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Merck

F4767

Sigma-Aldrich

Filipin III from Streptomyces filipinensis

≥85% (HPLC)

Sinónimos:

Filimarisin

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About This Item

Fórmula empírica (notación de Hill):
C35H58O11
Número de CAS:
Peso molecular:
654.83
Número MDL:
Código UNSPSC:
12352202
ID de la sustancia en PubChem:
NACRES:
NA.77

Nivel de calidad

Ensayo

≥85% (HPLC)

Formulario

powder

mp

163-180  °C

solubilidad

methanol: 9.80-10.20 mg/mL, clear, colorless to yellow

espectro de actividad antibiótica

fungi
yeast

Modo de acción

cell membrane | interferes

temp. de almacenamiento

−20°C

cadena SMILES

CCCCCC(O)C1C(O)CC(O)CC(O)CC(O)CC(O)CC(O)CC(O)C(C)=C\C=C\C=C\C=C\C=C\C(O)C(C)OC1=O

InChI

1S/C35H58O11/c1-4-5-11-16-31(42)34-33(44)22-29(40)20-27(38)18-25(36)17-26(37)19-28(39)21-32(43)23(2)14-12-9-7-6-8-10-13-15-30(41)24(3)46-35(34)45/h6-10,12-15,24-34,36-44H,4-5,11,16-22H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,23-14-

Clave InChI

IMQSIXYSKPIGPD-BWJOQPJXSA-N

Aplicación

Filipin has been used in a double staining procedure as a probe for the detection of lipoproteins in polyacrylamide gel and immobilized on nitrocellulose membranes.
Filipin has been used in a double staining procedure as a probe for the detection of lipoproteins in polyacrylamide gel and immobilized on nitrocellulose membranes. It is also widely used to localize and quantitate unesterified cholesterol by virtue of a specific fluorescent complex.

Acciones bioquímicas o fisiológicas

Filipin is a polyene macrolide antibiotic and antifungal. The antifungal mechanism of action may be due to altering membrane permeability and associated functions by binding to membrane sterols. Filipin inhibits prion protein (PrP) endocytosis and causes the release of PrP from the plasma membrane.

Otras notas

Filipin III is the major component of 8 isomeric components in filipin.

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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Kari Fine-Coulson et al.
PloS one, 7(9), e45028-e45028 (2012-10-02)
Dynamic, cholesterol-dense regions of the plasma membrane, known as lipid rafts (LR), have been observed to develop during and may be directly involved in infection of host cells by various pathogens. This study focuses on LR aggregation induced in alveolar
Henrik Tjellström et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 24(4), 1128-1138 (2009-12-08)
As in other eukaryotes, plant plasma membranes contain sphingolipids, phospholipids, and free sterols. In addition, plant plasma membranes also contain sterol derivatives and usually <5 mol% of a galactolipid, digalactosyldiacylglycerol (DGDG). We earlier reported that compared to fully fertilized oats
Patrycja Kozik et al.
Nature cell biology, 15(1), 50-60 (2012-12-25)
Clathrin-mediated endocytosis is essential for a wide range of cellular functions. We used a multi-step siRNA-based screening strategy to identify regulators of the first step in clathrin-mediated endocytosis, formation of clathrin-coated vesicles (CCVs) at the plasma membrane. A primary genome-wide
Dimitri Moreau et al.
EMBO reports, 20(7), e47055-e47055 (2019-07-04)
Most cells acquire cholesterol by endocytosis of circulating low-density lipoproteins (LDLs). After cholesteryl ester de-esterification in endosomes, free cholesterol is redistributed to intracellular membranes via unclear mechanisms. Our previous work suggested that the unconventional phospholipid lysobisphosphatidic acid (LBPA) may play
T N Efremova et al.
Tsitologiia, 54(6), 508-514 (2012-09-25)
Cholesterol is one of the major lipid components of plasma membrane and it plays an important role in various signaling processes in mammalian cells. Our study focused on the role of membrane cholesterol in organization and dynamics of actin cytoskeleton.

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