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B5936

Sigma-Aldrich

Brefeldin A

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C16H24O4
CAS Number:
20350-15-6
Molecular Weight:
280.36
Beilstein:
25191
MDL number:
MFCD12913297
UNSPSC Code:
51102829
PubChem Substance ID:
329773270
NACRES:
NA.85
Pricing and availability is not currently available.

biological source

Penicillium brefeldianum

Quality Level

200

vapor pressure

0.56 hPa ( 20 °C)

form

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

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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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

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

Other Notes

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

188.6 °F - closed cup

Flash Point(C)

87 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000221236
0000201440
0000221236
0000201440
0000406499

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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)
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
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
Laura Jeanbart et al.
Cancer immunology research, 2(5), 436-447 (2014-05-06)
The sentinel or tumor-draining lymph node (tdLN) serves as a metastatic niche for many solid tumors and is altered via tumor-derived factors that support tumor progression and metastasis. tdLNs are often removed surgically, and therapeutic vaccines against tumor antigens are
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Questions

1–3 of 3 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. How stable is the solution if kept at 4 ºC? thanks

    1 answer

    1. This product is a 10 mg/mL solution in DMSO. The recommended storage temperature is 2-8°C. Assuming proper handling and storage, the item will be stable until the recommended retest date reported on the lot specific Certificate of Analysis. The product is assigned a retest date of 2 years from the date of Quality Release.

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