Filipin III
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.
- 1. Po Hu, Hui Li, et al. "Cholesterol-associated lysosomal disorder triggers cell death of hematological malignancy: Dynamic analysis on cytotoxic effects of LW-218." Acta Pharm Sin B. 2021 Oct;11(10):3178-3192. PMID: 34729308
- 2. Jing Wang, Xiangjin Zhuang, et al. "Cdc42 functions as a regulatory node for tumour‐derived microvesicle biogenesis." J Extracell Vesicles. 2021 Jan;10(3):e12051. PMID: 33473262
- 3. Xue-Ming Zhu , Lin Li, et al. "A VASt-domain protein regulates autophagy, membrane tension, and sterol homeostasis in rice blast fungus." Autophagy. 2020 Nov 11. PMID: 33176558
- 4. Zheng ZG, Zhu ST, et al. "Discovery of a potent SCAP degrader that ameliorates HFD-induced obesity, hyperlipidemia and insulin resistance via an autophagy-independent lysosomal pathway." Autophagy. 2020;1-22. PMID: 32432943
- 5. Dong Y, Gao J, et al. "Antigen-Conjugated Silica Solid Sphere as Nanovaccine for Cancer Immunotherapy." Int J Nanomedicine. 2020;15:2685-2697. PMID: 32368049
- 6. Xiao J, Li W, et al. "Targeting 7-Dehydrocholesterol Reductase Integrates Cholesterol Metabolism and IRF3 Activation to Eliminate Infection." Immunity. 2020;52(1):109–122.e6. PMID: 31882361
- 7. Li Y, Yang B, et al. "Oral delivery of imatinib through galactosylated polymeric nanoparticles to explore the contribution of a saccharide ligand to absorption." Int J Pharm. 2019 Jul 9;568:118508. PMID: 31299337
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| 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. |
| Cell experiment [1]: | |
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Cell lines |
ergosterol-containing ciliary membranes |
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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. |
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Reacting condition |
12.7 μM |
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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. |
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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. |
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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. |
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Quality Control & MSDS
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Purity = 98.00%
- COA (Certificate Of Analysis)
- MSDS (Material Safety Data Sheet)
- Datasheet
Chemical structure
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