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Merck

C5438

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

≥95% (HPLC), cGMP dependent protein kinase (PKG) activator, powder

Synonyme(s) :

8-pCPT-cGMP, pCPT-cGMP

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A propos de cet article

Formule empirique (notation de Hill) :
C16H14ClN5NaO7PS
Numéro CAS:
51239-26-0
Poids moléculaire :
509.79
UNSPSC Code:
41106305
PubChem Substance ID:
24892786
NACRES:
NA.77
MDL number:
MFCD00674888

Principaux documents

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Nom du produit

8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphate sodium salt, ≥95% (HPLC), powder

SMILES string

[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

InChI key

REEQGIQRCDWDRA-ZBMQJGODSA-M

assay

≥95% (HPLC)

form

powder

color

white

solubility

H2O: 25 mg/mL

storage temp.

−20°C

Quality Level

200

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).

Biochem/physiol Actions

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.

Features and Benefits

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.
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.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000512518
0000512518
0000462973
0000462973
0000353336

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Consulter la Bibliothèque de documents

J Y Wei et al.
Journal of molecular neuroscience : MN, 10(1), 53-64 (1998-05-20)
Cyclic nucleotide-gated (CNG) channels are expressed in many cell types in both the nervous system and nonexcitable tissues. In order to understand the roles of cGMP-gated channels, and to distinguish actions of cGMP mediated through CNG channels from those through
Stainless steel ions stimulate increased thrombospondin-1-dependent TGF-beta activation by vascular smooth muscle cells: implications for in-stent restenosis
Pallero MA, et al.
Journal of Vascular Research, 47(4), 309-322 (2010)
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)
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
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