151837-09-1

151837-09-1 structure

Name: cAMPS-Rp, triethylammonium salt
Chemical Name: Rp-Adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt hydrate
CAS Number: 151837-09-1
Molecular Formula: C₁₆H₂₇N₆O₅PS
Molecular Weight: 446.46200
Catalog: Signaling Pathways Protein Tyrosine Kinase/RTK PKA
Create Date: 2016-01-18 08:27:02
Modify Date: 2024-01-03 08:23:24
Rp-cAMPS triethylammonium salt is an analog of cAMP which acts as a potent, competitive and cell-permeable antagonist of cAMP-induced activation of cAMP-dependent PKA I and II (Kis of 6.05 µM and 9.75 µM, respectively). Rp-cAMPS triethylammonium salt is resistant to hydrolysis by phosphodiesterases[1][2][3][4][5].

Name	Rp-Adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt hydrate
Synonyms	MFCD03703495 cAMPS-Rp,triethylammonium salt

Description	Rp-cAMPS triethylammonium salt is an analog of cAMP which acts as a potent, competitive and cell-permeable antagonist of cAMP-induced activation of cAMP-dependent PKA I and II (Kis of 6.05 µM and 9.75 µM, respectively). Rp-cAMPS triethylammonium salt is resistant to hydrolysis by phosphodiesterases[1][2][3][4][5].
Related Catalog	Signaling Pathways >> Protein Tyrosine Kinase/RTK >> PKA Signaling Pathways >> Stem Cell/Wnt >> PKA Research Areas >> Neurological Disease
Target	Ki: 6.05 µM (PKA I) and 9.75 µM (PKA II)[1]
In Vitro	A membrane-permeable competitive cAMP antagonist (Rp-cAMPS) that blocks PKA activation by binding to the regulatory subunits without dissociating the kinase holoenzyme also inhibits synaptic plasticity but has no effect on normal synaptic transmission[1].
In Vivo	Rp-cAMPS (10 μM, 15 min) decreases the monosynaptic EPSCs evoked at the PB-CeLC and BLA-CeLC synapses in slices from arthritic rats but not in control neurons from normal animals. The inhibitory effect of Rp-cAMPS is significant compared to predrug (ACSF) control values obtained in the same neurons[1].
References	[1]. Rothermel JD, et al. A mechanistic and kinetic analysis of the interactions of the diastereoisomers of adenosine 3',5'-(cyclic)phosphorothioate with purified cyclic AMP-dependent protein kinase. Biochem J. 1988 May 1;251(3):757-62. [2]. Fu Y, et al. PKA and ERK, but not PKC, in the amygdala contribute to pain-related synaptic plasticity and behavior. Mol Pain. 2008 Jul 16;4:26. [3]. Kuriyama S, et al. Isoproterenol inhibits rod outer segment phagocytosis by both cAMP-dependent and independent pathways. Invest Ophthalmol Vis Sci. 1995 Mar;36(3):730-6. [4]. Dostmann WR, et al. Probing the cyclic nucleotide binding sites of cAMP-dependent protein kinases I and II with analogs of adenosine 3',5'-cyclic phosphorothioates. J Biol Chem. 1990 Jun 25;265(18):10484-91. [5]. Van Haastert PJ, et al. Competitive cAMP antagonists for cAMP-receptor proteins. J Biol Chem. 1984 Aug 25;259(16):10020-4.

Melting Point	212 - 213 ℃
Molecular Formula	C₁₆H₂₇N₆O₅PS
Molecular Weight	446.46200
Exact Mass	446.15000
PSA	186.46000
LogP	2.04940

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