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A165

Sigma-Aldrich

Rp-Adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt

powder, ≥98% (HPLC)

Synonym(s):

Rp-Cyclic 3′,5′-hydrogen phosphorothioate adenosine triethylammonium salt, Rp-cAMPS triethylammonium salt

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About This Item

Empirical Formula (Hill Notation):
C10H11N5O5PS · C6H16N
CAS Number:
151837-09-1
Molecular Weight:
446.46
MDL number:
MFCD03703495
UNSPSC Code:
41106305
PubChem Substance ID:
24890575
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 10 mg/mL

λmax

258 nm

storage temp.

−20°C

SMILES string

CCN(CC)CC.Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4COP(O)(=S)O[C@H]4[C@H]3O

InChI

1S/C10H12N5O5PS.C6H15N/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(19-10)1-18-21(17,22)20-7;1-4-7(5-2)6-3/h2-4,6-7,10,16H,1H2,(H,17,22)(H2,11,12,13);4-6H2,1-3H3/t4-,6-,7-,10-,21?;/m1./s1

InChI key

OXIPZMKSNMRTIV-NVGWRVNNSA-N

Application

Rp-Adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt has been used as an antagonist of cAMP to block the cAMP-PKA signal pathway.

Biochem/physiol Actions

Rp-Adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt is capable of inhibiting protein kinase A (PKA).
Rp-Diastereomer of adenosine-3′,5′-cyclic monophosphothioate. Specific membrane-permeable inhibitor of activation by cAMP of cAMP-dependent protein kinase I and II; resistant toward cyclic nucleotide phosphodiesterases; blocks cAMP-mediated effects in numerous systems.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Caution

Extremely hygroscopic. Store desiccated.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Takashi Matsuura et al.
Journal of oral science, 60(4), 634-637 (2018-06-01)
Once a tooth develops deep caries and the dental pulp tissue is irreversibly infected, the infected dental pulp tissue should be removed, and filling material should be placed in the root canal. Endodontically treated teeth are prone to root fracture
Role of PLC-PIP2 and cAMP-PKA signal pathways in radiation-induced immune-suppressing effect
Dong JC, et al.
Biomedical and Environmental Sciences : Bes, 27(1), 27-34 (2014)
Carmen Müllner et al.
The FEBS journal, 276(21), 6218-6226 (2009-09-22)
Besides being activated by G-protein beta/gamma subunits, G-protein activated potassium channels (GIRKs) are regulated by cAMP-dependent protein kinase. Back-phosphorylation experiments have revealed that the GIRK1 subunit is phosphorylated in vivo upon protein kinase A activation in Xenopus oocytes, whereas phosphorylation
cAMP analog antagonists of cAMP action.
L H Botelho et al.
Methods in enzymology, 159, 159-172 (1988-01-01)
Olav A Gressner et al.
Liver international : official journal of the International Association for the Study of the Liver, 29(6), 886-897 (2009-03-18)
Recently, we identified hepatocytes as the major cellular source of profibrogenic connective tissue growth factor (CTGF/CCN2) in the liver. Based on reports of a hepatoprotective effect of coffee consumption, we were the first to provide evidence that caffeine suppresses transforming
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