B7651

Brefeldin A

from Penicillium brefeldianum, ≥99% (HPLC and TLC), powder, activator of the sphingomyelin cycle

• Synonym(s): Nectrolide, γ,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone, Ascotoxin, BFA, Cyanein, Decumbin
• Empirical Formula (Hill Notation): C₁₆H₂₄O₄
• CAS Number: 20350-15-6
• Molecular Weight: 280.36
• Beilstein/REAXYS Number: 25191
• MDL number: MFCD12913297
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278285
• NACRES: NA.77

Properties

• Product Name: Brefeldin A, from Penicillium brefeldianum, ≥99% (HPLC and TLC)
• biological source: Penicillium brefeldianum
• Quality Level: 300
• assay: ≥99% (HPLC and TLC)
• form: powder
• solubility: DMSO: 10 mg/mL
• antibiotic activity spectrum: neoplastics
• 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

Description

General description

Brefeldin A (BFA) is a fungal metabolite containing a 13-membered macrocyclic lactone ring. It inhibits protein and nucleic acid synthesis. BFA blocks the exchange of GDP for GTP on adenosine ribosylation factors (ARFs), thereby hindering the binding of coat protein (β-COP) and consequently 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. Brefeldin A has been shown to increase CRISPR-mediated homology-directed repair (HDR) efficiency. It demonstrates a diverse array of biological functions, including antitumor, antiviral, antibiotic, antimitotic, antifungal and antinematodal properties.

Application

Brefeldin A has been used to:

• increase CRISPR genome editing efficiency.
• facilitate the measurement of cytokine production
• block intracellular transports in cell culture experiments

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.

Brefeldin A has been shown to increase CRISPR-mediated homology-directed repair (HDR) efficiency.

Disrupts the structure and function of the Golgi apparatus; activator of the sphingomyelin cycle.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: P301 + P310
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves