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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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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

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)
  • 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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
In vitro Methods for the Development and Analysis of Human Primary Airway Epithelia
Gianotti A, et al.
Frontiers in Pharmacology, 9 (2018)
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
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
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
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