B5936

Brefeldina A

Name: Brefeldina A
Brand: SIGMA

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

Sinonimo/i:

γAcido ,4-diidrossi-2-(6-idrossi-1-eptenil)-4-ciclopentanecrotonico λ-lattone, Ascotossina, BFA, Cianeina, Decumbina

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Informazioni su questo articolo

Formula empirica (notazione di Hill):

C₁₆H₂₄O₄

Numero CAS:

20350-15-6

Peso molecolare:

280.36

UNSPSC Code:

51102829

NACRES:

NA.85

PubChem Substance ID:

329773270

MDL number:

MFCD12913297

Beilstein/REAXYS Number:

25191

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InChI key

KQNZDYYTLMIZCT-KQPMLPITSA-N

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

biological source

Penicillium brefeldianum

vapor pressure

0.56 hPa ( 20 °C)

form

ready-to-use solution

autoignition temp.

301 °C

concentration

10 mg/mL in DMSO

solubility

DMSO: 10 mg/mL

antibiotic activity spectrum

neoplastics

mode of action

cell membrane | interferes

shipped in

wet ice

storage temp.

2-8°C

Quality Level

200

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Categorie correlate

Chemistry & Biochemicals

Antibiotics

Biochemicals

Cell Culture Supplements & Reagents

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1 of 4

Questo articolo	B6542	B7651	M3536
Sigma-Aldrich B5936 Brefeldin A	Sigma-Aldrich B6542 Brefeldin A	Sigma-Aldrich B7651 Brefeldin A	Sigma-Aldrich M3536 Mycophenolic acid
antibiotic activity spectrum neoplastics	antibiotic activity spectrum neoplastics	antibiotic activity spectrum neoplastics	antibiotic activity spectrum -
mode of action cell membrane \| interferes	mode of action protein synthesis \| interferes	mode of action protein synthesis \| interferes	mode of action enzyme \| inhibits
Quality Level 200	Quality Level 300	Quality Level 300	Quality Level 300
form solution	form powder	form powder	form powder
biological source Penicillium brefeldianum	biological source Penicillium brefeldianum	biological source Penicillium brefeldianum	biological source Penicillium brevicompactum
concentration 10 mg/mL in DMSO	concentration -	concentration -	concentration -

Application

Brefeldin A produced from Penicillium brefeldianum may be used to study protein and lipid transport between Golgi complex and the cell surface.

Biochem/physiol Actions

Altera la struttura e la funzione dell′apparato di Golgi; è un attivatore del ciclo della sfingomielina.

La brefeldina A (BFA) è un metabolita fungino che altera la struttura e la funzione dell′apparato di Golgi. La BFA è un attivatore del ciclo della sfingomielina. In cellule tumorali umane è stata osservata apoptosi mediata dalla brefeldina A.

Brefeldin A (BFA) is a fungal metabolite which disrupts the structure and function of the Golgi apparatus by inhibiting transport of proteins from ER to Golgi and inducing retrograde protein transport from the Golgi apparatus to the endoplasmic reticulum.[1] BFA inhibits the transport of sphingomyelin to the surface of mammalian cells.[2] The ester derivatives of BFA exhibit anti-cancer properties.[3]

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Store under inert gas. Hygroscopic.Storage class (TRGS 510): Combustible liquids

Classe di stoccaggio

10 - Combustible liquids

flash_point_f

188.6 °F - closed cup

flash_point_c

87 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, multi-purpose combination respirator cartridge (US)

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Transport of sphingomyelin to the cell surface is inhibited by brefeldin A and in mitosis, where C6-NBD-sphingomyelin is translocated across the plasma membrane by a multidrug transporter activity.

A van Helvoort et al.

Journal of cell science, 110 ( Pt 1), 75-83 (1997-01-01)

Sphingomyelin is a major lipid of the mammalian cell surface. The view that sphingomyelin, after synthesis in the Golgi lumen, reaches the outer leaflet of the plasma membrane on the inside of carrier vesicles has been challenged by inconsistencies in

Antiviral activity of brefeldin A and verrucarin A.

G Tamura et al.

The Journal of antibiotics, 21(2), 160-161 (1968-02-01)

Parallel T-cell cloning and deep sequencing of human MAIT cells reveal stable oligoclonal TCRβ repertoire.

Marco Lepore et al.

Nature communications, 5, 3866-3866 (2014-05-17)

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

Synthesis and anticancer activity of brefeldin A ester derivatives.

Nwanne O Anadu et al.

Journal of medicinal chemistry, 49(13), 3897-3905 (2006-06-23)

Ester derivatives of brefeldin A (BFA) were synthesized to determine which of its two hydroxyl groups could be modified while still maintaining biological activity. The compounds were tested for antiproliferative activity in the National Cancer Institute's 60 cancer cell line

A CREB3-ARF4 signalling pathway mediates the response to Golgi stress and susceptibility to pathogens.

Jan H Reiling et al.

Nature cell biology, 15(12), 1473-1485 (2013-11-05)

Treatment of cells with brefeldin A (BFA) blocks secretory vesicle transport and causes a collapse of the Golgi apparatus. To gain more insight into the cellular mechanisms mediating BFA toxicity, we conducted a genome-wide haploid genetic screen that led to

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