5.00583

(+)-Brefeldin A, Eupenicillium brefeldianum

InSolution, ≥95%, 25 mM in DMSO

• Synonym(s): InSolution (+)-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, (1 S,2 E,7 S,10 E,12 R,13 R,15 S)-12,15-dihydroxy-7-methyl-8-oxabicyclo[11.3.0]hexadeca-2,10-dien-9-one,
• Empirical Formula (Hill Notation): C₁₆H₂₄O₄
• CAS Number: 20350-15-6
• Molecular Weight: 280.36
• MDL number: MFCD12913297
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥95% (HPLC)
• form: liquid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; avoid repeated freeze/thaw cycles; desiccated (hygroscopic); protect from light
• storage temp.: −70°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. Inhibits the activity of BIG1 and BIG2, the guanine-nucleotide exchange proteins for ADP-ribosylation factors. Blocks binding of ADP-ribosylation factor to the Golgi and inhibits the GDP-GTP exchange.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
ADP-ribosylation factor (ARF)

Reversible: yes

Packaging

Packaged under inert gas

Warning

Toxicity: Irritant (B)

Physical form

A 25 mM (2 mg/285 µL) solution of (+)-Brefeldin A (Cat. No. 203729) in DMSO.

Reconstitution

Following initial thaw, aliquot and freeze (-70°C). Aliquots are stable for up to 6 months at -70°C. Use only fresh DMSO for further dilutions prior to use.

Other Notes

Yamagi, R., et al. 2000. Proc. Natl. Acad. Sci. USA97, 2567.
Moriango, N., et al. 1996. Proc. Natl. Acad. Sci. USA93, 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

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 2
• Flash Point(F): 188.6 °F - (refers to pure substance)
• Flash Point(C): 87 °C - (refers to pure substance)