Brefeldin A
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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
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| Other names
γ,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone
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3D model (JSmol)
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| DrugBank | |
| ECHA InfoCard | 100.127.053 |
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PubChem CID
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| Properties | |
| C16H24O4 | |
| Molar mass | 280.36 g/mol |
| Appearance | White to off-white crystalline powder |
| Melting point | 204 to 205 °C (399 to 401 °F; 477 to 478 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
Brefeldin A is a lactone antiviral produced by Eupenicillium brefeldianum. Brefeldin A inhibits protein transport from the endoplasmic reticulum to the Golgi apparatus indirectly by preventing association of COP-I coat to the Golgi membrane. Brefeldin A was initially isolated with hopes to become an antiviral drug but is now primarily used in research to study protein transport.
The compound gets its name from a species of anamorph fungus of the Penicillium genus known as Eupenicillium brefeldianum, though it is found in a variety of species that span several genera. It was first isolated from Penicillium decumbens in 1958 by V.L. Singleton who initially called it Decumbin. It was later identified as a metabolite by H.P. Siggs who then went on to identify the chemical structure of the compound in 1971. Since then several successful total synthesis methods have been described. Interest in researching brefeldin A was initially lacking due to poor antiviral activity. However, upon discovery of its mechanism involving disruption of protein transport by Takatsuki and Tamura in 1985 and the cytotoxic effects observed in certain cancer cell lines, research efforts were revitalized. It is currently used solely in research mainly as an assay tool for studying membrane traffic and vesicle transport dynamics between the endoplasmic reticulum and Golgi apparatus.
Brefeldin A is found naturally as a white to off-white crystalline solid. It forms a clear colorless solution when dissolved. It is soluble in methanol (10 mg/mL), ethanol (5 mg/mL), DMSO (20 mg/mL), acetone, and ethyl acetate (1 mg/mL) without the aid of heating. It is poorly soluble in water (slightly miscible). It is sold commercially with a purity of 98% or greater. It is recommended that it be stored desiccate at -20 °C away from direct sunlight. Its suggested shelf life for use is 6 months as a solid and 1 month as a solution with tightly sealed storage at -20 °C. Since the compound is combustible, contamination with oxidizing agents should be avoided to prevent the risk of fire. Direct contact should be avoided as well.
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