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Adenosine-3’,5’-cyclic Monophosphothioate, Rp-Isomer . sodium salt

PKA inhibitor
 
ALX-480-085-M001 1 mg 182.00 USD
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Competitive inhibitor of cyclic AMP-dependent protein kinase I and II.
Metabolic stability towards mammalian cyclic nucleotide- responsive phosphodiesterases.
Discriminates between protein kinase A (antagonist) and some other cyclic AMP receptors, e.g. channels or CAP 3 (agonist).
Membrane-permeant for several systems (for improved permeability more lipophilic analogues e.g. Rp-8-Br-cAMPS (Prod. No. BML-CN216) are recommended).

Product Specification

Alternative Name:Rp-cAMPS . Na, cAMPS . Na, Rp-Isomer
 
Formula:C10H11N5O5PS . Na
 
MW:344.3 . 23.0
 
CAS:73208-40-9
 
Purity:≥99% (HPLC) (low adenosine, cAMP and Sp-cAMPS content)
 
Identity:Determined by MS and UV.
 
Appearance:White to off-white powder. Please keep in mind that equal amounts of the compound may look different in volume depending on humidity. Rp-cAMPS is hygroscopic and tends to form a transparent film on the bottom of the tube.
 
Solubility:Soluble in water or aqueous buffers, DMSO, Methanol.
 
Shipping:Ambient
 
Short Term Storage:Ambient
 
Long Term Storage:-20°C
 
Handling:Hygroscopic.
 
Scientific Background:Rp-cAMPS is an analogue of the natural signal molecule cyclic AMP in which the equatorial one of the two exocyclic oxygen atoms in the cyclic phosphate moiety is replaced by sulfur. The suffix "p" indicates that R/S nomenclature refers to phosphorus.
 
Technical Info/Product Notes:Since even minor impurities of cyclic AMP or the agonistic diastereomer Sp-cAMPS (0.2%) can already activate protein kinase A and compete with the antagonistic effect of the Rp- isomer, it is imperative to work with a strictly pure compound, especially concerning cyclic nucleotide contaminants. Cyclic AMP interference is not so important when working with cell cultures, since cAMP itself has very low membrane permeability and, in addition, would be metabolized immediately by both intracellular and external serum cyclic nucleotide-dependent phosphodiesterases.
Traces of the activator Sp-cAMPS, however, are fatal since it effectively competes with Rp-cAMPS and is only extremely slowly degraded by PDE. Another reason also demands for a pure reagent: Some cyclic AMP binding proteins other than kinases, such as some cyclic nucleotide-gated ion channels or the CAP protein, are activated by Rp-cAMPS. Thus, pure Rp-cAMPS can distinguish between protein kinase A and these receptors, but a contaminated reagent will yield misinformation.
This Rp-cAMPS is strictly checked for absence of activators such as Sp-cAMPS or cyclic AMP (< 0.05% when packed). Analysis of Rp-cAMPS from other sources, however, showed that this is not common practice.
 
ALX-480-085
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ALX-480-085

Product Literature References

Activation of Group II Metabotropic Glutamate Receptors Inhibits Glutamatergic Transmission in the Rat Entorhinal Cortex via Reduction of Glutamate Release Probability: S. Wang, et al.; Cereb. Cortex 22, 584 (2012), Abstract;
Delta Protocadherin 10 is Regulated by Activity in the Mouse Main Olfactory System: E.O. Williams, et al.; Front. Neural Circuits 5, (2011), Abstract; Full Text
Multidrug resistance protein 4 (MRP4/ABCC4) regulates cAMP cellular levels and controls human leukemia cell proliferation and differentiation: S. Copsel, et al.; J. Biol. Chem. 286, 6979 (2011), Abstract; Full Text
Acute stimulation of white adipocyte respiration by PKA-induced lipolysis: E. Yehuda-Shnaidman, et al.; Diabetes 59, 2474 (2010), Abstract; Full Text
Wnt-11 promotes neuroendocrine-like differentiation, survival and migration of prostate cancer cells: P. Uysal-Onganer, et al.; Mol. Cancer 9, 55 (2010), Abstract; Full Text
Antidepressant-like activity of 8-Br-cAMP, a PKA activator, in the forced swim test: P. Branski, et al.; J. Neural Transm. 115, 829 (2008), Abstract;
Epoxyeicosatrienoic acids regulate Trp channel dependent Ca2+ signaling and hyperpolarization in endothelial cells: I. Fleming, et al.; Arterioscler. Thromb. Vasc. Biol. 27, 2612 (2007), Abstract; Full Text
Cilostazol suppresses superoxide production and expression of adhesion molecules in human endothelial cells via mediation of cAMP-dependent protein kinase-mediated maxi-K channel activation: S.Y. Park, et al.; J. Pharmacol. Exp. Ther. 317, 1238 (2006), Abstract; Full Text
Effects of chronic portal hypertension on agonist-induced actin polymerization in small mesenteric arteries: X. Chen, et al.; Am. J. Physiol. Heart Circ. Physiol. 290, H1915 (2006), Abstract; Full Text

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