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C5438

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

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

Synonym(s):

8-pCPT-cGMP, pCPT-cGMP

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About This Item

Empirical Formula (Hill Notation):
C16H14ClN5NaO7PS
CAS Number:
51239-26-0
Molecular Weight:
509.79
UNSPSC Code:
41106305
PubChem Substance ID:
24892786
NACRES:
NA.77
MDL number:
MFCD00674888
Assay:
≥95% (HPLC)
Form:
powder
Quality level:
200
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Product Name

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

Quality Level

200

assay

≥95% (HPLC)

form

powder

color

white

solubility

H2O: 25 mg/mL

storage temp.

−20°C

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

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 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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000558028
0000558028
0000512518
0000512518
0000462973

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Articles

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

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
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
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Global Trade Item Number

SKUGTIN
C5438-10MG04061833502136
C5438-50MG04061832897714