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B6542

Sigma-Aldrich

Brefeldin A

≥99% (HPLC and TLC), BioXtra, for molecular biology

Synonym(s):
BFA, Cyanein, Ascotoxin, γ,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone, Decumbin
Empirical Formula (Hill Notation):
C16H24O4
CAS Number:
Molecular Weight:
280.36
Beilstein:
25191
MDL number:
PubChem Substance ID:
NACRES:
NA.52

Quality Level

biological source

Penicillium brefeldianum

grade

for molecular biology

product line

BioXtra

assay

≥99% (HPLC and TLC)

form

powder

solubility

DMSO: 10 mg/mL (Store stock solutions at -20 °C)

Mode of action

protein synthesis | interferes

antibiotic activity spectrum

neoplastics

storage temp.

2-8°C

SMILES string

C[C@H]1CCC\C=C\[C@@H]2C[C@H](O)C[C@H]2[C@H](O)\C=C\C(=O)O1

InChI

1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4+,8-7+/t11-,12+,13-,14+,15+/m0/s1

InChI key

KQNZDYYTLMIZCT-KQPMLPITSA-N

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General description

Brefeldin induces ADP-ribosylation of CtBP1/BARS protein that regulates the intracellular trafficking and movement of secretory proteins from endoplasmic reticulum to Golgi apparatus.
Chemical structure: macrolide

Application

Suitable for molecular biology studies of secretory proteins and mechanisms of intracellular transport

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

Brefeldin A (BFA) is a fungal metabolite which disrupts the structure and function of the Golgi apparatus. BFA is an activator of the sphingomyelin cycle. Brefeldin A-mediated apoptosis has been observed in human tumor cells.

Principle

Brefeldin is a fungal metabolite that disrupts protein secretion in eukaryotic cells by disrupting the Golgi apparatus. It does not affect the process of protein synthesis.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

More documents

Quotes and Ordering

Y Misumi et al.
The Journal of biological chemistry, 261(24), 11398-11403 (1986-08-25)
We examined the effect of brefeldin A, an antiviral antibiotic, on protein synthesis, intracellular processing, and secretion in primary culture of rat hepatocytes. The secretion was strongly blocked by the drug at 1 microgram/ml and higher concentrations, while the protein
Marco Lepore et al.
Nature communications, 5, 3866-3866 (2014-05-17)
Mucosal-associated invariant T (MAIT) cells are abundant in humans and recognize conserved bacterial antigens derived from riboflavin precursors, presented by the non-polymorphic MHC class I-like molecule MR1. Here we show that human MAIT cells are remarkably oligoclonal in both the
Laura Jeanbart et al.
Cancer immunology research, 2(5), 436-447 (2014-05-06)
The sentinel or tumor-draining lymph node (tdLN) serves as a metastatic niche for many solid tumors and is altered via tumor-derived factors that support tumor progression and metastasis. tdLNs are often removed surgically, and therapeutic vaccines against tumor antigens are
Anniek B van der Waart et al.
Blood, 124(23), 3490-3500 (2014-10-23)
Effective T-cell therapy against cancer is dependent on the formation of long-lived, stem cell-like T cells with the ability to self-renew and differentiate into potent effector cells. Here, we investigated the in vivo existence of stem cell-like antigen-specific T cells
Julian H Elliott et al.
PLoS pathogens, 10(10), e1004473-e1004473 (2014-11-14)
Human immunodeficiency virus (HIV) persistence in latently infected resting memory CD4+ T-cells is the major barrier to HIV cure. Cellular histone deacetylases (HDACs) are important in maintaining HIV latency and histone deacetylase inhibitors (HDACi) may reverse latency by activating HIV

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