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Filipin III

Catalog No.
B6034
cholesterol-binding, fluorescing antibiotic used for the detection of lipoproteins
Grouped product items
SizePriceStock Qty
500ug
$118.00
Ship with 5-10 days
1mg
$164.00
Ship with 5-10 days
5mg
$655.00
Ship with 5-10 days

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Email: [email protected]

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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.

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

Chemical Properties

Physical AppearanceA crystalline solid
StorageStore at -20°C
M.Wt654.83
Cas No.480-49-9
FormulaC35H58O11
SolubilitySoluble 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
SDFDownload SDF
Canonical SMILESO[[email protected]@H]1/C(C)=C/C=C/C=C/C=C/C=C/[[email protected]](O)[[email protected]@H](C)OC([[email protected]@]([[email protected]](O)CCCCC)([H])[[email protected]@H](O)C[[email protected]@H](O)C[[email protected]@H](O)C[[email protected]@H](O)C[[email protected]@H](O)C[[email protected]@H](O)C1)=O
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

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 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.

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.

Quality Control

Quality Control & MSDS

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Chemical structure

Filipin III

Related Biological Data

Filipin III

Related Biological Data

Filipin III