5.00583

(+)-Brefeldin A, Eupenicillium brefeldianum

InSolution, ≥95%, 25 mM in DMSO

• Synonym(e): 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,
• Empirische Formel (Hill-System): C₁₆H₂₄O₄
• CAS-Nummer: 20350-15-6
• Molekulargewicht: 280.36
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD12913297
• Assay: ≥95% (HPLC)
• Form: liquid
• Storage condition: OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light

Eigenschaften

• Quality Segment: 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
• 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

Beschreibung

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

Preparation Note

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

Disclaimer

Toxicity: Irritant (B)

Sicherheitshinweise

• Lagerklasse: 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)