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8-pCPT-2'-O-Me-cAMP-AM

8- (4- Chlorophenylthio)- 2'- O- methyladenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( 8-pCPT-2'-O-Me-cAMP-AM )
Metabolically activatable, highly membrane-permeant Epac agonist
Cat. No.: C 051
    
CAS No.: [1152197-23-3]
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Product Name Price (net) Qty
Cat. No.: C 051-01
Unit: 1 µmol / ~0.6 mg
$187.00

Extremely membrane-permeant precursor of the specific Epac agonist 8-pCPT-2'-O-Me-cAMP (Cat. No. C 041). After permeation and metabolic activation by esterases the active compound 8-pCPT-2'-O-Me-cAMP is released. References: Vliem et al., ChemBioChem9, 2052 - 2054 (2008); Chepurny et al., J. Biol. Chem., 284, 10728 - 10736 (2009); Chepurny et al., Am. J.Physiol., 298, E622 - E633 (2010).

Related products: Biolog also offers Phosphate tris(acetoxymethyl)ester (PO4-AM3, Cat. No. P 030) which is recommended as control reagent in nucleotide-AM ester applications. 6-Bnz-cAMP-AM (Cat. No. B 079) is a highly membrane-permeant specific activator of PKA and can be used as Epac-negative control.

Cat. No. C 051
Patent Information Protected by patent n° EP 02077219.0 and foreign equivalents, exclusively licensed to BIOLOG LSI for research purposes only
CAS number [1152197-23-3]
Purity > 97% HPLC for mixture of isomers
Storage temperature -20°C / -4°F
Molecular formula C₂₀H₂₁ClN₅O₈PS
Molecular weight [g/mol] 557.9
Modifications 8-cAMP, 2'-cAMP
Target Epac Activator
Absorption max [nm] 282
Molar extinction coefficient ε [L·mol⁻¹·cm⁻¹] 16000
  • 1. Henquin J.-C.Nenquin M., Endocrinol., 0, 0 - 0 (2014), "Activators of PKA and Epac Distinctly Influence Insulin Secretion and Cytosolic Ca2+ in Female Mouse Islets Stimulated by Glucose and Tolbutamide"
  • 2. Almahariq M., Tsalkova T., Mei F. C., Chen H., Zhou J., Sastry S. K., Schwede F.Cheng X., Mol. Pharmacol., 83, 122 - 128 (2013), "A Novel EPAC Specific Inhibitor Suppresses Pancreatic Cancer Cell Migration and Invasion"
  • 3. Pannekoek W.-J., Linnemann J. R., Brouwer P. M., Bos J. L.Rehmann H., PLoS ONE, 8(2), 0, 0 - 0 (2013), "Rap1 and Rap2 Antagonistically Control Endothelial Barrier Resistance"
  • 4. Chepurny O. G., Bertinetti D., Diskar M., Leech C. A., Afshari P., Tsalkova T., Cheng X., Schwede F., Genieser H.-G., Herberg F. W.Holz G. G., Mol. Endocrinol., 27, 1267 - 1282 (2013), "Stimulation of Proglucagon Gene Expression by Human GPR119 in Enteroendocrine L-cell Line GLUTag"
  • 5. Takahashi T., Shibasaki T., Takahashi H., Sugawara K., Ono A., Inoue N., Furuya T.Seino S., Sci. Signal., 6(298), 0, 0 - 0 (2013), "Antidiabetic Sulfonylurease and cAMP Cooperatively Activate Epac2A"
  • 6. Tsalkova T., Mei F. C.Cheng X., PloS ONE, 7, 0 - 0 (2012), "A Fluorescence-Based High-Throughout Assay for the Discovery of Exchange Protein Directly Activated by cyclic AMP (Epac) Antagonists"
  • 7. Dzhura I., Chepurny O. G., Leech C. A., Roe M. W., Dzhura E., Xu X., Lu Y., Schwede F., Genieser H.-G., Smrcka A. V.Holz G. G., Islets, 3, 121 - 128 (2011), "Phospholipase C-epsilon Links Epac2 Activation to the Potentiation of Glucose-stimulated Insulin Secretion from Mouse Islets of Langerhans"
  • 8. Holz G. G., Chepurny O. G., Leech C. A., Dzhura I., Kelley G. G., Roe W. R., Dzhura E., Li X., Schwede F.Genieser H.-G., Biophys. J., 98, 680 - 680 (2010), "A Permissive Role for Protein Kinase A in Support of Epac Agonist-Stimulated Human Islet Insulin Secretion"
  • 9. Leech C. A., Dzhura I., Chepurny O. G., Schwede F., Genieser H.-G.Holz G. G., Islets, 2, 72 - 81 (2010), "Facilitation of beta-cell KATP Channel Sulfonylurea Sensivity by a cAMP Analog Selective for the cAMP-regulated Guanine Nucleotide Exchange Factor Epac"
  • 10. Idevall-Hagren O., Barg S., Gylfe E.Tengholm A., J. Biol. Chem., 285, 23007 - 23018 (2010), "cAMP Mediators of Pulsatile Insulin Secretion from Glucose-stimulated Single Beta-cells"
  • 11. Chepurny O. G., Kelley G. G., Dzhura I., Leech C. A., Roe M. W., Dzhura E., Li X., Schwede F., Genieser H.-G.Holz G. G., Am. J. Physiol.-Endocrinol. Metabol., 298, 622 - 633 (2010), "PKA-dependent Potentiation of Glucose-stimulated Insulin Secretion by Epac Activator 8-pCPT-2'-O-Me-cAMP-AM in Human Islets of Langerhans"
  • 12. Gerlo S., Verdood P.Kooijman R., J. Interferon Cytokine Res., 30, 883 - 891 (2010), "Modulation of Cytokine Production by Cyclic Adenosine Monophosphate Analogs in Human Leukocytes"
  • 13. Dzhura I., Chepurny O. G., Kelley G. G., Leech C. A., Roe M. W., Dzhura E., Afshari P., Malik S., Rindler M. J., Xu X., Lu Y., Smrcka A. V.Holz G. G., J. Physiol., 588, 4871 - 4889 (2010), "EPAC2-dependent Mobilization of Intracellular Ca2+ by Glucagon-like Peptide-1 Receptor Agonist Exendin-4 is Disrupted in Beta-Cells of Phospholipase C-Epsilon Knockout Mice"
  • 14. Gaudy A. M., Clementi A. H., Campbell J. S., Smrcka A. V.Mooney R. A., J. Biol. Chem., 285, 41356 - 41365 (2010), "Supressor of Cytokine Signaling-3 is a Glucagon-Inducible Inhibitor of PKA Activity and Gluconeogenic Gene Expression in Hepatocytes"
  • 15. Chepurny O. G., Leech C. A., Kelley G. G., Dzhura I., Dzhura E., Li X., Rindler M. J., Schwede F., Genieser H.-G.Holz G. G., J. Biol. Chem., 284, 10728 - 10736 (2009), "Enhanced Rap1 activation and insulin secretagogue properties of an acetoxymethyl ester of an Epac-selective cyclic AMP analog in rat INS-1 cells: Studies with 8-pCPT-2'-O-Me-cAMP-AM."
  • 16. Kelley G. G., Chepurny O. G., Schwede F., Genieser H.-G., Leech C. A., Roe M. W., Li X., Dzhura I., Dzhura E., Afshari P.Holz G. G., Islets, 1, 260 - 265 (2009), "Glucose-dependent Potentation of Mouse Islet Insulin Secretion by Epac Activator 8-pCPT-2'-O-Me-cAMP-AM"
  • 17. Vliem M. J., Ponsioen B., Schwede F., Pannekoek W.-J., Riedl J., Kooistra M. R. H., Jalink K., Genieser H.-G., Bos J. L.Rehmann H., ChemBioChem, 9, 2052 - 2054 (2008), "8-pCPT-2'-O-Me-cAMP-AM: An Improved Epac-selective cAMP Analogue"