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F4767

Sigma-Aldrich

Filipin III from Streptomyces filipinensis

≥85% (HPLC)

Synonyme(s) :

Filimarisin

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About This Item

Formule empirique (notation de Hill):
C35H58O11
Numéro CAS:
480-49-9
Poids moléculaire :
654.83
Numéro MDL:
MFCD00466923
Code UNSPSC :
12352202
ID de substance PubChem :
24894871
Nomenclature NACRES :
NA.77

Niveau de qualité

300

Pureté

≥85% (HPLC)

Forme

powder

Pf

163-180  °C

Solubilité

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

Spectre d'activité de l'antibiotique

fungi
yeast

Mode d’action

cell membrane | interferes

Température de stockage

−20°C

Chaîne 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-

Clé InChI

IMQSIXYSKPIGPD-BWJOQPJXSA-N

Application

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.

Actions biochimiques/physiologiques

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.

Autres remarques

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

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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.
Laura Calpe-Berdiel et al.
Atherosclerosis, 223(2), 332-341 (2012-07-04)
The ABCA2 transporter shares high structural homology to ABCA1, which is crucial for the removal of excess cholesterol from macrophages and, by extension, in atherosclerosis. It has been suggested that ABCA2 sequesters cholesterol inside the lysosomes, however, little is known
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