Filipin III

- Overview
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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].
    
    [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.
- Properties
  - Categories
    
    cholesterol-binding, fluorescing antibiotic used for the detection of lipoproteins
    
    Alternative 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
    
    CAS Number
    
    480-49-9
    
    Molecular Formula
    
    C35H58O11
    
    Molecular Weight
    
    654.83
    
    Appearance
    
    A crystalline solid
    
    Purity
    
    98.00%
    
    Solubility
    
    Soluble in DMSO
    
    Storage
    
    Store at -20°C
    
    SMILES
    
    O[[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
    
    * For Research Use Only
- Reference
  - 1. 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
    2. 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
    3. 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
    4. 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
    5. 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
    6. Siu FY, Ye S, et al. "Galactosylated PLGA nanoparticles for the oral delivery of resveratrol: enhanced bioavailability and in vitro anti-inflammatory activity." Int J Nanomedicine. 2018 Jul 13;13:4133-4144. PMID:30038494
    7. Zu-Guo Zheng, Chong Lu, et al. "Praeruptorin B improves diet-induced hyperlipidemia and alleviates insulin resistance via regulating SREBP signaling pathway." RSC Adv., 2018, 8, 354.

Documents

COA (Certificate Of Analysis)

MSDS (Material Safety Data Sheet)

Datasheet

Filipin III

Background

Documents

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