Bengamide B

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Cat.No. 5273 - Bengamide B | C32H58N2O8 | CAS No. 104947-69-5
Description: Potent inhibitor of NF-κB activation
Chemical Name: (6E)-6,7,8,9-Tetradeoxy-N-[(3S,6S)-hexahydro-1-methyl-2-oxo-6-[(1-oxotetradecyl)oxy]-1H-azepin-3-yl]-8-methyl-2-O-methyl-D-gulo-Non-6-enonamide
Purity: ≥97% (HPLC)
Literature (3)
Pathways (1)

Biological Activity

Potent inhibitor of NF-κB activation (IC50 = 85 nM); decreases IκBα phosphorylation. Attenuates LPS-induced nitric oxide production and expression of TNF-α, IL-6 and MCP. Suppresses proliferation of HeLa and HCT116 cells. Anti-inflammatory and antitumor.

Technical Data

M. Wt 598.81
Formula C32H58N2O8
Storage Store at -20°C
Purity ≥97% (HPLC)
CAS Number 104947-69-5
PubChem ID 6444128
Smiles O=C1N(C)C[C@@H](OC(CCCCCCCCCCCCC)=O)CC[C@@H]1NC([C@H](OC)[C@H](O)[C@@H](O)[C@H](O)/C=C/C(C)C)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
DMSO 1 2

Preparing Stock Solutions

The following data is based on the product molecular weight 598.81. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.02 mM 83.5 mL 417.49 mL 834.99 mL
0.1 mM 16.7 mL 83.5 mL 167 mL
0.2 mM 8.35 mL 41.75 mL 83.5 mL
1 mM 1.67 mL 8.35 mL 16.7 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References are publications that support the biological activity of the product.

Hu et al (2007) Regulation of c-Src nonreceptor tyrosine kinase activity by bengamide A through inhibition of methionine aminopeptidases. Chem.Biol. 14 764 PMID: 17656313

Johnson et al (2012) Myxobacteria versus sponge-derived alkaloids: the bengamide family identified as potent immune modulating agents by scrutiny of LC-MS/ELSD libraries. Bioorg.Med.Chem. 20 4348 PMID: 22705020

Kinder et al (2001) Synthesis and antitumor activity of ester-modified analogues of bengamide B. J.Med.Chem. 44 3692 PMID: 11606134

If you know of a relevant reference for Bengamide B, please let us know.

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View all NF-κB and IκB Inhibitors

Keywords: Bengamide B, Bengamide B supplier, Methionyl, aminopeptidase, MetAP1, MetAP2, potent, NF-κB, inhibitors, nuclear, factor, kappa, B, anti-inflammatory, antitumor, antitumour, inhibits, NF-kB/IkB, 5273, Tocris Bioscience

Citations for Bengamide B

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Literature in this Area

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Pathways for Bengamide B


NF-κB Signaling Pathway

NF-κB signaling plays an important role in inflammation, the innate and adaptive immune response and stress. Dysregulated signaling can occur in inflammatory and autoimmune diseases.