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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
£47.70
50 MG
£138.00
100 MG
£255.00

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

£47.70

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000372931
0000340165
0000340217
0000337283
0000337288

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

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