200275

Berberine Chloride

A highly potent and selective oxysterol EBI2 (GPR183) agonist (K_d) = 450 pM in a saturation binding assay, and EC₅₀ = 140 pM over EC₅₀ = 2.1 nM for its enantiomer, 7β,25-OHC, in a GTP-γS binding assay).

• Sinónimos: Berberine chloride form, Berberine, Natural Yellow 18
• Fórmula empírica (notación de Hill): C₂₀H₁₈ClNO₄
• Número de CAS: 633-65-8
• Peso molecular: 371.81
• Número de índice de color: 75160
• Beilstein: 3836585
• Número MDL: MFCD00011939
• Código UNSPSC: 12352200

Propiedades

• Nivel de calidad: 100
• Ensayo: ≥95% (NMR if no UV signal, HPLC)
• Formulario: powder
• fabricante / nombre comercial: Calbiochem^®
• condiciones de almacenamiento: OK to freeze; protect from light
• color: yellow
• solubilidad: water: 1 mg/mL; DMSO: 10 mg/mL
• Condiciones de envío: ambient
• temp. de almacenamiento: 2-8°C
• cadena SMILES: COC1=C(C=[N+](CCC2=C3C=C4C(OCO4)=C2)C3=C5)C5=CC=C1OC.[Cl-]
• InChI: 1S/C20H18NO4.ClH/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2;/h3-4,7-10H,5-6,11H2,1-2H3;1H/q+1;/p-1
• Clave InChI: VKJGBAJNNALVAV-UHFFFAOYSA-M

Descripción

Descripción general

A highly potent and selective oxysterol EBI2 (GPR183) agonist (K_d) = 450 pM in a saturation binding assay, and EC₅₀ = 140 pM over EC₅₀ = 2.1 nM for its enantiomer, 7β,25-OHC, in a GTP-γS binding assay). Dose-dependently suppresses forskolin-induced cAMP accumulation in an EBI2-expressing SK-N-MC/CRE-β-galactosidase cell line (IC₅₀ = 2 nM), but not in control cells. Stimulates migration of LPS-activated spleen B-cells and anti-CD3/CD28-activated CD4⁺ T-cells in a dose-dependent manner. In addition, pharmacological inhibition of its biosynthesis in vivo by Clotrimazole, a CYP7B1inhibitor, promotes the migration of adoptively transferred pre-activated B cells to the T/B boundary, mimicking the phenotype of pre-activated B cells in EBI2-deficient mice.

Aplicación

Fluorescent stain for heparin in mast cells

Acciones bioquímicas o fisiológicas

An alkaloid with weak antibiotic properties. Substrate for MDR efflux pumps. Antimicrobial activities of berberine is potentiated by the MDR inhibitor 5´-methoxyhydnocarpin (5´-MHC). Berberine upregulates the expression of Pgp in hepatoma cells. Treatment with berberine potentially results in the reduced accumulation of chemotherapeutic drugs.

Envase

Packaged under inert gas

Advertencia

Toxicity: Standard Handling (A)

Otras notas

Kinm. B., et al. 2011, Brit. Journ. Pharm.164, 106.
Kong, W., et al. 2004, Nature Med.10, 1344.
Dimlich, R. et al. 1980, Stain Technol.55, 217.

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 2
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable