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C5438

Sigma-Aldrich

8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphate sodium salt

≥95% (HPLC), powder

Synonyme(s) :

8-pCPT-cGMP, pCPT-cGMP

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About This Item

Formule empirique (notation de Hill):
C16H14ClN5NaO7PS
Numéro CAS:
51239-26-0
Poids moléculaire :
509.79
Numéro MDL:
MFCD00674888
Code UNSPSC :
41106305
ID de substance PubChem :
24892786
Nomenclature NACRES :
NA.77
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Niveau de qualité

200

Essai

≥95% (HPLC)

Forme

powder

Couleur

white

Solubilité

H2O: 25 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

[Na+].NC1=Nc2c(nc(Sc3ccc(Cl)cc3)n2[C@@H]4O[C@@H]5COP([O-])(=O)O[C@H]5[C@H]4O)C(=O)N1

InChI

1S/C16H15ClN5O7PS.Na/c17-6-1-3-7(4-2-6)31-16-19-9-12(20-15(18)21-13(9)24)22(16)14-10(23)11-8(28-14)5-27-30(25,26)29-11;/h1-4,8,10-11,14,23H,5H2,(H,25,26)(H3,18,20,21,24);/q;+1/p-1/t8-,10-,11-,14-;/m1./s1

Clé InChI

REEQGIQRCDWDRA-ZBMQJGODSA-M

Catégories apparentées

Application

8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphate sodium salt has been used to activate GMP-dependent protein kinase (PKG) in vascular smooth muscle cells (VSMCs).[1]

Actions biochimiques/physiologiques

Membrane-permeable analog of cGMP that does not affect cGMP-regulated phosphodiesterase. A more potent cGMP analog than 8-Br-cGMP due to greater membrane permeability and a higher resistance to hydrolysis by phosphodiesterase. Used as a selective activator of cGMP dependent protein kinase (PKG). Found to be a very potent cyclic nucleotide-gated channel agonist.

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.
This compound is featured on the PKA & PKG page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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

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Certificats d'analyse (COA)

Lot/Batch Number
0000353336
0000353336
SLCC7040
SLBX5098
SLBM7571V

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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

P He et al.
The American journal of physiology, 274(6 Pt 2), H1865-H1874 (1998-06-25)
To investigate the mechanisms whereby guanosine 3',5'-cyclic monophosphate (cGMP) modulates microvessel permeability in vivo, we measured changes in microvessel hydraulic conductivity (Lp) and endothelial cytoplasmic Ca2+ concentration ([Ca2+]i) in response to the cGMP analogs 8-bromo-cGMP (8-BrcGMP) and 8-(p-chlorophenylthio)cGMP (8-pCPT-cGMP) in
M Suhasini et al.
Molecular and cellular biology, 18(12), 6983-6994 (1998-11-20)
Agents which increase the intracellular cyclic GMP (cGMP) concentration and cGMP analogs inhibit cell growth in several different cell types, but it is not known which of the intracellular target proteins of cGMP is (are) responsible for the growth-suppressive effects
Yang Chen et al.
Circulation research, 124(10), 1462-1472 (2019-04-02)
Acute kidney injury (AKI) has a high prevalence and mortality in critically ill patients. It is also a powerful risk factor for heart failure incidence driven by hemodynamic changes and neurohormonal activation. However, no drugs have been approved by the
Richard B Thorpe et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 304(9), R734-R743 (2013-03-01)
Chronic hypoxia attenuates soluble guanylate cyclase-induced vasorelaxation in serotonin (5-HT)-contracted ovine carotid arteries. Because protein kinase G (PKG) mediates many effects of soluble guanylate cyclase activation through phosphorylation of multiple kinase targets in vascular smooth muscle, we tested the hypothesis
B E VanUffelen et al.
Biochemical pharmacology, 56(8), 1061-1063 (1998-10-17)
In previous experiments, it was shown that migration of electropermeabilized human neutrophils induced by a combination of cGMP and cAMP markedly lower relative to that induced by cGMP or cAMP alone. However, when cGMP was replaced with 8-(para-chlorophenylthio-guanosine-3',5'-cyclic monophosphate (8-pCPT-cGMP)
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