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15870

Brefeldin A

≥99.0% (TLC), from Penicillium brefeldianum

Synonym(s):

γ,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone, Ascotoxin, BFA, Cyanein, Decumbin

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About This Item

Empirical Formula (Hill Notation):
C16H24O4
CAS Number:
20350-15-6
Molecular Weight:
280.36
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
25191
MDL number:
MFCD12913297
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biological source

Penicillium brefeldianum

assay

≥99.0% (TLC)

mp

200-205 °C

solubility

methanol: 10 mg/mL, clear, colorless to faintly yellow

mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

C[C@H]1CCC\C=C\[C@@H]2C[C@H](O)C[C@H]2[C@H](O)\C=C\C(=O)O1

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-KQPMLPITSA-N

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General description

Chemical structure: macrolide

Biochem/physiol Actions

Brefeldin A (BFA) is a fungal metabolite which disrupts the structure and function of the Golgi apparatus. BFA is an activator of the sphingomyelin cycle. Brefeldin A-mediated apoptosis has been observed in human tumor cells.
Disrupts the structure and function of the Golgi apparatus; activator of the sphingomyelin cycle.

Other Notes

Effects a rapid increase of Golgi cisternae volume and subsequent loss of recognizable Golgi apparatus in treated cells.

Regulatory Information

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T Fujiwara et al.
The Journal of biological chemistry, 263(34), 18545-18552 (1988-12-05)
The antiviral antibiotic brefeldin A (BFA) strongly inhibits the protein secretion in cultured rat hepatocytes (Misumi, Y., Misumi, Y., Miki, K., Takatsuki, A., Tamura, G., and Ikehara, Y. (1986) J. Biol. Chem. 261, 11398-11403). We have further examined the inhibitory
Maria Vono et al.
Cell reports, 28(7), 1773-1784 (2019-08-15)
Maternal antibodies (MatAbs) protect offspring from infections but limit their responses to vaccination. The mechanisms of this inhibition are still debated. Using murine early-life immunization models mimicking the condition prevailing in humans, we observed the induction of CD4-T, T follicular helper
J Lippincott-Schwartz et al.
The Journal of cell biology, 112(4), 567-577 (1991-02-01)
Brefeldin A (BFA) causes rapid redistribution of Golgi proteins into the ER, leaving no definable Golgi apparatus, and blocks transport of proteins into post-Golgi compartments in the cell. In this study we follow the disassembly of the Golgi apparatus in
John A Zaia et al.
Biology of blood and marrow transplantation : journal of the American Society for Blood and Marrow Transplantation, 15(3), 315-325 (2009-02-11)
It has been shown that activating killer Ig-like receptor (aKIR) genes are important for control of cytomegalovirus (CMV) reactivation after hematopoietic cell transplantation (HCT). To date, using the broad classification of KIR haplotypes A and B, the precise role of
Wing-Pui Kong et al.
Journal of virology, 83(5), 2201-2215 (2008-12-26)
An effective AIDS vaccine must control highly diverse circulating strains of human immunodeficiency virus type 1 (HIV-1). Among HIV-1 gene products, the envelope (Env) protein contains variable as well as conserved regions. In this report, an informatic approach to the
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Global Trade Item Number

SKUGTIN
335002-1G04061826738740

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