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

Melting point:

227 - 232°C

storage temp. 

-20°C

solubility 

H₂O: 25 mg/mL

form 

powder

color 

white

Safety Information

WGK Germany 

3

MSDS

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

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(93882-12-3)Related Product Information

• 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