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C3912

Sigma-Aldrich

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

≥97.0% (HPLC), powder

Sinônimo(s):

pCPT-cAMP

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About This Item

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

Ensaio

≥97.0% (HPLC)

Formulário

powder

cor

white

solubilidade

H2O: 25 mg/mL

temperatura de armazenamento

−20°C

cadeia de caracteres 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

chave InChI

YIJFVHMIFGLKQL-DNBRLMRSSA-M

Informações sobre genes

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

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Categorias relacionadas

Aplicação

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

Ações bioquímicas/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 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.

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

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
0000436362
0000436360
0000436360
0000436362
0000372931

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Slide 1 of 2

1 of 2

cAMP cAMP used to activate PKA in vitro.

Sigma-Aldrich

20-198

cAMP

ESI-09 ≥98% (HPLC)

Sigma-Aldrich

SML0814

ESI-09

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
B J Connolly et al.
Biochemical pharmacology, 44(12), 2303-2306 (1992-12-15)
8-(4-Chlorophenyl)thio-cyclic AMP (8-CPT-cAMP), extensively used as selective activator of cyclic AMP-dependent protein kinase, has been found to be a potent inhibitor of the cyclic GMP-specific phosphodiesterase (PDE VA). Indeed, 8-CPT-cAMP (IC50 = 0.9 microM) inhibited PDE VA with a potency
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)
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Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

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