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200275

Berberine Chloride

Name: Berberine Chloride
Brand: MM

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).

Synonym(s):

Berberine chloride form, Berberine, Natural Yellow 18

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₁₈ClNO₄

CAS Number:

633-65-8

Molecular Weight:

371.81

UNSPSC Code:

12352200

Beilstein/REAXYS Number:

3836585

Colour Index Number:

75160

MDL number:

MFCD00011939

Assay:

≥95% (NMR if no UV signal, HPLC)

Form:

powder

Storage condition:

OK to freeze, protect from light

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Properties

Quality Segment

100

assay

≥95% (NMR if no UV signal, HPLC)

form

powder

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

yellow

solubility

water: 1 mg/mL, DMSO: 10 mg/mL

shipped in

ambient

storage temp.

2-8°C

SMILES string

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

InChI key

VKJGBAJNNALVAV-UHFFFAOYSA-M

Description

General description

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.

Application

Fluorescent stain for heparin in mast cells

Biochem/physiol Actions

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.

Packaging

Packaged under inert gas

Other Notes

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.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

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Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c