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).

• Synonim(y): Berberine chloride form, Berberine, Natural Yellow 18
• Wzór empiryczny (zapis Hilla): C₂₀H₁₈ClNO₄
• Numer CAS: 633-65-8
• Masa cząsteczkowa: 371.81
• Numer w indeksie barw: 75160
• Beilstein: 3836585
• Numer MDL: MFCD00011939
• Kod UNSPSC: 12352200

Właściwości

• Poziom jakości: 100
• Próba: ≥95% (NMR if no UV signal, HPLC)
• Postać: powder
• producent / nazwa handlowa: Calbiochem^®
• warunki przechowywania: OK to freeze; protect from light
• kolor: yellow
• rozpuszczalność: water: 1 mg/mL; DMSO: 10 mg/mL
• Warunki transportu: ambient
• temp. przechowywania: 2-8°C
• ciąg 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
• Klucz InChI: VKJGBAJNNALVAV-UHFFFAOYSA-M

Opis

Opis ogólny

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.

Zastosowanie

Fluorescent stain for heparin in mast cells

Działania biochem./fizjol.

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.

Opakowanie

Packaged under inert gas

Ostrzeżenie

Toxicity: Standard Handling (A)

Inne uwagi

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.

Informacje prawne

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

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Informacja o środkach bezpieczeństwa

• Kod klasy składowania: 11 - Combustible Solids
• Klasa zagrożenia wodnego (WGK): WGK 2
• Temperatura zapłonu (°F): Not applicable
• Temperatura zapłonu (°C): Not applicable