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Filipin III

Filipin III

Catalog No.

B6034

cholesterol-binding, fluorescing antibiotic used for the detection of lipoproteins

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Grouped product items
Size	Price	Stock
500ug	$165.00	Ship with 5-10 days
1mg	$230.00	Ship with 5-10 days
5mg	$917.00	Ship with 5-10 days

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Background
Product Citation
Chemical Properties
Protocol
Quality Control

Background

Filipin is the collective name given to four isomeric polyene macrolides isolated from cultures of S. filipinensis; Filipin III is the predominant isomer and the one used in most studies. Filipin binds to cholesterol in membranes, forming ultrastructural aggregates and complexes which can be visualized by freeze-fracture electron microscopy [1,2]. The binding of cholesterol also decreases the intrinsic fluorescence of Filipin, and this property has also been used to detect cholesterol in membrane fractions [3].

References:

[1]. Castanho M A R B, Coutinho A, Prieto M J E. Absorption and Fluorescence Spectra of Polyene Antibiotics in the Presence of Cholesterol. Journal of Biological Chemistry, 1992, 267(1): 204-209.

[2]. MILLER, R. The use and abuse of filipin to localize cholesterol in membranes. Cell Biology International Reports, 1984, 8(7): 519-535.

[3]. Nicholas J. Severs, Horst Robenek. Detection of microdomains in biomembranes An appraisal of recent developments in freeze-fracture cytochemistry. Biochim Biophys Acta, 1983,737(3-4):373-408.

Product Citation

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Chemical Properties

Physical Appearance	A crystalline solid
Storage	Store at -20°C, protect from light. This product is unstable in solution. It is recommended to avoid light and store it separately to avoid repeated freeze-thaw cycles. Use it as soon as possible
M.Wt	654.83
Cas No.	480-49-9
Formula	C₃₅H₅₈O₁₁
Solubility	Soluble in DMSO
Chemical Name	(3R,4S,6S,8S,10R,12R,14R,16S,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,16,27-octahydroxy-3-((R)-1-hydroxyhexyl)-17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one
SDF	Download SDF
Canonical SMILES	O[C@@H]1/C(C)=C/C=C/C=C/C=C/C=C/[C@H](O)[C@@H](C)OC([C@@]([C@H](O)CCCCC)([H])[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C1)=O
Shipping Condition	Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips	We do not recommend long-term storage for the solution, please use it up soon.

Protocol

Cell experiment [1]:
Cell lines	ergosterol-containing ciliary membranes
Preparation method	This compound is soluble in DMSO. General tips for obtaining a higher concentration: Please warm the tube at 37°C for 10 minutes and/or shake it in the ultrasonic bath for a while.
Reacting condition	12.7 μM
Applications	Filipin induced lysis of lecithin-cholesterol and lecithin-ergosterol vesicles, but did not lyse vesicles prepared from lecithin alone and from mixtures of lecithin and epicholesterol, thiocholesterol, androstan-3/3-ol, or cholestanol. Filipin treatment of ergosterol-containing ciliary membranes produced annuli with mean diameter almost identical with that in filipin-treated lecithin-ergosterol vesicles.
Other notes	Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.
References: [1]. Bittman R, Chen W C, Anderson O R. Interaction of filipin III and amphotericin B with lecithin-sterol vesicles and cellular membranes. Spectral and electron microscope studies[J]. Biochemistry, 1974, 13(7): 1364-1373.