5.00506

EPAC Inhibitor, ESI-09

• Sinónimos: EPAC Inhibitor, ESI-09, 3-(5- tert-butyl-isoxazol-3-yl)-2-((3-chlorophenyl)-hydrazono)-3-oxo-propionitrile, cAMP -GEF Inhibitor, Exchange Protein Directly Activated by cAMP Inhibitor
• Fórmula empírica (notación de Hill): C₁₆H₁₅ClN₄O₂
• Número de CAS: 263707-16-0
• Peso molecular: 330.77
• Número MDL: MFCD00109218
• Código UNSPSC: 12352200
• NACRES: NA.77

Propiedades

• Ensayo: ≥98% (HPLC)
• Nivel de calidad: 100
• Formulario: powder
• fabricante / nombre comercial: Calbiochem^®
• condiciones de almacenamiento: OK to freeze; protect from light
• color: yellow
• solubilidad: DMSO: 100 mg/mL
• temp. de almacenamiento: 2-8°C
• cadena SMILES: Clc1cc(ccc1)N\N=C(\C(=O)c2n[o]c(c2)C(C)(C)C)/C#N
• InChI: 1S/C16H15ClN4O2/c1-16(2,3)14-8-12(21-23-14)15(22)13(9-18)20-19-11-6-4-5-10(17)7-11/h4-8,19H,1-3H3/b20-13+
• Clave InChI: DXEATJQGQHDURZ-DEDYPNTBSA-N

Descripción

Descripción general

A cell-permeable compound that targets cAMP-binding domain of EPAC/cAMP-GEF and inhibits cAMP-dependent EPAC GEF activity (IC₅₀ = 1.4 and 3.2 µM, respectively, against EPAC2 and EPAC1).

A cell-permeable, propionitrile compound that targets the CBD (cAMP-binding domain) of EPAC/cAMP-GEF with 4-fold higher affinity than cAMP (IC₅₀ = 10 vs. 39 µM, respectively, against 8-NBD-cAMP in competition EPAC2 binding assay) and selectively inhibits cAMP-dependent EPAC GEF activity (IC₅₀ = 1.4 and 3.2 µM, respectively, against EPAC2 and EPAC1; [cAMP] = 25 µM) with much reduced potency toward cAMP-dependent PKA activity (10% and 20% inhibition at 100 µM, respectively, against 100 µM cAMP-stimulated Type Iα and IIβ PKA activity). Shown to block both basal and 8-CPT-2′-O-Me-cAMP prodrug 007-AM-stimulated Akt thr308/Ser473 phosphorylations in serum-starved human pancreatic cancer AsPC-1 (%thr308/%Ser473 of basal phosphorylation = 200%/185%, 85%/65%, and <10%/<10%, respectively, with 0, 1, 10 µM ESI-09; [007-AM] = 10 µM) and rat pancreatic β-cell INS-1 without affecting EGF-stimulated Akt phosphorylations, resulting in effective inhibition of EPAC-mediated insulin secretion from INS-1 cells (by 57% and 100%, respectively, at 5 and 10 µM; [007-AM] = 10 µM) and pancreatic cancer cell invasion (~60% inhibition at 5 µM using AsPC-1 and PANC-1 cells).

Envase

Packaged under inert gas

Advertencia

Toxicity: Standard Handling (A)

Reconstitución

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Otras notas

Almahariq, M., et al. 2013. Mol Pharmacol.83, 122.

Información legal

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

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