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Sp-cAMPS sodium salt

Names

[ CAS No. ]:
142439-95-0

[ Name ]:
Sp-cAMPS sodium salt

[Synonym ]:
Sodium (2S,4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-7-hydroxytetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2-thiolate 2-oxide
4H-Furo[3,2-d]-1,3,2-dioxaphosphorin-7-ol, 6-(6-amino-9H-purin-9-yl)tetrahydro-2-mercapto-, 2-oxide, sodium salt, (2S,4aR,6R,7R,7aS)- (1:1)

Biological Activity

[Description]:

Sp-cAMPS sodium salt, a cAMP analog, is potent activator of cAMP-dependent PKA I 和 PKA II. Sp-cAMPS sodium salt is also a potent, competitive phosphodiesterase (PDE3A) inhibitor with a Ki of 47.6 µM. Sp-cAMPS sodium salt binds the PDE10 GAF domain with an EC50 of 40 μM[1][2][3].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE)
Signaling Pathways >> Protein Tyrosine Kinase/RTK >> PKA
Signaling Pathways >> Stem Cell/Wnt >> PKA
Research Areas >> Neurological Disease

[Target]

PKA I

PKA II

PDE3A:47.6 μM (Ki)

PDE10 GAF domain:50 μM (EC50)


[In Vitro]

Treatment of hepatocytes with Sp-cAMPS, the stimulatory diastereomer of adenosine cyclic 3',5'-phosphorothioate, mimics the response seen with glucagon. The glucagon-stimulated increases in the level of Ca2+ can be mimicked by Sp-cAMPS[4].

[In Vivo]

In chronic alcohol consumption (CAC) mice, direct infusion of the Sp-cAMPS (1 µg/µL) into the prefrontal cortex significantly improves or impairs, respectively, working memory performance in withdrawn and water animals[5].

[References]

[1]. Su H Hung, et al. A new nonhydrolyzable reactive cAMP analog, (Sp)-adenosine-3',5'-cyclic-S-(4-bromo-2,3-dioxobutyl)monophosphorothioate irreversibly inactivates human platelet cGMP-inhibited cAMP phosphodiesterase. Bioorg Chem. 2002 Feb;30(1):16-31.

[2]. L Y Wang, et al. Regulation of kainate receptors by cAMP-dependent protein kinase and phosphatases. Science. 1991 Sep 6;253(5024):1132-5.

[3]. Ronald Jäger, et al. Activation of PDE10 and PDE11 phosphodiesterases. J Biol Chem. 2012 Jan 6;287(2):1210-9.

[4]. P A Connelly,et al. A study of the mechanism of glucagon-induced protein phosphorylation in isolated rat hepatocytes using (Sp)-cAMPS and (Rp)-cAMPS, the stimulatory and inhibitory diastereomers of adenosine cyclic 3',5'-phosphorothioate. J Biol Chem. 1987 Mar 25;262(9):4324-32.

[5]. G Dominguez, et al. Rescuing prefrontal cAMP-CREB pathway reverses working memory deficits during withdrawal from prolonged alcohol exposure. Brain Struct Funct. 2016 Mar;221(2):865-77.

Chemical & Physical Properties

[ Molecular Formula ]:
C10H11N5NaO5PS

[ Molecular Weight ]:
367.253

[ Exact Mass ]:
367.011627

[ PSA ]:
182.50000

[ LogP ]:
0.96900

Related Compounds