As provided, every batch of this product released has been tested for solubility in methanol at concentrations up to about 10 mg/mL. It is also known to be soluble in organic solvents, e.g., ethanol (2 mg/mL), DMSO (5 mg/mL), and dimethyl formamide (10 mg/mL). The optimal solvent may vary depending on the specific application.
F4767
Filipin III from Streptomyces filipinensis
≥85% (HPLC)
Synonym(s):
Filimarisin
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All Photos(4)
About This Item
Empirical Formula (Hill Notation):
C35H58O11
CAS Number:
Molecular Weight:
654.83
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.
Recommended Products
Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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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
[Assembly of actin filaments induced by sequestration of membrane cholesterol in transformed cells].
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.
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
Christophe Stenger et al.
Journal of neurochemistry, 123(4), 467-476 (2012-08-23)
Brain lipid homeostasis is important for maintenance of brain cell function and synaptic communications, and is intimately linked to age-related cognitive decline. Because of the blood-brain barrier's limiting nature, this tissue relies on a complex system for the synthesis and
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Good afternoon; I would be very grateful if you could clarify me which is the best solvent for filipin III (F4767) stock solution preparation. Product specification is different from product information (methanol; ethanol; DMSO..). Thank you in advance.
1 answer-
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