Brefeldin A Chemical Properties

Melting point:

200-205 °C

alpha 

93 º (C=2 IN MEOH)

Boiling point:

492.7±45.0 °C(Predicted)

Density 

1.108±0.06 g/cm3(Predicted)

vapor pressure 

0.56 hPa ( 20 °C)

Flash point:

87 °C

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

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

form 

Crystalline Powder

pka

12.92±0.60(Predicted)

color 

White to almost white

Water Solubility 

Soluble in dimethylsulfoxide, dichloromethane and ethanol. Slightly soluble in water.

Merck 

13,1355

BRN 

25191

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.

InChIKey

QSECOIOBNZLGOD-OBCVZTHZSA-N

CAS DataBase Reference

20350-15-6

Safety Information

Hazard Codes 

Xn,T

Risk Statements 

22-25-36/37/38-20/21/22

Safety Statements 

24/25-45-36-26

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

GY8410000

Autoignition Temperature

301 °C

HS Code 

29411090

Toxicity

LD50 i.p. in mice: >200 mg/kg (Haerri)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Brefeldin A Usage And Synthesis

Description

Brefeldin A (20350-15-6) is a specific inhibitor of protein translocation from endoplasmic reticulum to Golgi. Induces apoptosis. Brefeldin A activates sphingomyelin metabolism. Cell permeable.

Chemical Properties

White Powder

Uses

A macrolide isolated from Penicillium brefeldianum. It affects the vesticular transport of the Golgi apparatus and induces DNA fragmentation which leads to apoptosis

Uses

Brefeldin A is a potent inhibitor of cell growth first described in 1958, then independently rediscovered by several groups as a potent active in a broad range of bioassays. Brefeldin has antiviral, antibiotic, antifungal, antitumour and herbicidal activity. Early studies on the mode of action of brefeldin identified inhibition of protein and nucleic acid synthesis by disruption of the Golgi apparatus. The precise molecular target is a subset of Sec7-type GTP exchange factors (GEFs) that activate a small GTPase, Arf1p, an integral component of protein trafficking and signalling.

Uses

Brefeldin A (BFA) is a natural fungal metabolite which has been used extensively to study intracellular transport by vesicles or endosomes. Early studies demonstrated that BFA reversibly interferes with protein trafficking and secretion mediated by the Golgi apparatus and endoplasmic reticulum. BFA directly and reversibly inhibits Sec7 domain-containing guanine-exchange factors which are necessary for ADP-ribosylation factor activation associated with vesicular transport (IC50 = ~10 μM). BFA is used to study endosomal trafficking and function in cells of plants as well as those of fungi, invertebrates, and vertebrates.

Definition

ChEBI: A metabolite from Penicillium brefeldianum that exhibits a wide range of antibiotic activity.

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. Blocks binding of ADP-ribosylation factor to the Golgi and inhibits the GDP-GTP exchange. Inhibits the activity of BIG1 and BIG2, the guanine-nucleotide exchange proteins for ADP-ribosylation factors. Also available as a 25 mM solution in DMSO (Cat. No. 500583).

Biological Activity

Reversible inhibitor of protein translocation from the endoplasmic reticulum (ER) to the Golgi apparatus. Blocks binding of ADP-ribosylation factor to the Golgi apparatus and inhibits GDP-GTP exchange.

Biochem/physiol Actions

Primary TargetBlocks translocation of proteins from the endoplasmic reticulum (ER) to the Golgi apparatus

storage

-20°C (desiccate)

Purification Methods

Brefeldin A was isolated from Penicillium brefeldianum and recrystallised from aqueous MeOH/EtOAc or MeOH. Its solubility in H2O is 0.6mg/mL, 10mg/mL in MeOH and 24.9mg/mL in EtOH. The O-acetate recrystallises from Et2O/pentane and has m 130-131o, [] D +17o (c 0.95, MeOH). [Sigg Helv Chim Acta 47 1401 1964, UV and IR: H.rri et al. Helv Chim Acta 46 1235 1963, total synthesis: Kitahara et al. Tetrahedron 3021 1979, X-ray : Weber et al. Helv Chim Acta 54 2763 1971, Beilstein 18 III/IV 1220.]

References

1) Fujiwara et al. (1988) Brefeldin A causes disassembly of the Golgi complex and accumulation of secretory proteins in the endoplasmic reticulum; J. Biol. Chem., 263 18545 2) Shao et al. (1996), Brefeldin A is a potent inducer of apoptosis in human cancer cells independently of p53; Exp. Cell Res., 227 190 3) Linardic et al. (1996), Brefeldin A promotes hydrolysis of sphingomyelin; Cell Growth Differ., 7 765

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