Brefeldin A

Brefeldin A
IUPAC name

(1R,​2E,​6S,​10E,​11aS,​13S,​14aR)-​1,​13-​dihydroxy-​6-​methyl-​1,​6,​7,​8,​9,​11a,​12,​13,​14,​14a-​decahydro-​4H-​cyclopenta​[f]oxacyclotridecin-​4-one
Other names

γ,4- Dihydroxy- 2-(6-hydroxy-1-heptenyl)- 4-cyclopentanecrotonic acid λ-lactone
Identifiers
CAS number 20350-15-6 Y
PubChem 5287620
ChemSpider 4449949 Y
DrugBank DB07348
ChEBI CHEBI:48080 Y
ChEMBL CHEMBL19980
Jmol-3D images Image 1
Properties
Molecular formula C16H24O4
Molar mass 280.36 g mol−1
Appearance White to off-white crystalline powder
Melting point

204–205 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Brefeldin A is a lactone antibiotic produced by fungal organisms such as Eupenicillium brefeldianum. Brefeldin A inhibits transport of proteins from ER to Golgi and induces retrograde protein transport from the Golgi apparatus to the endoplasmic reticulum. This leads to proteins accumulating inside the ER. In mammalian and yeast cells, the main target of brefeldin A appears to be a certain type of GTP-exchange factors responsible for activating a GTPase called Arf1p ; in turn, Arf1p is involved in the formation of transport vesicles by recruiting coat proteins to intracellular membranes. Brefeldin A was initially isolated as an anti-viral antibiotic[1] but is now primarily used in biological research to study protein transport.

Physical data

[2]

Brefeldin A affects COPI coat formation, which is involved in retrograde transport. It inhibits ArfI activation, prohibiting recruitment of COPI coat proteins to the budding vesicle by binding to its guanine exchange factor.

References

  1. ^ Tamura G, Ando K, Suzuki S, Takatsuki A, Arima K (February 1968). "Antiviral activity of brefeldin A and verrucarin A". J. Antibiot. 21 (2): 160–1. PMID 4299889. 
  2. ^ Physical data source: Brefeldin A product page from Fermentek

External links