C3912

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

Name: 8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt
Brand: SIGMA

≥97.0% (HPLC), cAMP analog, powder

Sinónimos:

pCPT-cAMP

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About This Item

Fórmula empírica (notación de Hill):

C₁₆H₁₄ClN₅NaO₆PS

Número CAS:

93882-12-3

Peso molecular:

493.79

NACRES:

NA.77

PubChem Substance ID:

24278024

UNSPSC Code:

41106305

EC Number:

299-413-9

MDL number:

MFCD00057683

Nombre del producto

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

InChI key

YIJFVHMIFGLKQL-DNBRLMRSSA-M

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

SMILES string

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

assay

≥97.0% (HPLC)

form

powder

color

white

solubility

H₂O: 25 mg/mL

storage temp.

−20°C

Quality Level

200

Gene Information

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

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Categorías relacionadas

Bioactive Small Molecules

Phosphates

Application

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

Biochem/physiol Actions

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.

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Visite la Librería de documentos

RhoA inactivation prevents photoreceptor axon retraction in an in vitro model of acute retinal detachment.

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.

Visualization of cyclic AMP-regulated presynaptic activity at cerebellar granule cells.

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

8-(4-Chlorophenyl)thio-cyclic AMP is a potent inhibitor of the cyclic GMP-specific phosphodiesterase (PDE VA).

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

Blockade by cAMP of native sodium channels of adult rat skeletal muscle fibers.

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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Product Information Sheet - C3912

Product Information Sheet

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