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B3251

Sigma-Aldrich

Berberine chloride form

Synonyme(s) :

Benzodioxide, Berberine HCl, Natural Yellow 18

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About This Item

Formule empirique (notation de Hill):
C20H18ClNO4
Numéro CAS:
633-65-8
Poids moléculaire :
371.81
Numéro C.I. (Colour Index):
75160
Numéro Beilstein :
3836585
Numéro CE :
211-195-9
Numéro MDL:
MFCD00011939
Code UNSPSC :
12171500
ID de substance PubChem :
24891691
Nomenclature NACRES :
NA.32

Forme

powder

Niveau de qualité

200

Solubilité

methanol: soluble

Chaîne 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

Clé InChI

VKJGBAJNNALVAV-UHFFFAOYSA-M

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Description générale

Berberine Chloride form or Natural Yellow 18, is also known as 5,6-dihydro-9,10-dimethoxybenzo(g)-1,3-benzodioxolo (5,6-a) quinolizinium is a benzyl tetra isoquinoline plant alkaloid. Berberine contains a quaternary base and is commercially available in berberine chloride form.

Application

Berberine Chloride is a fluorescent stain used to stain heparin in mast cells. Berberine upregulates the expression of Pgp in hepatoma cells.
Fluorescent stain for heparin in mast cells

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Canadine phyproof® Reference Substance

PHL80378

Canadine

BERBERINE ACETONE ADDUCT AldrichCPR

S567574

BERBERINE ACETONE ADDUCT

Hydrastine phyproof® Reference Substance

PHL89511

Hydrastine

Dihydroberberine phyproof® Reference Substance

PHL80429

Dihydroberberine

BERBERINE BISULFATE AldrichCPR

S583634

BERBERINE BISULFATE

Wan-Jin Zhang et al.
Bioorganic & medicinal chemistry, 15(16), 5493-5501 (2007-06-19)
The interaction of berberine and its 9-substituted derivatives with human telomeric DNA d[G(3)(T(2)AG(3))(3)](telo21) has been investigated via CD spectroscopy, fluorescence spectroscopy, PCR-stop assay, competitive dialysis, and telomerase repeat amplification protocol (TRAP) assay. The results indicated that these semisynthesized compounds could
Xiaoling Zhang et al.
Cancer research, 70(23), 9895-9904 (2010-10-12)
Berberine, a natural product derived from a plant used in Chinese herbal medicine, is reported to exhibit anticancer effects; however, its mechanism of action is not clearly defined. Herein, we demonstrate that berberine induces apoptosis in acute lymphoblastic leukemia (ALL)
Ying-Hong Li et al.
Journal of medicinal chemistry, 52(2), 492-501 (2008-12-19)
Twenty-nine derivatives of berberine (1) or pseudoberberine (2) were designed, semisynthesized, and evaluated for their up-regulatory activity on the low-density-lipoprotein receptor (LDLR) expression. SAR analysis revealed that (i) the methylenedioxy group at the 2- and 3-position is an essential element
Anding Shi et al.
Bioorganic & medicinal chemistry, 19(7), 2298-2305 (2011-03-15)
A series of novel triazole-containing berberine derivatives were synthesized via the azide-alkyne cycloaddition reaction. Their biological activity as inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. Among them, compound 16d, which featured a diisopropylamino substitution at the 4-position
Yan Ma et al.
Bioorganic & medicinal chemistry, 16(16), 7582-7591 (2008-08-05)
A series of 9-N-substituted berberine derivatives (2a-j) were synthesized and evaluated as a new class of G-quadruplex binding ligands. G-quadruplex of DNA had been proven to be the transcription controller of human c-myc gene. The interaction of 9-N-substituted berberine derivatives
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