116812

Adenosine 3′,5′-cyclic Monophosphate, 8-(4-Chlorophenylthio)-, Sodium Salt

Cell-permeable cAMP analog that activates both protein kinase A and protein kinase G.

• Sinónimos: Adenosine 3′,5′-cyclic Monophosphate, 8-(4-Chlorophenylthio)-, Sodium Salt, Adenosine 3ʹ,5ʹ-cyclic Monophosphate, 8-(4-Chlorophenylthio)-, Sodium Salt
• Fórmula empírica (notación de Hill): C₁₆H₁₄ClN₅O₆PS · Na
• Número CAS: 93882-12-3
• Peso molecular: 493.79
• Número MDL: MFCD00057683
• Código UNSPSC: 41106305
• NACRES: NA.77

Propiedades

• Nivel de calidad: 100
• Ensayo: ≥98% (HPLC)
• Formulario: solid
• fabricante / nombre comercial: Calbiochem^®
• condiciones de almacenamiento: OK to freeze; desiccated (hygroscopic)
• color: white
• solubilidad: water: 10 mg/mL
• Condiciones de envío: ambient
• temp. de almacenamiento: −20°C
• cadena SMILES: [Na+].[P]1(=O)(O[C@@H]2[C@H](O[C@H]([C@@H]2O)[n]3c4ncnc(c4nc3Sc5ccc(cc5)Cl)N)CO1)[O-]
• 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
• Clave InChI: YIJFVHMIFGLKQL-DNBRLMRSSA-M

Descripción

Descripción general

Cell-permeable cAMP analog that activates both protein kinase A and protein kinase G. Induces the guanine-nucleotide-exchange factor activity of EGFI, also known as Epac (exchange protein directly activated by cAMP), and EGFII towards Rap1 both in vivo and in vitro. Also acts as a potent inhibitor of cGMP specific phosphodiesterase (IC₅₀ = 900 nM). Also inhibits cAMP-specific phosphodiesterases at much higher concentrations (IC₅₀ = 25 µM).

Acciones bioquímicas o fisiológicas

Cell permeable: yes

Primary Target
Protein kinase A and protein kinase G

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 900 nM against cGMP-specific phosphodiesterase

Nota de preparación

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C

Otras notas

de Rooij, J., et al. 1998. Nature.396, 474.
Kawasaki, H., et al. 1998. Science.282, 2275.
Moed, P.J., et al. 1993. Comp. Biochem. Physiol.105A, 711.
Connolly, B.J., et al. 1992. Biochem. Pharmacol.44, 2303.
Phillips, M.E., and Taylor, A. 1992. J. Physiol.456, 591.
Shipston, M.J., and Antoni, F.A. 1992. Endocrinology130, 2213.
Datta, R., et al. 1991. Blood78, 83.
Peters, D.J.M., et al. 1991. Proc. Natl. Acad. Sci. USA88, 9219.
Sandberg, M., et al. 1991. Biochem. J.279, 521.
Unterman, T.G., et al. 1991. Endocrinology128, 2693.
Xu, H., et al. 1989. Brain Res.504, 36.

Información legal

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Cláusula de descargo de responsabilidad

Toxicity: Standard Handling (A)

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable