Brefeldin A

Names

[ CAS No. ]:
20350-15-6

[ Name ]:
Brefeldin A

[Synonym ]:
4H-Cyclopent[f]oxacyclotridecin-4-one, 1,6,7,8,9,11a,12,13,14,14a-decahydro-1,13-dihydroxy-6-methyl-, (1R,2E,6S,10E,11aS,13S,14aR)-
g,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic Acid l-Lactone
Brefeldin
Synergisidin
Brefeldin A
(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
cyanein
1,6,7,8,9,11ab,12,13,14,14aa-Decahydro-1b,13a-dihydroxy-6b-methyl-4H-cyclopent(f)oxacyclotridecin-4-one
Cyanaein
Brefeldin-A
MFCD00083258
ASCOTOXIN
decumbin
BFA
Nectrolide
(+)-Brefeldin A

Biological Activity

[Description]:

Brefeldin A is a specific inhibitor of protein trafficking which blocks the protein transport from the endoplasmic reticulum to the Golgi complex.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Cell Cycle/DNA Damage >> CRISPR/Cas9

Signaling Pathways >> Autophagy >> Mitophagy

Natural Products >> Others

Research Areas >> Cancer

[Target]

CRISPR/Cas9

[In Vitro]

Brefeldin A treatment for 15 h or 40 h, causes dramatic swelling of the Endoplasmic Reticulum (ER) and shifts its localization to the periphery of normal rat kidney (NRK) cells. Prolonged Brefeldin A treatment results in marked disruption of the MT and actin cytoskeleton[1]. ADP-ribosylation of BARS is mediated by formation of a conjugate between Brefeldin A and ADPR. BARS shows BAC binding when incubated with the medium from the BFA-treated CD38+ HeLa cells[2]. Brefeldin A induces anchorage-independent cell death in MDA-MB-231 breast cancer cells, inhibits the formation of MDA-MB-231 colonies in 3D and 2D cultures and inhibits the migration and MMP 9 (Matrix Metallopeptidase 9) activity of MDA-MB-231[3].

[Cell Assay]

Cells are grown on glass coverslips, fixed in 3 % paraformaldehyde in PBS (10 min at room temperature) and then washed in PBS. Cells are permeabilized with 0.01 % Triton X-lOO in PBS at room temperature for 7 min. The coverslips are washed (3 times in PBS/0.2 % Tween) incubated in PBS/O.4 % fish skin gelatin/0.2 % Tween (5 min) and in PBS/2.5 % goat serum/0.2 % Tween (5 min.). After blocking, the cells are incubated with primary antibodies for 45 min at 37°C, and then washed with PBS/0.2 % Tween (5 times, 5 min each). The secondary antibodies are added for 30 min at 37°C and then cells are washed as above. Coverslips are mounted on slides in 9: 1 glycerol/PBS with 0.1 % o-phenylenediamine.

[References]

[1]. Alvarez C, et al. Brefeldin A (BFA) disrupts the organization of the microtubule and the actin cytoskeletons. Eur J Cell Biol. 1999 Jan;78(1):1-14.

[2]. Colanzi A, et al. Molecular mechanism and functional role of brefeldin A-mediated ADP-ribosylation of CtBP1/BARS. Proc Natl Acad Sci U S A. 2013 Jun 11;110(24):9794-9.

[3]. Tseng CN, et al. Brefeldin A reduces anchorage-independent survival, cancer stem cell potential and migration of MDA-MB-231 human breast cancer cells. Molecules. 2014 Oct 29;19(11):17464-77.

[4]. Wang J, et al. Erythroleukemia cells acquire an alternative mitophagy capability. Sci Rep. 2016 Apr 19;6:24641.

[5]. Yu C, et al. Small molecules enhance CRISPR genome editing in pluripotent stem cells. Cell Stem Cell. 2015 Feb 5;16(2):142-7.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
492.7±45.0 °C at 760 mmHg

[ Melting Point ]:
200-205ºC

[ Molecular Formula ]:
C₁₆H₂₄O₄

[ Molecular Weight ]:
280.359

[ Flash Point ]:
180.8±22.2 °C

[ Exact Mass ]:
280.167450

[ PSA ]:
66.76000

[ LogP ]:
1.61

[ Vapour Pressure ]:
0.0±2.8 mmHg at 25°C

[ Index of Refraction ]:
1.513

[ Storage condition ]:
2~8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GY8410000

CHEMICAL NAME :: 4H-Cyclopent(f)oxacyclotridecin-4-one, 1,6,7,8,9,11a-beta,12,13,14,14a-alpha-decahydro-1- beta-13-alpha-dihydroxy-6-beta-methyl-

CAS REGISTRY NUMBER :: 20350-15-6

LAST UPDATED :: 199412

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C16-H24-O4

MOLECULAR WEIGHT :: 280.40

WISWESSER LINE NOTATION :: T5-13- IVO GU OUTJ CQ FQ K1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - mouse Cells - not otherwise specified

DOSE/DURATION :: 200 ug/L

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 39,1148,1986

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)

[ Hazard Codes ]:
Xn: Harmful;T: Toxic;

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
24/25-45-36-26

[ RIDADR ]:
UN 2811 6

[ WGK Germany ]:
3

[ RTECS ]:
GY8410000

[ Hazard Class ]:
6.1

[ HS Code ]:
29411090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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