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Merck

A165

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

≥98% (HPLC), cAMP antagonist, powder

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
UNSPSC Code:
41106305
PubChem Substance ID:
24890575
NACRES:
NA.77
MDL number:
MFCD03703495
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated

Key Documents

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Product Name

Rp-Adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt, powder, ≥98% (HPLC)

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

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 10 mg/mL

λmax

258 nm

storage temp.

−20°C

Quality Level

100

Related Categories

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.

Disclaimer

Extremely hygroscopic. Store desiccated.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000524809
0000524809
0000414859
0000309473
0000309473

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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)
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
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
Xiaohan Wang et al.
Hearing research, 377, 179-188 (2019-04-08)
Can damaged or degenerated vessels be regenerated in the ear? The question is clinically important, as disruption of cochlear blood flow is seen in a wide variety of hearing disorders, including in loud sound-induced hearing loss (endothelial injury), ageing-related hearing
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