factor Epac. The Journal of Biological Chemisty 278(40), 38548-38556 (2003).

    2. Christensen, A.E., Selheim, F., de Rooij, J., et al. cAMP analog mapping of Epac1 and cAMP kinase. Discriminating analogs demonstrate that Epac and cAMP kinase act synergistically to promote PC-12 cell neurite extension. The Journal of Biological Chemisty 278(37), 35394-35402 (2003).

    3. Breckler, M., Berthouze, M., Laurent, A.C., et al. Rap-linked cAMP signaling Epac proteins: Compartmentation, functioning and disease implications. Cell. Signal. 23(8), 1257-1266 (2011).

    4. Kang, G., Chepurny, O.G., Malester, B., et al. cAMP sensor Epac as a determinant of ATP-sensitive potassium channel activity in human pancreatic β cells and rat INS-1 cells. J. Physiol. 573(Pt 3), 595-609 (2006).

    5. Eid, A.H., Chotani, M.A., Mitra, S., et al. Cyclic AMP acts through Rap1 and JNK signaling to increase expression of cutaneous smooth muscle α2C-adrenoceptors. Am. J. Physiol. Heart Circ. Physiol. 295(1), H266-H272 (2008).

    6. Quan, Y., Jiang, J., and Dingledine, R. EP2 receptor signaling pathways regulate classical activation of microglia. The Journal of Biological Chemisty 288(13), 9293-9302 (2013).