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F4767

Sigma-Aldrich

Filipin III from Streptomyces filipinensis

≥85% (HPLC)

Synonym(s):

Filimarisin

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About This Item

Empirical Formula (Hill Notation):
C35H58O11
CAS Number:
480-49-9
Molecular Weight:
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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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