ChemicalBook > CAS DataBase List > 8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT

8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT

Product Name
8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT
CAS No.
93882-12-3
Chemical Name
8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT
Synonyms
pcpt-camp;8-CPT-CAMP, NA;8-PCPT-CAMP NA;CAMP, 8-PCPT-, NA;8-CPT-cAMP sodium;8-(p-Chlorophenylthio;8-CPT-CAMP SODIUM SALT;8-CPT-Cyclic AMP (sodium salt);8-(4-CHLOROPHENYLTHIO)-CAMP SODIUM;8-(4-CHLOROPHENYLTHIO)ADENOSINE 3':5'-CY CLIC MONOP
CBNumber
CB1676640
Molecular Formula
C16H14ClN5NaO6PS
Formula Weight
493.79
MOL File
93882-12-3.mol
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8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT Property

Melting point:
227 - 232°C
storage temp. 
-20°C
solubility 
H2O: 25 mg/mL
form 
powder
color 
white
Water Solubility 
water: 10mg/mL
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C3912
Product name
8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt
Purity
≥97.0% (HPLC), powder
Packaging
10mg
Price
$92.2
Updated
2024/03/01
Sigma-Aldrich
Product number
116812
Product name
Adenosine 3?,5?-cyclic Monophosphate, 8-(4-Chlorophenylthio)-, Sodium Salt
Packaging
10mg
Price
$82.8
Updated
2024/03/01
Cayman Chemical
Product number
12011
Product name
8-CPT-Cyclic AMP (sodium salt)
Purity
≥98%
Packaging
10mg
Price
$57
Updated
2024/03/01
Cayman Chemical
Product number
12011
Product name
8-CPT-Cyclic AMP (sodium salt)
Purity
≥98%
Packaging
25mg
Price
$105
Updated
2024/03/01
Sigma-Aldrich
Product number
C3912
Product name
8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt
Purity
≥97.0% (HPLC), powder
Packaging
50mg
Price
$268
Updated
2024/03/01
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8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT Chemical Properties,Usage,Production

Uses

8-CPT-cAMP is an efficient activator of cGK and cAMP-PK, and inhibitor of PDE.

Uses

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

General Description

Cell-permeable cAMP analog that activates both protein kinase A and protein kinase G. Directly activates Epac, a Rap1 guanine-nucleotide exchange factor. Also acts as a potent inhibitor of cGMP-specific phosphodiesterase (IC50 = 900 nM). Inhibits cAMP-specific phosphodiesterase at much higher concentrations (IC50 = 25 μM).

Biological Activity

ka : 0.05 and 0.11 μm for pka and pkg, respectively8-cpt-cyclic amp is a lipophilic activator of the cyclic-amp- and cyclic-gmp-dependent protein kinases, pka and pkg.the ability of cgmp-dependent protein kinases (cgks) to activate camp response element (cre)-dependent gene transcription was compared with that of camp-dependent protein kinases (caks).

Biochem/physiol Actions

Cell permeable: yes

in vitro

a previous study found that 8-cpt-cyclic amp was a potent activator of camp-pk and cyclic-gmp-dependent protein kinase (cgmp-pk) both as purified enzymes and in platelet membranes. 8-cpt-cyclic amp was hydrolysed to a significant extent by the ca2+/calmodulin-dependent phosphodiesterase and by the cgmp-inhibited phosphodiesterase. moreover, sp-5,6- dcl-cbimps was also more effective than 8-cpt-cyclic amp in inducing quantitative phosphorylation of vasodilator-stimulated phosphoprotein in intact platelets [1]. another study indicated that 8-cpt-cyclic amp was a potent inhibitor of the cyclic gmp-specific phosphodiesterase (pde va). indeed, 8-cpt-cyclic amp could inhibit pde va with a potency similar to that of zaprinast. in addition, 8-cpt-cyclic amp was metabolized by pde va at a rate half that of cyclic gmp. the cyclic gmp-inhibited phosphodiesterase and the cyclic amp-specific phosphodiesterase could be inhibited by 8-cpt-cyclic amp as well [2].

References

[1] sandberg, m. ,butt, e.,nolte, c., et al. characterization of sp-5,6-dichloro-1-β-d-ribofuranosylbenzimidazole-3',5'-monophosphorothioate (sp-5,6-dcl-cbimps) as a potent and specific activator of cyclic-amp-dependent protein kinase in cell extracts and intact cells. biochemistry journal 279, 521-527 (1991).
[2] connolly, b. j.,willits, p.b.,warrington, b.h., et al. 8-(4-chlorophenyl)thio-cyclic amp is a potent inhibitor of the cyclic gmp-specific phosphodiesterase (pde va). biochemical pharmacology 44(12), 2303-2306 (1992).

8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT Preparation Products And Raw materials

Raw materials

Preparation Products

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8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT Suppliers

China 27 Germany 2 Japan 1 Switzerland 2 United Kingdom 4 United States 14 Global 50
3B Pharmachem (Wuhan) International Co.,Ltd.
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93882-12-3, 8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALTRelated Search:

8-CHLORO-CAMP PROTEIN KINASE A INHIBITOR 14-22 AMIDE, CELL-PERMEABLE, MYRISTOYLATED 8-Mercaptopurine 2-MERCAPTOIMIDAZOLE Adenine hydrochloride Adenine hydrochloride hemihydrate 6-amino-1,7-dihydro-8H-purine-8-thione Adenine Sulfate Adenosine Cyclic AMP Adenosine 3',5'-cyclic monophosphate sodium salt 8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT 2'-DCAMP SODIUM SALT 8-MERCAPTOADENOSINE Adenosinehydrochloride (S)-3-AMINO-1,2-DIHYDROXYPROPANE HYDROCHLORIDE 8-(4-CHLOROPHENYLTHIO)-2',O-METHYLADENOSINE 3',5'-CYCLIC MONOPHOSPHATE SODIUM SALT CPUMP SODIUM SALT

  • CAMP, 8-PCPT-, NA
  • ADENOSINE 3',5'-CYCLIC MONOPHOSPHATE, 8-(4-CHLOROPHENYLTHIO)-, SODIUM SALT
  • 8-CPT-CAMP, NA
  • 8-CPT-CAMP SODIUM SALT
  • 8-PCPT-CAMP NA
  • 8-(4-CHLOROPHENYLTHIO) ADENOSINE-3',5'-CYCLIC MONOPHOSPHATE SODIUM SALT
  • 8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT
  • 8-[(4-CHLOROPHENYL)THIO]-ADENOSINE CYCLIC 3',5'-HYDROGEN PHOSPHATE SODIUM
  • 8-(4-CHLOROPHENYLTHIO)-CAMP SODIUM
  • 8-(4-chlorophenylthio)adenosine-3’,5’-cyclicmonophosphate(8-cpt-camp),sodiumsalt
  • Adenosine, 8-[(4-chlorophenyl)thio]-, cyclic 3',5'-(hydrogen phosphate), monosodium salt
  • 8-(4-CHLOROPHENYLTHIO)ADENOSINE 3':5'-CY CLIC MONOP
  • pcpt-camp
  • Adenosine 3,5-cyclic Monophosphate, 8-(4-Chlorophenylthio)-, Sodium Salt - CAS 93882-12-3 - Calbiochem
  • 8-(4-Chlorophenylthio)-adenosine-3'',5''-cyclic monophosphoric acid sodium sa
  • 8-[(4-Chlorophenyl)thio]adenosine 3',5'-phosphoric acid sodium salt
  • 8-(4-Chlorophenylthio)adenosine 3',5'-(Cyclic)monophospphate Sodium Salt
  • 8-CPT-Cyclic AMP (sodium salt)
  • 8-(4-Chlorophenylthio)adenosine 3',5'-(Cyclic)monophosphate Sodium Salt, 98.0+ % (HPLC)
  • 8-(p-Chlorophenylthio
  • 8-CPT-cAMP sodium
  • Sodium (4aR,6R,7R,7aS)-6-(6-amino-8-((4-chlorophenyl)thio)-9H-purin-9-yl)-7-hydroxytetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-olate 2-oxide
  • 8-(4-Chlorophenylthio)adenosine 3',5'-cyclic monophosphate
  • 8-(4-Chlorophenylthio)adenosine 3'',5''-cyclic monophosphate (8-CPT-cAMP), Cell permeable cAMP analog.
  • 93882-12-3
  • C16H15ClN5O6PS
  • C16H14ClN5O6PSNa
  • C16H14ClN5NaO6PS
  • Cell Signaling and Neuroscience
  • Cell Biology
  • BioChemical
  • G Proteins and Cyclic Nucleotides
  • Cyclic Nucleotides and Analogs
  • Cyclic Nucleotide Metabolism