480-49-9

Basic information

• Product Name: FILIPIN III
• Synonyms: filimarisin;nsc3364;oxacyclooctacosa-17,19,21,23,25-pentaen-2-one,4,6,8,10,12,14,16,27-octahydroxy;u-5956;4S,6S,8S,10R,12R,14R,16S,27S-OCTAHYDROXY-3R-(1R-HYDROXY-HEXYL)17,28R-DIMETHYL-OXACYCLOOCTACOSA-17E,19E,21E,23E,25E-PENTAEN-2-ONE;FILIPIN III;filipin iii from streptomyces*filipinensis;4,6,8,10,12,14,16,27-Octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one
• CAS NO: 480-49-9
• Molecular Formula: C₃₅H₅₈O₁₁
• Molecular Weight: 654.83
• Product Categories: Enzyme Inhibitors;Enzyme Inhibitors by Type;Substrate Analogs
• Mol File: 480-49-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 163-180° (Bergy, Eble)
• Boiling Point: 913.9 °C at 760 mmHg
• Flash Point: 279.3 °C
• Appearance: /
• Density: 1.161 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: −20°C
• Solubility: Soluble in Methanol (up to 10 mg/ml)
• PKA: 12.77±0.70(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in methanol may be stored under inert gas at -20°C for up to 2 months.
• CAS DataBase Reference: FILIPIN III(CAS DataBase Reference)
• NIST Chemistry Reference: FILIPIN III(480-49-9)
• EPA Substance Registry System: FILIPIN III(480-49-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: RN9800000
• Hazardous Substances Data: 480-49-9(Hazardous Substances Data)

Usage

Description

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. The binding of cholesterol also decreases the intrinsic fluorescence of Filipin, and this property has also been used to detect cholesterol in membrane fractions.

Uses

Different sources of media describe the Uses of 480-49-9 differently. You can refer to the following data:
1. Filipin III is the major component of the filipin complex, a family of pentaene antifungal metabolites first isolated from Streptomyces filipinensis and reported by researchers at Upjohn in 1955. Filipin III is a potent broad spectrum antifungal agent that also exhibits antitumor and antiviral activities. Filipin III acts by binding cell membrane sterols, disrupting membrane integrity. This sterol selectivity has led to the use of filipin III as a routine diagnostic probe for quantifying cholesterol in mammalian cells.
2. 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. The binding of cholesterol also decreases the intrinsic fluorescence of Filipin, and this property has also been used to detect cholesterol in membrane fractions.[Cayman Chemical]
3. Produces arthritis rapidly in rabbits: Pras, Weissman, Drug Trade News, July 4, 1966, p 40; as a sterol probe in freeze-fracture cytochemistry.

Definition

ChEBI: A macrolide that is the major component of a mixture of four isomeric polyene macrolides isolated from Streptomyces filipinensis.

Biochem/physiol Actions

Filipin is a polyene macrolide antibiotic and antifungal. The antifungal mechanism of action may be due to altering membrane permeability and associated functions by binding to membrane sterols. Filipin inhibits prion protein (PrP) endocytosis and causes the release of PrP from the plasma membrane.

References

1) Smejkal and Hof (1994),?Cholesterol-specific probe for lipoproteins immobilized on nitrocellulose membranes; Biotechniques,?16?68 2) Bornig and Geyer ?(1974),?Staining of cholesterol with the fluorescent antibiotic “filipin”; Acta Histochemica,?50?110 3) Huo?et al. (2003),?Lipid rafts/caveolae are essential for insulin-like growth factor-1 receptor signaling during 3T3-L1 preadipocyte differentiation induction; J. Biol. Chem.,?278?11561 4) Marella?et al. (2002),?Filipin prevents pathological prion protein accumulation by reducing endocytosis and inducing cellular PrP release; J. Biol. Chem.,?277?25457

InChI:InChI=1/C35H58O11/c1-4-5-11-16-31(42)34-33(44)22-29(40)20-27(38)18-25(36)17-26(37)19-28(39)21-32(43)23(2)14-12-9-7-6-8-10-13-15-30(41)24(3)46-35(34)45/h6-10,12-15,24-34,36-44H,4-5,11,16-22H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,23-14+/t24-,25+,26-,27+,28-,29+,30+,31-,32+,33+,34-/m1/s1

Upstream product

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• 245681-54-3 (6S,7R)-7-benzoyloxy-6-(1,1-dimethylethyl)dimethylsiloxy-2,4-octadienal 
• 245681-49-6 (10S,11R)-11-hydroxy-10-(1,1-dimethylethyl)dimethylsiloxy-2,4,6,8-dodecatetraenal 
• 198955-38-3 1',26-bis-O-(1,1-dimethylethyl)dimethylsilyl-3,5:7,9:11,13-tris-O-(1-methylethylidine)-15-O-triisopropylsiloxy-filipin III 
• 198955-23-6 (3S,4S,5R)-5-(1,1-dimethylethyl)dimethylsiloxy-4-ethenyl-3-hydroxydecanoic acid, ethyl ester 
• 198955-18-9 [2(1R),2S,3S,5S,7S,9R,11R,13R]-16-diethylphosphono-2-(1-(1,1-dimethylethyl)dimethylsiloxy-hexyl)-3,5,7,9,11,13-hexahydroxy-3:5,7:9,11:13-tris-O-(1-methylethylidine)-15-oxo-heptadecanoic acid 
• 198955-34-9 (5R,7R,9R,11S,13S,15S,16S,17R)-2-diethylphosphono-17-O-(1,1-dimethylethyl)dimethylsilyl-16-ethenyl-5:7,9:11,13:15-tris-O-(1-methylethylidine)-3-oxo-docosane-5,7,9,11,13,15,17-heptol 
• 245681-60-1 [(4R,6R)-6-((4R,6S)-6-{(4S,6S)-6-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-vinyl-heptyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetaldehyde 
• 198955-33-8 (3S,5S,7S,9S,11S,13S,14S,15R)-15-O-(1,1-dimethylethyl)dimethylsilyl-14-ethenyl-3:5,7:9,11:13-tris-O-(1-methylethylidine)-eicosane-1,3,5,7,9,11,13,15-octol 
• 198955-19-0 (4S,5S,6R)-2,4-dihydroxy-6-(1,1-dimethylethyl)dimethylsiloxy-5-ethenyl-2,4-O-(1-methylethylidine)-undecanenitrile 
• 198955-22-5 (4S,5R)-5-(1,1-dimethylethyl)dimethylsiloxy-4-ethenyl-3-oxodecanoic acid, ethyl ester 
• 245681-57-6 2,2-Dimethyl-propionic acid (2S,3R)-3-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-octyl ester 
• 245681-56-5 2,2-Dimethyl-propionic acid (2S,3R)-3-hydroxy-2-vinyl-octyl ester 
• 198955-21-4 (3S,4R)-3-O-(1,1-dimethylethyl)dimethylsilyl-3-hydroxymethyl-1-nonen-4-ol 

Downstream Products

• 165329-49-7 1',3:5,7:9,11:13,15-tetrakis-O-(1-methylethylidene)filipin III 

Relevant articles and documents

Total synthesis of Filipin III

Filipin III (1), a polyene macrolide antibiotic, has been synthesized for the first time. The polyol chain was assembled using a stereoselective carbon-carbon bond forming strategy previously developed in our lab: a cyanohydrin acetonide alkylation and reductive decyanation sequence. The polyene segment was prepared from L-ascorbic acid. These two components were coupled using Yamaguchi's esterification, and cyclized with an intramolecular Horner-Emmons reaction to form a trisubstituted alkene. Stereoselective reduction followed by deprotection gave filipin III. This highly convergent approach to filipin III represents the first total synthesis of a methylpentaene macrolide antibiotic.