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Filipin III Catalog No.GC12048

Fluorescing antibiotic used for the detection of lipoproteins

Size Price Stock Qty
500ug
$110.00
In stock
1mg
$153.00
In stock
5mg
$613.00
In stock

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Sample solution is provided at 25 µL, 10mM.

Quality Control

Quality Control & SDS

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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.

Chemical Properties

Cas No. 480-49-9 SDF
Synonyms N/A
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
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
Formula C35H58O11 M.Wt 654.83
Solubility 2mg/ml in ethanol; 5mg/ml in DMSO; 10mg/ml in DMF Storage Store at -20°C
General tips For 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.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request
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Background

Cholesterol is both an important structural component of cell membranes and an early intermediate in hormone and bile acid biosynthesis. The localization and measurement of cholesterol in cells is therefore of great interest. 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]

Reference:
[1]. Castanho, M.A., Coutinho, A., and Prieto, M.J. Absorption and fluorescence spectra of polyene antibiotics in the presence of cholesterol J. Biol. Chem. 267(1), 204-209 (1992).
[2]. Miller, R.G. Mini Review. The use and abuse of filipin to localize cholesterol in membranes Cell Biol. Int. Rep. 8(7), 519-535 (1984).
[3]. Severs, N.J., and Robenek, H. Detection of microdomains in biomembranes. An appraisal of recent developments in freeze-fracture cytochemistry Biochimica et Biophysica Acta 737, 373-408 (1983)