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Submit Review8-pCPT-2-O-Me-cAMP-AM
Description: Selective Epac activator; cell-permeable analog of 8CPT-2Me-cAMP (Cat. No. 1645)
Alternative Names: 007-AM
Chemical Name: 8-(4-Chlorophenylthio)-2'-O-methyladenosine-3',5'-cyclic monophosphate acetoxymethyl ester
Purity: ≥97% (HPLC)
Biological Activity for 8-pCPT-2-O-Me-cAMP-AM
8-pCPT-2-O-Me-cAMP-AM is a selective Epac activator; cAMP analog. Induces Rap activation and junction tightening in HUVECs; triggers adhesion of Jurkat-Epac1 cells to fibronectin. Stimulates insulin secretion in rat INS-1 cells. More potent, cell-permeable analog of 8CPT-2Me-cAMP (Cat. No. 1645).
This product is a mixture of axial and equatorial isomers. Both isomers give 8CPT-2Me-cAMP after esterase cleavage.
Licensing Information
Sold with the permission of BioLog Life Science Institute.
Technical Data for 8-pCPT-2-O-Me-cAMP-AM
| M. Wt | 557.9 |
| Formula | C20H21ClN5O8PS |
| Storage | Store at -20°C |
| Purity | ≥97% (HPLC) |
| CAS Number | 1152197-23-3 |
| PubChem ID | 90488978 |
| InChI Key | FZMWUFYPEVDWPA-SILPBKOMSA-N |
| Smiles | NC1=NC=NC2=C1N=C(SC4=CC=C(Cl)C=C4)N2[C@@H]3O[C@@](COP(O5)(OCOC(C)=O)=O)([H])[C@]5([H])[C@H]3OC |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for 8-pCPT-2-O-Me-cAMP-AM
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 55.79 | 100 |
Preparing Stock Solutions for 8-pCPT-2-O-Me-cAMP-AM
The following data is based on the product molecular weight 557.9. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.79 mL | 8.96 mL | 17.92 mL |
| 5 mM | 0.36 mL | 1.79 mL | 3.58 mL |
| 10 mM | 0.18 mL | 0.9 mL | 1.79 mL |
| 50 mM | 0.04 mL | 0.18 mL | 0.36 mL |
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Product Datasheets for 8-pCPT-2-O-Me-cAMP-AM
References for 8-pCPT-2-O-Me-cAMP-AM
References are publications that support the biological activity of the product.
Vliem et al (2008) 8-pCPT-2'-O-Me-cAMP-AM: an improved Epac-selective cAMP analogue. Chembiochem. 9 2052 PMID: 18633951
Almahariq et al (2013) A novel EPAC-specific inhibitor suppresses pancreatic cancer cell migration and invasion. Mol.Pharmacol. 83 122 PMID: 23066090
Tsalkova et al (2012) Isoform-specific antagonists of exchange proteins directly activated by cAMP. Proc.Natl.Acad.Sci.U.S.A. 109 18613 PMID: 23091014
Chepurny et al (2009) Enhanced Rap1 activation and Ins 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. J.Biol.Chem. 284 10728 PMID: 19244230
If you know of a relevant reference for 8-pCPT-2-O-Me-cAMP-AM, please let us know.
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Keywords: 8-pCPT-2-O-Me-cAMP-AM, 8-pCPT-2-O-Me-cAMP-AM supplier, 007-AM, cAMP, analogs, Epac, 1, 2, epacs, activators, cell, permeable, selective, Rap, guanine, nucleotide, exchange, factor, 3, 4, RAPGEF, GEFI, EPAC, 4853, Tocris Bioscience
10 Citations for 8-pCPT-2-O-Me-cAMP-AM
Citations are publications that use Tocris products. Selected citations for 8-pCPT-2-O-Me-cAMP-AM include:
Diana J et al (2019) Phospho-substrate profiling of Epac-dependent protein kinase C activity. Mol Cell Biochem 456 167-178 PMID: 30739223
Caglar et al (2019) Adenosine Receptor Signaling Targets Both PKA and Epac Pathways to Polarize Dendritic Cells to a Suppressive Phenotype. J Immunol 203 3247-3255 PMID: 31722989
Mishra et al (2018) Reactivation of cAMP Pathway by PDE4D Inhibition Represents a Novel Druggable Axis for Overcoming TAX Resistance in ER-positive Breast Cancer. Clin Cancer Res 24 1987 PMID: 29386221
Jason P et al (2020) Osmotic Gradients in Epithelial Acini Increase Mechanical Tension across E-cadherin, Drive Morphogenesis, and Maintain Homeostasis. Curr Biol 30 624-633.e4 PMID: 31983640
Mayati et al (2018) Functional polarization of human hepatoma HepaRG cells in response to forskolin. Sci Rep 8 1615 PMID: 30382126
Watson et al (2015) Endothelial CD99 signals through soluble adenylyl cyclase and PKA to regulate leukocyte transendothelial migration. Mol Brain 212 1021 PMID: 26101266
Derek C et al (2021) Regulation of Mitochondrial Function by Epac2 Contributes to Acute Inflammatory Hyperalgesia. J Neurosci 41 2883-2898 PMID: 33593853
Itender et al (2018) cAMP regulated EPAC1 supports microvascular density, angiogenic and metastatic properties in a model of triple negative breast cancer. Carcinogenesis 39 1245-1253 PMID: 29982410
Cheng-Mao et al (2018) The EPAC-Rap1 pathway prevents and reverses cytokine-induced retinal vascular permeability. J Biol Chem 293 717-730 PMID: 29158262
Fariba et al (2022) Respiratory syncytial virus disrupts the airway epithelial barrier by decreasing cortactin and destabilizing F-actin. J Cell Sci 135 PMID: 35848790
Do you know of a great paper that uses 8-pCPT-2-O-Me-cAMP-AM from Tocris? Please let us know.
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