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C5438

Sigma-Aldrich

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

≥95% (HPLC), powder

Sinônimo(s):

8-pCPT-cGMP, pCPT-cGMP

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About This Item

Fórmula empírica (Notação de Hill):
C16H14ClN5NaO7PS
Número CAS:
51239-26-0
Peso molecular:
509.79
Número MDL:
MFCD00674888
Código UNSPSC:
41106305
ID de substância PubChem:
24892786
NACRES:
NA.77

Ensaio

≥95% (HPLC)

forma

powder

cor

white

solubilidade

H2O: 25 mg/mL

temperatura de armazenamento

−20°C

cadeia de caracteres 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

chave InChI

REEQGIQRCDWDRA-ZBMQJGODSA-M

Categorias relacionadas

Aplicação

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).

Ações bioquímicas/fisiológicas

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.

Características e benefícios

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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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)
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)
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
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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Discover Bioactive Small Molecules for Cyclic Nucleotides

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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