CAS 20350-15-6|Brefeldin A
| Common Name | Brefeldin A | ||
|---|---|---|---|
| CAS Number | 20350-15-6 | Molecular Weight | 280.359 |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 492.7±45.0 °C at 760 mmHg |
| Molecular Formula | C16H24O4 | Melting Point | 200-205ºC |
| MSDS | ChineseUSA | Flash Point | 180.8±22.2 °C |
| Symbol | GHS06 | Signal Word | Danger |
Names
| Name | brefeldin A |
|---|---|
| Synonym | More Synonyms |
Brefeldin A BiologicalActivity
| 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 >>AutophagySignaling Pathways >>Cell Cycle/DNA Damage >>CRISPR/Cas9Signaling Pathways >>Autophagy >>MitophagyNatural Products >>OthersResearch 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. |
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 |
| InChIKey | KQNZDYYTLMIZCT-AQXDOAQYSA-N |
| SMILES | CC1CCCC=CC2CC(O)CC2C(O)C=CC(=O)O1 |
| Storage condition | 2~8°C |
Toxicological Information
CHEMICAL IDENTIFICATION |
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
- 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 |
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Synonyms
| 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 |
