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B7651

Sigma-Aldrich

Brefeldin A

from Penicillium brefeldianum, ≥99% (HPLC and TLC)

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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:
Molecular Weight:
280.36
Beilstein:
25191
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

Penicillium brefeldianum

Quality Level

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

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1 of 4

This Item
B6542B3061B5936
Brefeldin A from Penicillium brefeldianum, ≥99% (HPLC and TLC)

B7651

Brefeldin A

Brefeldin A ≥99% (HPLC and TLC), BioXtra, for molecular biology

B6542

Brefeldin A

Borrelidin from Streptomyces parvulus, ≥98% (HPLC)

B3061

Borrelidin

Brefeldin A from Penicillium brefeldianum, Ready Made Solution, 10 mg/mL in DMSO

B5936

Brefeldin A

assay

≥99% (HPLC and TLC)

assay

≥99% (HPLC and TLC)

assay

≥98% (HPLC)

assay

-

Quality Level

300

Quality Level

300

Quality Level

200

Quality Level

200

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

solubility

DMSO: 10 mg/mL

solubility

DMSO: 10 mg/mL (Store stock solutions at -20 °C)

solubility

DMSO: 1 mg/mL, methanol: 1 mg/mL

solubility

DMSO: 10 mg/mL

biological source

Penicillium brefeldianum

biological source

Penicillium brefeldianum

biological source

Streptomyces parvulus

biological source

Penicillium brefeldianum

General description

Chemical structure: macrolide

Application

Brefeldin A has been shown to increase CRISPR genome editing efficiency. To see other small molecule CRISPR enhancers, visit sigma.com/CRISPR-enhancers.

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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Kensuke Shibata et al.
Blood, 118(3), 586-593 (2011-05-25)
Unlike conventional T cells, which are exported from the thymus as naive cells and acquire effector functions upon antigen encounter in the periphery, a subset of γδ T cells differentiates into effectors that produce IL-17 within the fetal thymus. We
Vyoma K Patel et al.
Atherosclerosis, 263, 15-23 (2017-06-02)
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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)
Antonio Riva et al.
Frontiers in physiology, 12, 632502-632502 (2021-03-30)
Immunoregulatory checkpoint receptors (CR) contribute to the profound immunoparesis observed in alcohol-related liver disease (ALD) and in vitro neutralization of inhibitory-CRs TIM3/PD1 on anti-bacterial T-cells can rescue innate and adaptive anti-bacterial immunity. Recently described soluble-CR forms can modulate immunity in
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Mucosal-associated invariant T (MAIT) cells are abundant in humans and recognize conserved bacterial antigens derived from riboflavin precursors, presented by the non-polymorphic MHC class I-like molecule MR1. Here we show that human MAIT cells are remarkably oligoclonal in both the

Articles

Modulation of homology-directed repair (HDR) within the context of CRISPR-genome editing has led to the identification of small molecules that enhance CRISPR-mediated HDR efficiency in various cell types.

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