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

FILIPIN III, a macrolide and the major component of the filipin complex, is a potent broad-spectrum antifungal agent derived from Streptomyces filipinensis. It exhibits antifungal, antitumor, and antiviral activities by binding to cell membrane sterols, disrupting membrane integrity. This sterol selectivity has made it a valuable diagnostic probe for quantifying cholesterol in mammalian cells.

Uses

Used in Antifungal Applications:
FILIPIN III is used as an antifungal agent for its potent broad-spectrum activity against various fungal infections.
Used in Antitumor Applications:
FILIPIN III is used as an antiviral agent for its demonstrated antitumor properties.
Used in Diagnostics:
FILIPIN III is used as a diagnostic probe for quantifying cholesterol in mammalian cells due to its sterol selectivity and ability to bind to cholesterol in membranes.
Used in Research:
FILIPIN III is used as a sterol probe in freeze-fracture cytochemistry for the localization and measurement of cholesterol in cells.
Used in Arthritis Research:
FILIPIN III is used to produce arthritis rapidly in rabbits for research purposes, as reported in Drug Trade News on July 4, 1966.

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

• 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 
• 245681-58-7 (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-vinyl-octanal 
• 198955-20-3 (3S,4R)-3-hydroxymethyl-1-nonen-4-ol 
• 97589-09-8 (2R,3R)-2,3-epoxy-1-octanol 
• 198955-37-2 1',26-bis-O-(1,1-dimethylethyl)dimethylsilyl-3,5:7,9:11,13-tris-O-(1-methylethylidine)filipin III 

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.