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8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic Monophosphate sodium salt (CAS 510774-50-2) - chemical structure ima
Molecular structure of 8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic Monophosphate sodium salt, CAS Number: 510774-50-2
8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic Monophosphate sodium salt (CAS 510774-50-2) - chemical structure ima
Molecular structure of 8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic Monophosphate sodium salt, CAS Number: 510774-50-2
Molecular structure of 8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic Monophosphate sodium salt, CAS Number: 510774-50-2

8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic Monophosphate sodium salt (CAS 510774-50-2)

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Alternate Names:
8-CPT-2′-O-Me-cAMP Na
Application:
8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic Monophosphate sodium salt is an activator of the Epac cAMP receptor
CAS Number:
510774-50-2
Purity:
≥98%
Molecular Weight:
507.82
Molecular Formula:
C17H16ClN5O6PS•Na
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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SDS & Certificate of Analysis

8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic Monophosphate sodium salt is a specific, potent and membrane permeant activator of the Epac cAMP receptor. The compound activates Epac1 and Epac2, the guanine nucleotide-exchange factors (GEFs) for the small GTPases Rap1 and Rap2. 8-CPT-2′-O-Me-cAMP. Na Does not activate protein kinase A (PKA), and is therefore useful to specifically discriminate between PKA- and Epac-mediated effects. Since a free 2′-ribose hydroxyl group in cyclic AMP is essential for stimulation of PKA, the methylated structure of 8-CPT-2′-O-Me-cAMP. Na is an extremely poor PKA activator. 8-CPT-2′-O-Me-cAMP. Na has a high lipophilicity which allows for good membrane permeability in most biosystems and its increased resistance towards phosphodiesterases prevents rapid hydrolysis.


8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic Monophosphate sodium salt (CAS 510774-50-2) References

  1. A novel Epac-specific cAMP analogue demonstrates independent regulation of Rap1 and ERK.  |  Enserink, JM., et al. 2002. Nat Cell Biol. 4: 901-6. PMID: 12402047
  2. Epac-selective cAMP analog 8-pCPT-2'-O-Me-cAMP as a stimulus for Ca2+-induced Ca2+ release and exocytosis in pancreatic beta-cells.  |  Kang, G., et al. 2003. J Biol Chem. 278: 8279-85. PMID: 12496249
  3. Cyclic AMP induces integrin-mediated cell adhesion through Epac and Rap1 upon stimulation of the beta 2-adrenergic receptor.  |  Rangarajan, S., et al. 2003. J Cell Biol. 160: 487-93. PMID: 12578910
  4. Cyclic AMP potentiates vascular endothelial cadherin-mediated cell-cell contact to enhance endothelial barrier function through an Epac-Rap1 signaling pathway.  |  Fukuhara, S., et al. 2005. Mol Cell Biol. 25: 136-46. PMID: 15601837
  5. Lysophosphatidic acid and endothelin-induced proliferation of ovarian cancer cell lines is mitigated by neutralization of granulin-epithelin precursor (GEP), a prosurvival factor for ovarian cancer.  |  Kamrava, M., et al. 2005. Oncogene. 24: 7084-93. PMID: 16044162
  6. Activators of Epac proteins induce relaxation of isolated rat aorta.  |  Sukhanova, IF., et al. 2006. Dokl Biol Sci. 411: 441-4. PMID: 17425034
  7. Interaction between TCL1 and Epac1 in the activation of Akt kinases in plasma membranes and nuclei of 8-CPT-2-O-Me-cAMP-stimulated macrophages.  |  Misra, UK., et al. 2008. Cell Signal. 20: 130-8. PMID: 17993260
  8. The cAMP-activated GTP exchange factor, Epac1 upregulates plasma membrane and nuclear Akt kinase activities in 8-CPT-2-O-Me-cAMP-stimulated macrophages: Gene silencing of the cAMP-activated GTP exchange Epac1 prevents 8-CPT-2-O-Me-cAMP activation of Akt activity in macrophages.  |  Misra, UK., et al. 2008. Cell Signal. 20: 1459-70. PMID: 18495429
  9. PKA-dependent and independent cAMP signaling in 3T3-L1 fibroblasts differentiation.  |  Martini, CN., et al. 2009. Mol Cell Endocrinol. 298: 42-7. PMID: 19010385
  10. Novel adenosine and cAMP signalling pathways in migrating glial cells.  |  Bernascone, S., et al. 2010. Cell Calcium. 48: 83-90. PMID: 20688392
  11. PKA and Epac synergistically inhibit smooth muscle cell proliferation.  |  Hewer, RC., et al. 2011. J Mol Cell Cardiol. 50: 87-98. PMID: 20971121
  12. Adiponectin attenuates angiotensin II-induced oxidative stress in renal tubular cells through AMPK and cAMP-Epac signal transduction pathways.  |  Fang, F., et al. 2013. Am J Physiol Renal Physiol. 304: F1366-74. PMID: 23535586
  13. The cAMP effector EPAC activates Elk1 transcription factor in prostate smooth muscle, and is a minor regulator of α1-adrenergic contraction.  |  Hennenberg, M., et al. 2013. J Biomed Sci. 20: 46. PMID: 23815815

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic Monophosphate sodium salt, 1 mg

sc-202028
1 mg
$311.00

8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic Monophosphate sodium salt, 5 mg

sc-202028A
5 mg
$974.00

What is the solubility of sc-202028 in DMSO?

Asked by: SCchem16
Thank you for your question. The compound, sc-202028, is soluble in water, aqueous buffers, DMSO, dimethyl formamide, and methanol. Unfortunately, we do not have the working concentrations. If you have any further questions or concerns, please feel free to contact our Technical Service department by calling 800-457-3801 option 2, emailing scbt@scbt.com, or using the Live Chat function on our website.
Answered by: Tech Service 8
Date published: 2017-01-31
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Rated 5 out of 5 by from BrynBryn, T. et al. (PubMed 16751380) used the Epac cAMP receptor activator, 8-(4-Chlorophenylthio)-2'-O-methyladenosine 3',5'-cyclic Monophosphate sodium salt, to demonstrate that the cyclic AMP-Epac1-Rap1 pathway is dissociated from regulation of effector functions in monocytes but acquires immunoregulatory function in mature macrophages. -SCBT Publication Review
Date published: 2015-01-23
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8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic Monophosphate sodium salt is rated 5.0 out of 5 by 1.
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