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C3912

Sigma-Aldrich

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

≥97.0% (HPLC), powder

Sinónimos:

pCPT-cAMP

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10 MG
MXP 1,924.00
50 MG
MXP 7,504.00
100 MG
MXP 12,052.00

MXP 1,924.00

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10 MG
MXP 1,924.00
50 MG
MXP 7,504.00
100 MG
MXP 12,052.00

About This Item

Fórmula empírica (notación de Hill):
C16H14ClN5NaO6PS
Número de CAS:
93882-12-3
Peso molecular:
493.79
Número CE:
299-413-9
Número MDL:
MFCD00057683
Código UNSPSC:
41106305
ID de la sustancia en PubChem:
24278024
NACRES:
NA.77

MXP 1,924.00

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Ensayo

≥97.0% (HPLC)

Formulario

powder

color

white

solubilidad

H2O: 25 mg/mL

temp. de almacenamiento

−20°C

cadena SMILES

[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

Clave InChI

YIJFVHMIFGLKQL-DNBRLMRSSA-M

Información sobre el gen

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

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Categorías relacionadas

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)[1]
  • in glucose production assay[2]
  • to stimulate cystic fibrosis transmembrane conductance regulator (CFTR) channel in airway epithelia[3]

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000436362
0000436360
0000436360
0000436362
0000372931

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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.
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
Olivia J S Macleod et al.
Nature communications, 11(1), 1326-1326 (2020-03-14)
Persistent pathogens have evolved to avoid elimination by the mammalian immune system including mechanisms to evade complement. Infections with African trypanosomes can persist for years and cause human and animal disease throughout sub-Saharan Africa. It is not known how trypanosomes
Madhu Nath et al.
Frontiers in neuroscience, 16, 912757-912757 (2022-06-08)
Phosphatidylinositol 3-kinase (PI3K)/Akt signal pathway mediates pro-survival function in neurons. In the retina, PI3K/AKT/mTOR signaling pathway is related to the early pathogenesis of diabetic retinopathy. Signaling molecules in the membrane-initiated signaling pathway exhibiting neuroprotective function interacts with the PI3K/Akt pathway
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
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Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

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