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93882-12-3

93882-12-3 Structure

93882-12-3 Structure
IdentificationBack Directory
[Name]

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

93882-12-3
[Synonyms]

pcpt-camp
8-CPT-CAMP, NA
8-PCPT-CAMP NA
CAMP, 8-PCPT-, NA
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
8-[(4-Chlorophenyl)thio]adenosine 3',5'-phosphoric acid sodium salt
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
ADENOSINE 3',5'-CYCLIC MONOPHOSPHATE, 8-(4-CHLOROPHENYLTHIO)-, SODIUM SALT
8-(4-Chlorophenylthio)adenosine 3',5'-(Cyclic)monophospphate Sodium Salt
8-(4-Chlorophenylthio)-adenosine-3'',5''-cyclic monophosphoric acid sodium sa
8-(4-chlorophenylthio)adenosine-3’,5’-cyclicmonophosphate(8-cpt-camp),sodiumsalt
8-(4-Chlorophenylthio)adenosine 3',5'-(Cyclic)monophosphate Sodium Salt, 98.0+ % (HPLC)
Adenosine, 8-[(4-chlorophenyl)thio]-, cyclic 3',5'-(hydrogen phosphate), monosodium salt
Adenosine 3,5-cyclic Monophosphate, 8-(4-Chlorophenylthio)-, Sodium Salt - CAS 93882-12-3 - Calbiochem
[EINECS(EC#)]

299-413-9
[Molecular Formula]

C16H14ClN5NaO6PS
[MDL Number]

MFCD00057683
[MOL File]

93882-12-3.mol
[Molecular Weight]

493.79
Chemical PropertiesBack Directory
[Melting point ]

227 - 232°C
[storage temp. ]

-20°C
[solubility ]

H2O: 25 mg/mL
[form ]

powder
[color ]

white
Safety DataBack Directory
[WGK Germany ]

3
Hazard InformationBack Directory
[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

[Uses]

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

Store at -20°C
[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).
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