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Documenti fondamentali

A165

Sigma-Aldrich

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

powder, ≥98% (HPLC)

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C10H11N5O5PS · C6H16N
Numero CAS:
Peso molecolare:
446.46
Numero MDL:
Codice UNSPSC:
41106305
ID PubChem:
NACRES:
NA.77

Saggio

≥98% (HPLC)

Stato

powder

Condizioni di stoccaggio

desiccated

Colore

white to beige

Solubilità

H2O: 10 mg/mL

λmax

258 nm

Temperatura di conservazione

−20°C

Stringa SMILE

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
OXIPZMKSNMRTIV-NVGWRVNNSA-N

Categorie correlate

Applicazioni

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

Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

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.

Avvertenza

Extremely hygroscopic. Store desiccated.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


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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)

Contenuto correlato

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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