Brefeldin A

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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 YesY
PubChem 5287620
ChemSpider 4449949 YesY
DrugBank DB07348
ChEBI CHEBI:48080 YesY
ChEMBL CHEMBL19980 YesY
Jmol-3D images {{#if:O=C/1O[C@H](CCC/C=C/[C@H]2[C@H]([C@H](O)/C=C\1)C[C@@H](O)C2)C|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
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Brefeldin A is a lactone antibiotic produced by fungal organisms such as Eupenicillium brefeldianum. Brefeldin A inhibits protein transport from the endoplasmic reticulum (ER) to the Golgi apparatus indirectly by preventing formation of COPII-mediated[1] transport vesicles. Brefeldin A was initially isolated as an anti-viral antibiotic[2] but is now primarily used in biological research to study protein transport.

Physical data

Brefeldin A forms a clear colorless solution at 10 mg/ml in both dichloromethane and methanol.[3]

Biological effects

In mammalian and yeast cells, the main target of brefeldin A appears to be a Guanine nucleotide exchange factor called Sar1. Sar1 mediates formation of transport vesicles by recruiting COPII coat proteins to cargo-bound receptor proteins found in the membrane of the rough ER. Inhibition of Sar1 activity prevents the anterograde movement of secretory proteins out of the ER. The accumulation of protein within the ER leads to the collapse of the Golgi stacks, triggers activation of unfolded protein response (UPR) (or ER stress)[4][5] and ultimately causes apoptosis.

References

  1. ↑ http://www.cellsignal.com/pdf/9972.pdf
  2. ↑ 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. 
  3. ↑ Brefeldin A product page from Fermentek
  4. ↑ Pahl HL, Baeuerle (Jun 1995). "A novel signal transduction pathway from the endoplasmic reticulum to the nucleus is mediated by transcription factor NF-kappa B". EMBO J. 14 (11): 2580–8. PMID 7781611. 
  5. ↑ Kober L, Zehe C, Bode J (October 2012). "Development of a novel ER stress based selection system for the isolation of highly productive clones". Biotechnol. Bioeng. 109 (10): 2599–611. doi:10.1002/bit.24527. PMID 22510960. 

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