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
• Empirical Formula (Hill Notation): C₁₆H₂₄O₄
• CAS Number: 20350-15-6
• Molecular Weight: 280.36
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD12913297
• Assay: ≥95% (HPLC)
• Form: crystalline solid
• Storage condition: OK to freeze

Properties

• 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.
• description: Merck USA index - 14, 1369
• Quality Segment: 100
• 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
• 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

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).

Biochem/physiol Actions

Cell permeable: no

Primary Target
Blocks translocation of proteins from the endoplasmic reticulum (ER) to the Golgi apparatus

Product does not compete with ATP.

Reversible: yes

Preparation Note

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

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.

Legal Information

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

Disclaimer

Toxicity: Harmful (C)

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: P264 - P270 - P301 + P310 - P405 - P501
• 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