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B7651

Sigma-Aldrich

Brefeldin A

from Penicillium brefeldianum, ≥99% (HPLC and TLC), powder, activator of the sphingomyelin cycle

Synonym(s):

Nectrolide, γ,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone, Ascotoxin, BFA, Cyanein, Decumbin

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About This Item

Empirical Formula (Hill Notation):
C16H24O4
CAS Number:
20350-15-6
Molecular Weight:
280.36
Beilstein/REAXYS Number:
25191
MDL number:
MFCD12913297
UNSPSC Code:
12352200
PubChem Substance ID:
24278285
NACRES:
NA.77

product name

Brefeldin A, from Penicillium brefeldianum, ≥99% (HPLC and TLC)

biological source

Penicillium brefeldianum

Quality Level

300

assay

≥99% (HPLC and TLC)

form

powder

solubility

DMSO: 10 mg/mL

antibiotic activity spectrum

neoplastics

mode of action

protein synthesis | interferes

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 A (BFA) is a fungal metabolite containing a 13-membered macrocyclic lactone ring. It inhibits protein and nucleic acid synthesis. BFA blocks the exchange of GDP for GTP on adenosine ribosylation factors (ARFs), thereby hindering the binding of coat protein (β-COP) and consequently 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. Brefeldin A has been shown to increase CRISPR-mediated homology-directed repair (HDR) efficiency. It demonstrates a diverse array of biological functions, including antitumor, antiviral, antibiotic, antimitotic, antifungal and antinematodal properties.

Application

Brefeldin A has been used to:



  • increase CRISPR genome editing efficiency.
  • facilitate the measurement of cytokine production
  • block intracellular transports in cell culture experiments

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.
Brefeldin A has been shown to increase CRISPR-mediated homology-directed repair (HDR) efficiency.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Emma M Haapaniemi et al.
Blood, 125(4), 639-648 (2014-10-29)
The signal transducer and activator of transcription (STAT) family of transcription factors orchestrate hematopoietic cell differentiation. Recently, mutations in STAT1, STAT5B, and STAT3 have been linked to development of immunodysregulation polyendocrinopathy enteropathy X-linked-like syndrome. Here, we immunologically characterized 3 patients
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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