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A165

Sigma-Aldrich

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

powder, ≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C10H11N5O5PS · C6H16N
Numéro CAS:
151837-09-1
Poids moléculaire :
446.46
Numéro MDL:
MFCD03703495
Code UNSPSC :
41106305
ID de substance PubChem :
24890575
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Essai

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to beige

Solubilité

H2O: 10 mg/mL

λmax

258 nm

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Attention

Extremely hygroscopic. Store desiccated.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
116M4759V
033M4743V
032M4728V
010M47501
010M4750

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Shaomin Peng et al.
Investigative ophthalmology & visual science, 51(6), 3216-3225 (2010-01-01)
Bevacizumab and ranibizumab are currently used to treat age-related macular degeneration by neutralizing vascular endothelial growth factor (VEGF). In this study, the potential side effects on the outer blood-retinal barrier were examined. Human fetal RPE (hfRPE) cells were used because
J D Rothermel et al.
The Journal of biological chemistry, 259(13), 8151-8155 (1984-07-10)
The ability of the Rp diastereomer of adenosine cyclic 3',5'-phosphorothioate (Rp cAMPS) to inhibit glucagon-induced glycogenolysis was studied in hepatocytes isolated from fed rats. Preincubation of the cells for 20 min with progressively higher concentrations of Rp cAMPS followed by
L Y Wang et al.
Science (New York, N.Y.), 253(5024), 1132-1135 (1991-09-06)
In the mammalian central nervous system, receptors for excitatory amino acid neurotransmitters such as the alpha-amino-3-hydroxy-5-methyl-4- isoxazolepropionic acid (AMPA)-kainate receptor mediate a large fraction of excitatory transmission. Currents induced by activation of the AMPA-kainate receptor were potentiated by agents that
PKA-independent cAMP stimulation of white adipocyte exocytosis and adipokine secretion: modulations by Ca2+ and ATP
Komai AM, et al.
The Journal of Physiology, 592(23), 5169-5186 (2014)
cAMP analog antagonists of cAMP action.
L H Botelho et al.
Methods in enzymology, 159, 159-172 (1988-01-01)
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Contenu apparenté

Discover Bioactive Small Molecules for Cyclic Nucleotides

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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