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Merck

C5438

Sigma-Aldrich

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

≥95% (HPLC), powder

Sinónimos:

8-pCPT-cGMP, pCPT-cGMP

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About This Item

Fórmula empírica (notación de Hill):
C16H14ClN5NaO7PS
Número de CAS:
Peso molecular:
509.79
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Categorías relacionadas

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Journal of Vascular Research, 47(4), 309-322 (2010)
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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
J Y Wei et al.
Journal of molecular neuroscience : MN, 10(1), 53-64 (1998-05-20)
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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

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