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C3912

Sigma-Aldrich

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

≥97.0% (HPLC), powder

Synonym(s):

pCPT-cAMP

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10 MG
$85.32
50 MG
$276.00
100 MG
$472.00

About This Item

Empirical Formula (Hill Notation):
C16H14ClN5NaO6PS
CAS Number:
93882-12-3
Molecular Weight:
493.79
EC Number:
299-413-9
MDL number:
MFCD00057683
UNSPSC Code:
41106305
PubChem Substance ID:
24278024
NACRES:
NA.77

$85.32

List Price$94.80Save 10%

In StockDetails

Request a Bulk Order

Quality Level

200

assay

≥97.0% (HPLC)

form

powder

color

white

solubility

H2O: 25 mg/mL

storage temp.

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

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000372931
0000337288
0000337283
0000372931
0000340217

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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)
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
In vitro Methods for the Development and Analysis of Human Primary Airway Epithelia
Gianotti A, et al.
Frontiers in Pharmacology, 9 (2018)
H Ali et al.
The Journal of biological chemistry, 273(18), 11012-11016 (1998-06-06)
Formylated peptides (e.g. n-formyl-Met-Leu-Phe (fMLP)) and platelet-activating factor (PAF) mediate chemotactic and cytotoxic responses in leukocytes through receptors coupled to G proteins that activate phospholipase C (PLC). In RBL-2H3 cells, fMLP utilizes a pertussis toxin (ptx)-sensitive G protein to activate
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
View All Related Papers

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Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

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