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C3912

Sigma-Aldrich

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

≥97.0% (HPLC), powder

Todas las fotos(3)
Sinónimos:
pCPT-cAMP
Empirical Formula (Hill Notation):
C16H14ClN5NaO6PS
Número de CAS:
93882-12-3
Peso molecular:
493.79
Número de EC:
299-413-9
Número MDL:
MFCD00057683
ID de la sustancia en PubChem:
24278024
NACRES:
NA.77

Análisis

≥97.0% (HPLC)

formulario

powder

color

white

solubilidad

H2O: 25 mg/mL

temp. de almacenamiento

−20°C

SMILES string

[Na+].Nc1ncnc2n([C@@H]3O[C@@H]4COP([O-])(=O)O[C@H]4[C@H]3O)c(Sc5ccc(Cl)cc5)nc12

InChI

1S/C16H15ClN5O6PS.Na/c17-7-1-3-8(4-2-7)30-16-21-10-13(18)19-6-20-14(10)22(16)15-11(23)12-9(27-15)5-26-29(24,25)28-12;/h1-4,6,9,11-12,15,23H,5H2,(H,24,25)(H2,18,19,20);/q;+1/p-1/t9-,11-,12-,15-;/m1./s1

InChI key

YIJFVHMIFGLKQL-DNBRLMRSSA-M

Gene Information

human ... PRKAR1A(5573) , PRKAR1AP(5574) , PRKAR1B(5575) , PRKAR2A(5576) , PRKAR2B(5577)

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Este artículo
A2647A6885C5438
8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt ≥97.0% (HPLC), powder

Sigma-Aldrich

C3912

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

Adenosine 5′-(β,γ-imido)triphosphate lithium salt hydrate ≥93% (HPLC), powder

Sigma-Aldrich

A2647

Adenosine 5′-(β,γ-imido)triphosphate lithium salt hydrate

Adenosine 3′,5′-cyclic monophosphate sodium salt monohydrate ≥98.0% (HPLC), powder

Sigma-Aldrich

A6885

Adenosine 3′,5′-cyclic monophosphate sodium salt monohydrate

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

Sigma-Aldrich

C5438

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

form

powder

form

powder

form

powder

form

powder

color

white

color

white

color

white

color

white

solubility

H2O: 25 mg/mL

solubility

H2O: 50 mg/mL

solubility

H2O: 10 mg/mL

solubility

H2O: 25 mg/mL

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

Aplicación

8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt has been used:
  • to upregulate cellular cholesterol pump (adenosine triphosphate- (ATP-) binding cassette (ABC) transporter-1, ABCA-1)
  • in glucose production assay
  • to stimulate cystic fibrosis transmembrane conductance regulator (CFTR) channel in airway epithelia

Acciones bioquímicas o fisiológicas

Membrane permeable cAMP analog. Used as a selective activator of cAMP dependent protein kinase (PKA). Inhibits cGMP-dependent phosphodiesterase and, at higher concentrations, inhibits cAMP-dependent phosphodiesterase. Inhibits phosphoinositide hydrolysis and secretion stimulated by n-formyl-Met-Leu-Phe but not platelet-activating factor in leukocytes. Renders HL-60 cells more resistant to NO-induced DNA damage.

Características y beneficios

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.

Código de clase de almacenamiento

11 - Combustible Solids

WGK

WGK 3

Punto de inflamabilidad F

Not applicable

Punto de inflamabilidad C

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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T1503
Referencia del producto
-
25G
Tamaño del envase/cantidad

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introducir como1.000309185)

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

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ESI-09

J F Desaphy et al.
The American journal of physiology, 275(6 Pt 1), C1465-C1472 (1998-12-09)
Although the skeletal muscle sodium channel is a good substrate for cAMP-dependent protein kinase (PKA), no functional consequence was observed for this channel expressed in heterologous systems. Therefore, we investigated the effect of 8-(4-chlorophenylthio)adenosine 3',5'-cyclic monophosphate (CPT-cAMP), a membrane-permeable cAMP
Consumption of cuban policosanol improves blood pressure and lipid profile via enhancement of HDL functionality in healthy women subjects: randomized, double-blinded, and placebo-controlled study
Cho KH, et al.
Oxidative Medicine and Cellular Longevity, 2018 (2018)
In vitro Methods for the Development and Analysis of Human Primary Airway Epithelia
Gianotti A, et al.
Frontiers in Pharmacology, 9 (2018)
P Chavis et al.
Neuron, 20(4), 773-781 (1998-05-15)
Adenylyl cyclase (AC) modulation of vesicular cycling was visualized at cultured cerebellar granule cell synapses using the sequential uptake of antibodies directed against the intraluminal domain of synaptotagmin I. Vesicle recycling due to spontaneous transmitter release in the absence of
Aurora Maria Fontainhas et al.
Investigative ophthalmology & visual science, 52(1), 579-587 (2010-09-24)
An early injury response to retinal detachment is disruption of synaptic connectivity between photoreceptors and second-order neurons. Most dramatic is the retraction of rod cell axons and their terminals away from the outer synaptic layer and toward their cell bodies.
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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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