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B7651

Brefeldin A

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

동의어(들):

Nectrolide, γ,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone, Ascotoxin, BFA, Cyanein, Decumbin

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제품정보 (DICE 배송 시 비용 별도)

실험식(Hill 표기법):
C16H24O4
CAS 번호:
20350-15-6
Molecular Weight:
280.36
NACRES:
NA.77
PubChem Substance ID:
24278285
UNSPSC Code:
12352200
MDL number:
MFCD12913297
Beilstein/REAXYS Number:
25191
Assay:
≥99% (HPLC and TLC)
Form:
powder
Quality level:
300
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제품 이름

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

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.

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pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

저장 등급

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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시험 성적서(COA)

Lot/Batch Number
0000545128
0000545128
0000438981
0000438981
0000438974

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Concise Total Syntheses of (+)-Brefeldin A, Diastereomers and Analogs and Their Biological Activity
Dr. Mikhail K. Klychnikov et.al.,
Chemistry?A European Journal , 1 (2023)
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