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B5936

Brefeldin A

Name: Brefeldin A
Brand: SIGMA

Ready Made Solution, from Penicillium brefeldianum, 10 mg/mL in DMSO

Synonym(s):

Synergisidin, 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

UNSPSC Code:

51102829

NACRES:

NA.85

PubChem Substance ID:

329773270

MDL number:

MFCD12913297

Beilstein/REAXYS Number:

25191

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biological source

Penicillium brefeldianum

Quality Level

200

vapor pressure

0.56 hPa ( 20 °C)

form

ready-to-use solution

autoignition temp.

301 °C

concentration

10 mg/mL in DMSO

solubility

DMSO: 10 mg/mL

antibiotic activity spectrum

neoplastics

application(s)

advanced drug delivery

mode of action

cell membrane | interferes

shipped in

wet ice

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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Related Categories

Chemistry & Biochemicals

Antibiotics

Biochemicals

Cell Culture Supplements & Reagents

Application

Brefeldin A produced from Penicillium brefeldianum may be used to study protein and lipid transport between Golgi complex and the cell surface.

Biochem/physiol Actions

Brefeldin A (BFA) is a fungal metabolite which disrupts the structure and function of the Golgi apparatus by inhibiting transport of proteins from ER to Golgi and inducing retrograde protein transport from the Golgi apparatus to the endoplasmic reticulum. BFA inhibits the transport of sphingomyelin to the surface of mammalian cells. The ester derivatives of BFA exhibit anti-cancer properties.

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.

Disrupts the structure and function of the Golgi apparatus; activator of the sphingomyelin cycle.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Store under inert gas. Hygroscopic.Storage class (TRGS 510): Combustible liquids

Storage Class

10 - Combustible liquids

flash_point_f

188.6 °F - closed cup

flash_point_c

87 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, multi-purpose combination respirator cartridge (US)

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Transport of sphingomyelin to the cell surface is inhibited by brefeldin A and in mitosis, where C6-NBD-sphingomyelin is translocated across the plasma membrane by a multidrug transporter activity.

A van Helvoort et al.

Journal of cell science, 110 ( Pt 1), 75-83 (1997-01-01)

Sphingomyelin is a major lipid of the mammalian cell surface. The view that sphingomyelin, after synthesis in the Golgi lumen, reaches the outer leaflet of the plasma membrane on the inside of carrier vesicles has been challenged by inconsistencies in

Antiviral activity of brefeldin A and verrucarin A.

G Tamura et al.

The Journal of antibiotics, 21(2), 160-161 (1968-02-01)

Parallel T-cell cloning and deep sequencing of human MAIT cells reveal stable oligoclonal TCRβ repertoire.

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

Airway epithelial SPDEF integrates goblet cell differentiation and pulmonary Th2 inflammation.

Priya Rajavelu et al.

The Journal of clinical investigation, 125(5), 2021-2031 (2015-04-14)

Epithelial cells that line the conducting airways provide the initial barrier and innate immune responses to the abundant particles, microbes, and allergens that are inhaled throughout life. The transcription factors SPDEF and FOXA3 are both selectively expressed in epithelial cells

A CREB3-ARF4 signalling pathway mediates the response to Golgi stress and susceptibility to pathogens.

Jan H Reiling et al.

Nature cell biology, 15(12), 1473-1485 (2013-11-05)

Treatment of cells with brefeldin A (BFA) blocks secretory vesicle transport and causes a collapse of the Golgi apparatus. To gain more insight into the cellular mechanisms mediating BFA toxicity, we conducted a genome-wide haploid genetic screen that led to

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Global Trade Item Number

SKU	GTIN
B5936-200UL	04061833434314

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