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F4767

Sigma-Aldrich

Filipin III from Streptomyces filipinensis

≥85% (HPLC)

Synonyma:

Filimarisin

Přihlásitk zobrazení cen stanovených pro organizaci a smluvních cen
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About This Item

Empirický vzorec (Hillův zápis):
C35H58O11
Číslo CAS:
480-49-9
Molekulová hmotnost:
654.83
MDL number:
MFCD00466923
UNSPSC Code:
12352202
PubChem Substance ID:
24894871
NACRES:
NA.77

Quality Level

300

assay

≥85% (HPLC)

form

powder

mp

163-180  °C

solubility

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

antibiotic activity spectrum

fungi
yeast

mode of action

cell membrane | interferes

storage temp.

−20°C

SMILES string

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-

InChI key

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.

Biochem/physiol Actions

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.

Other Notes

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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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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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