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B3251 Sigma

Berberine chloride form

Synonym: Natural Yellow 18

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Description

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

5, 10, 25 g in glass bottle

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Berberine chloride

European Pharmacopoeia (EP) Reference Standard

Berberine chloride hydrate

technical, ≥90% (AT)

Safety & Documentation

Safety Information

WGK Germany 
2

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Determination of Water Content in Berberine chloride Using Karl Fischer Titration

Berberine chloride does not dissolve in the alcoholic media of the KF titration. Nevertheless the whole water can be extracted completely. Addition of formamide helps to dissolve the sample, but a pr...
Keywords: Pharmaceutical, Precipitation, Titrations

Drug Transport

Protein-based drug transporters are found in most tissues including liver, kidney, intestine, and brain. Because of their complexity and genetic heterogeneity, these proteins are often produced as re...
Robert Gates
Biofiles Volume 6 Article 1
Keywords: Absorption, Anti-inflammatory agents, Antibiotics, Antimicrobials, Apoptosis, Cancer, Catalog, Cytotoxins, Detoxification, Enzyme-linked immunosorbent assay, Gene expression, Genetic, High performance liquid chromatography, Immunohistochemistry, Mass spectrometry, Metabolites, Methods, Phosphorylations, Separation, The Reporter, Transfection, Type, Western blot

Peer-Reviewed Papers

References

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Membrane transporters in drug development Giacomini, K.M., et al. Nat. Rev. Drug Discov. 9, 215-236, (2010)

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Imaging of Plasmodium liver stages to drive next-generation antimalarial drug discovery. Stephan Meister et al Science 334, 1372-7, (2011)

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Inhibitors of prolyl oligopeptidases for the therapy of human diseases: defining diseases and inhibitors. Lawandi J, Gerber-Lemaire S, Juillerat-Jeanneret L, Moitessier N. J. Med. Chem. 53, 3423-3438, (2010)

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Metabolites of the "smoke tree", Dalea spinosa, potentiate antibiotic activity against multidrug-resistant Staphylococcus aureus. Gil Belofsky et al J. Nat. Prod. 69, 261-4, (2006)

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Berberine-INF55 (5-nitro-2-phenylindole) hybrid antimicrobials: effects of varying the relative orientation of the berberine and INF55 components. Danuta Tomkiewicz et al Antimicrob. Agents Chemother. 54, 3219-24, (2010)

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Degradation Of MDM2 By The Interaction Between Berberine And DAXX Leads To Potent Apoptosis In MDM2-Overexpressing Cancer Cells. Zhang, X., et al. Cancer Res. 70, 9895-904, (2010)

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Functional cloning and characterization of the multidrug efflux pumps NorM from Neisseria gonorrhoeae and YdhE from Escherichia coli. Feng Long et al Antimicrob. Agents Chemother. 52, 3052-60, (2008)

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Aaptamines as sortase A inhibitors from the tropical sponge Aaptos aaptos. Kyoung Hwa Jang et al Bioorg. Med. Chem. Lett. 17, 5366-9, (2007)

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9-Substituted berberine derivatives as G-quadruplex stabilizing ligands in telomeric DNA. Wan-Jin Zhang et al Bioorg. Med. Chem. 15, 5493-501, (2007)

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Probing of the cis-5-phenyl proline scaffold as a platform for the synthesis of mechanism-based inhibitors of the Staphylococcus aureus sortase SrtA isoform. Konstantin V Kudryavtsev et al Bioorg. Med. Chem. 17, 2886-93, (2009)

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The dynamics of mast cell secretion studied by vital berberine staining. Berlin, G. and Enerback, L. Agents Actions 14, 401, (1984)

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The fluorescent staining of heparin in mast cells using berberine sulfate: compatibility with paraformaldehyde or o-phthalaldehyde induced fluorescence and metachromasia. Dimlich, R.V.W., et al. Stain Technol. 55, 217, (1980)

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Structural mechanisms of QacR induction and multidrug recognition. Schumacher, M.A., et al. Science 294, 2158, (2001)

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Up-regulation of multidrug resistance transporter expression by berberine in human and murine hepatoma cells. Lin, H.L., et al. Cancer 85, 1937-1942, (1999)

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Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity. Ki Hyun Kim et al Bioorg. Med. Chem. Lett. 20, 4487-90, (2010)

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Antibacterial activity of berberine-NorA pump inhibitor hybrids with a methylene ether linking group. Siritron Samosorn et al Bioorg. Med. Chem. 17, 3866-72, (2009)

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Synthesis, biological evaluation, and molecular modeling of berberine derivatives as potent acetylcholinesterase inhibitors. Ling Huang et al Bioorg. Med. Chem. 18, 1244-51, (2010)

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Synthesis, biological evaluation and molecular modeling of novel triazole-containing berberine derivatives as acetylcholinesterase and ?-amyloid aggregation inhibitors. Anding Shi et al Bioorg. Med. Chem. 19, 2298-305, (2011)

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Quinolino-benzo-[5, 6]-dihydroisoquindolium compounds derived from berberine: a new class of highly selective ligands for G-quadruplex DNA in c-myc oncogene. Yan Ma et al Eur. J. Med. Chem. 46, 1906-13, (2011)

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9-N-Substituted berberine derivatives: stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc. Y. Ma. et al., Bioorg. Med. Chem. 16, 7582-7591, (2008)

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Berberine analogues as a novel class of the low-density-lipoprotein receptor up-regulators: synthesis, structure-activity relationships, and cholesterol-lowering efficacy. Ying-Hong Li et al J. Med. Chem. 52, 492-501, (2009)

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Phytochemistry and antifungal properties of the newly discovered tree Pleodendron costaricense. Virginie Treyvaud Amiguet et al J. Nat. Prod. 69, 1005-9, (2006)

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Synthesis of linked berberine dimers and their remarkably enhanced DNA-binding affinities. Wen-Hua Chen et al Bioorg. Med. Chem. Lett. 15, 2689-92, (2005)

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Benzenediol-berberine hybrids: Multifunctional agents for Alzheimer's disease. Huailei Jiang et al Bioorg. Med. Chem. 19, 7228-35, (2011)

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Synthesis of 9-substituted derivatives of berberine as anti-HIV agents. Hardik S Bodiwala et al Eur. J. Med. Chem. 46, 1045-9, (2011)

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Synthesis and biological evaluation of a new series of berberine derivatives as dual inhibitors of acetylcholinesterase and butyrylcholinesterase. Ling Huang et al Bioorg. Med. Chem. 18, 4475-84, (2010)

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Structure-activity relationships of 2-aryl-1H-indole inhibitors of the NorA efflux pump in Staphylococcus aureus. Joseph I Ambrus et al Bioorg. Med. Chem. Lett. 18, 4294-7, (2008)

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Synthesis and evaluation of 9-O-substituted berberine derivatives containing aza-aromatic terminal group as highly selective telomeric G-quadruplex stabilizing ligands. Yan Ma et al Bioorg. Med. Chem. Lett. 19, 3414-7, (2009)

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Discovery of estrogen receptor ? modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells. Li Liu et al Bioorg. Med. Chem. Lett. 22, 154-63, (2012)

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Synthesis and structure-activity relationships of novel, substituted 5,6-dihydrodibenzo[a,g]quinolizinium P2X7 antagonists. Ga Eun Lee et al Bioorg. Med. Chem. Lett. 19, 954-8, (2009)

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Antiviral activity of berberine and related compounds against human cytomegalovirus. Kyoko Hayashi et al Bioorg. Med. Chem. Lett. 17, 1562-4, (2007)

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Berberine derivatives, with substituted amino groups linked at the 9-position, as inhibitors of acetylcholinesterase/butyrylcholinesterase. Ling Huang et al Bioorg. Med. Chem. Lett. 20, 6649-52, (2010)

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Neovibsanin F and its congeners, rearranged vibsane-type diterpenes from Viburnum suspensum. Yoshiyasu Fukuyama et al J. Nat. Prod. 69, 1098-100, (2006)

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Synthesis and biological evaluation of berberine analogues as novel up-regulators for both low-density-lipoprotein receptor and insulin receptor. Yan-Xiang Wang et al Bioorg. Med. Chem. Lett. 19, 6004-8, (2009)

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Synthesis, anticancer and antioxidant activities of 7-methoxyisoflavanone and 2,3-diarylchromanones. Kanagasabai Kanagalakshmi et al Eur. J. Med. Chem. 45, 2447-52, (2010)

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Synthesis of 13-(substituted benzyl) berberine and berberrubine derivatives as antifungal agents. Ki Duk Park et al Bioorg. Med. Chem. Lett. 16, 3913-6, (2006)

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Design, synthesis, and cholesterol-lowering efficacy for prodrugs of berberrubine. Ying-Hong Li et al Bioorg. Med. Chem. 18, 6422-8, (2010)

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Selective cholinesterase inhibition by lanostane triterpenes from fruiting bodies of Ganoderma lucidum. Iksoo Lee et al Bioorg. Med. Chem. Lett. 21, 6603-7, (2011)

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Differential gene expression in rat vascular smooth muscle cells following treatment with coptisine exerts a selective antiproliferative effect. Hiroka Suzuki et al J. Nat. Prod. 74, 634-8, (2011)

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Structure-activity relationship of isoform selective inhibitors of Rac1/1b GTPase nucleotide binding. Eric Beausoleil et al Bioorg. Med. Chem. Lett. 19, 5594-8, (2009)

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Synthesis and structure-activity relationships of berberine analogues as a novel class of low-density-lipoprotein receptor up-regulators. Peng Yang et al Bioorg. Med. Chem. Lett. 18, 4675-7, (2008)

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In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen. David Plouffe et al Proc. Natl. Acad. Sci. U. S. A. 105, 9059-64, (2008)

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Synthesis and antihyperglycemic evaluation of various protoberberine derivatives. Xiaoli Bian et al Bioorg. Med. Chem. Lett. 16, 1380-3, (2006)

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Analysis of physico-chemical properties of substrates of ABC and MFS multidrug transporters of pathogenic Candida albicans. Nidhi Puri et al Eur. J. Med. Chem. 45, 4813-26, (2010)

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Antioxidant and cytotoxic activities of canadine: biological effects and structural aspects. Estela R Correché et al Bioorg. Med. Chem. 16, 3641-51, (2008)

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Beil. 27,II,567

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