CAS Number20350-15-6
Synonymsg,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic Acid l-Lactone; Brefeldin; Synergisidin; Brefeldin A; cyanein; Cyanaein; Brefeldin-A; MFCD00083258; ASCOTOXIN; decumbin; BFA; Nectrolide; (+)-Brefeldin A
Molecular FormulaC16H24O4
Molecular Weight280.36
Purity98.00%
Density1.1±0.1 g/cm3
Boiling Point492.7±45.0 °C at 760 mmHg
Melting Point200-205ºC
Appearanceready-to-use solution
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 20350-15-6 |
| Catalog No. | 2A-9038385 |
| Chinese Name | 布雷菲德菌素A |
| Synonyms | g,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic Acid l-Lactone; Brefeldin; Synergisidin; Brefeldin A; cyanein; Cyanaein; Brefeldin-A; MFCD00083258; ASCOTOXIN; decumbin; BFA; Nectrolide; (+)-Brefeldin A |
| Molecular Formula | C16H24O4 |
| Molecular Weight | 280.36 |
| Purity | 98.00 |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 492.7±45.0 °C at 760 mmHg |
| Melting Point | 200-205ºC |
| Appearance | ready-to-use solution |
| Storage Condition | 2-8℃ |
| Application | Brefeldin A is a specific inhibitor of protein trafficking, which blocks protein transport from the endoplasmic reticulum to the Golgi complex. |
| HTC | 29411090 |
| PubChem ID | 329773270 |
| MDL Number | MFCD12913297 |
| SMILES | 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 |
| Beilstein/REAXYS | 25191 |
| NACRES Code | NA.85 |
| UNSPSC | 51102829 |
| Hazard Symbols | 6.1 |
| MSDS | msds/38385_1_20350_15_6.pdf |
| Bioactivity | 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. 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 |
| Use of | Brefeldin A is a specific inhibitor of protein trafficking which blocks the protein transport from the endoplasmic reticulum to the Golgi complex. Properties Articles869 Name brefeldin A Synonym More Synonyms 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 CRISPR/Cas9 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. [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 Molecular Formula C16H24O4 Exact Mass 280.167450 PSA 66.76000 Index of Refraction 1.513 InChIKey KQNZDYYTLMIZCT-AQXDOAQYSA-N |
| Transport Info | Product Name: Brefeldin A |
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