| Identification | Back Directory | [Name]
FILIPIN III | [CAS]
480-49-9 | [Synonyms]
u-5956
nsc3364
Nsc38092
27-lactone
filimarisin
FILIPIN III
15-Deoxylagosin
1'-epi-Filipin IV
1'-Hydroxyfilipin II
FILIPIN III USP/EP/BP
1',26-Dihydroxyfilipin I
24-Octacosapentenoic acid
28-dimethyl--3-(1-hydroxyhexyl)-1
filipin iii from streptomyces*filipinensis
27-nonahydroxy-2-(1-hydroxyhexyl)-16-methyl-
oxacyclooctacosa-17,19,21,23,25-pentaen-2-one,4,6,8,10,12,14,16,27-octahydroxy
4,6,8,10,12,14,16,27-Octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one
16;20;22;24-OCTACOSAPENTENOIC ACID; 3;5;7;9;11;13;15;26;27-NONAHYDROXY-2-(1-HYDROXYHEXYL)-16-METHYL-; 27-LACTONE
Oxacyclooctacosa-17,19,21,23,25-pentaen-2-one, 4,6,8,10,12,14,16,27-octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyl-
16,18,20,22,24-Octacosapentenoic acid, 3,5,7,9,11,13,15,26,27-nonahydroxy-2-(1-hydroxyhexyl)-16-methyl-, 27-lactone
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
(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-[(1R)-1-hydroxyhexyl]-17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one
(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-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
Oxacyclooctacosa-17,19,21,23,25-pentaen-2-one, 4,6,8,10,12,14,16,27-octahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-, (3R,4S,6S,8S,10R,12R,14R,16S,17E,19E,21E,23E,25E,27S,28R)- | [Molecular Formula]
C35H58O11 | [MDL Number]
MFCD00466923 | [MOL File]
480-49-9.mol | [Molecular Weight]
654.83 |
| Chemical Properties | Back Directory | [Melting point ]
163-180° (Bergy, Eble) | [alpha ]
D25 -245° (c = 0.8 in DMF) | [Boiling point ]
913.9±65.0 °C(Predicted) | [density ]
1.161±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Soluble in Methanol (up to 10 mg/ml) | [form ]
solid | [pka]
12.77±0.70(Predicted) | [color ]
White or light yellow | [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. |
| Hazard Information | Back Directory | [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.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 | [Uses]
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] | [Uses]
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. | [Uses]
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. | [storage]
Store at -20°C, protect from light. | [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 |
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