C3912

8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt

≥97.0% (HPLC), powder

• Synonym(s): pCPT-cAMP
• 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

Properties

• 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)

Description

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

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Safety Information

• 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