93882-12-3

Basic information

• Product Name: 8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT
• Synonyms: 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
• CAS NO: 93882-12-3
• Molecular Formula: C16H14ClN5NaO6PS
• Molecular Weight: 493.79
• EINECS: 299-413-9
• Mol File: 93882-12-3.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 799.2 °C at 760 mmHg
• Flash Point: 437.1 °C
• Appearance: white/powder
• Storage Temp.: −20°C
• Solubility: H2O: 25 mg/mL
• CAS DataBase Reference: 8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: 8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT(93882-12-3)
• EPA Substance Registry System: 8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT(93882-12-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 93882-12-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 93882-12-3 differently. You can refer to the following data:
1. 8-CPT-cAMP is an efficient activator of cGK and cAMP-PK, and inhibitor of PDE.
2. 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 assayto 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).