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Merck

203729

Brefeldin A

Specifically and reversibly blocks translocation of proteins from the endoplasmic reticulum (ER) to the Golgi apparatus without affecting endocytosis or lysosome function.

Synonym(s):

(+)-Brefeldin A, Eupenicillium brefeldianum, 1,6,7,8,9,11a,12,13,14,14a-Decahydro-1,13-dihydroxy-6-methyl-4H-cyclopent[f]oxacyclotridecin-4-one

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About This Item

Empirical Formula (Hill Notation):
C16H24O4
CAS Number:
20350-15-6
Molecular Weight:
280.36
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD12913297

Product Name

(+)-Brefeldin A, Eupenicillium brefeldianum, Specifically and reversibly blocks translocation of proteins from the endoplasmic reticulum (ER) to the Golgi apparatus without affecting endocytosis or lysosome function.

SMILES string

O1[C@H](CCC\C=C\[C@H]2[C@H]([C@H](\C=C\C1=O)O)C[C@H](C2)O)C

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-PNFJWZTBSA-N

description

Merck USA index - 14, 1369

assay

≥95% (HPLC)

form

crystalline solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

white

solubility

methanol: 2 mg/mL

shipped in

ambient

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Reversible: yes
Primary Target
Blocks translocation of proteins from the endoplasmic reticulum (ER) to the Golgi apparatus
Product does not compete with ATP.
Cell permeable: no

Disclaimer

Toxicity: Harmful (C)

General description

Specifically and reversibly blocks translocation of proteins from the endoplasmic reticulum (ER) to the Golgi apparatus without affecting endocytosis or lysosome function. Inhibitor of HDL-mediated cholesterol efflux. Causes disassembly of the Golgi complex and ER swelling in a variety of mammalian cell lines at <40 ng/ml. Blocks binding of ADP-ribosylation factor to the Golgi and inhibits the GDP-GTP exchange. Inhibits the activity of BIG1 and BIG2, the guanine-nucleotide exchange proteins for ADP-ribosylation factors. Also available as a 25 mM solution in DMSO (Cat. No. 500583).

Other Notes

Yamagi, R., et al. 2000. Proc. Natl. Acad. Sci. USA 97, 2567.
Moriango, N., et al. 1996. Proc. Natl. Acad. Sci. USA 93, 12856.
Mendez, A.J. 1995. J. Biol. Chem. 270, 5891.
Ridgway, N.D., et al. 1995. J. Biol. Chem. 270, 8023.
Tsai, S.C., et al. 1994. Proc. Natl. Acad. Sci. USA91, 3063.
Ktistakis, N.Y., et al. 1992. Nature356, 344.

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for 2 months at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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