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Merck

B5936

Brefeldin A

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

Sinónimos:

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

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Fórmula empírica (notación de Hill):
C16H24O4
Número CAS:
Peso molecular:
280.36
UNSPSC Code:
51102829
NACRES:
NA.85
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
25191
Servicio técnico
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biological source

Penicillium brefeldianum

Quality Level

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

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


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Clase de almacenamiento

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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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)
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



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SKUGTIN
B5936-200UL04061833434314