Filipin
Encyclopedia
Filipin is a chemical compound. It was isolated by chemists at the Upjohn
company in 1955 from the mycelium and culture filtrates of a previously unknown actinomycete, Streptomyces filipinensis, that was discovered in a soil sample collected in the Philippine Islands. Thus the name Filipin. The isolate possessed potent antifungal activity. It was identified as a polyene macrolide based on its characteristic UV-Vis and IR
spectra.
A1 which form sterol-dependent ion channels, filipin is thought to be a simple membrane disrupter. Since Filipin is highly fluorescent
and binds specifically to cholesterol
it has found widespread use as a histochemical stain for cholesterol. This method of detecting cholesterol in cell membranes is used clinically in the study and diagnosis of Type C Niemann-Pick disease
.
It is also used in cellular biology as an inhibitor of the raft/caveolae endocytosis pathway on mamallian cells (at concentrations around 3 µg/mL)
The relative and absolute stereochemistry
of filipin III was determined by 13C NMR acetonide analysis.
Upjohn
The Upjohn Company was a pharmaceutical manufacturing firm founded in 1886 in Kalamazoo, Michigan by Dr. William E. Upjohn, an 1875 graduate of the University of Michigan medical school. The company was originally formed to make friable pills, which were specifically designed to be easily digested...
company in 1955 from the mycelium and culture filtrates of a previously unknown actinomycete, Streptomyces filipinensis, that was discovered in a soil sample collected in the Philippine Islands. Thus the name Filipin. The isolate possessed potent antifungal activity. It was identified as a polyene macrolide based on its characteristic UV-Vis and IR
Infrared
Infrared light is electromagnetic radiation with a wavelength longer than that of visible light, measured from the nominal edge of visible red light at 0.74 micrometres , and extending conventionally to 300 µm...
spectra.
Functions
Although the polyene macrolide antibiotics exhibit potent antifungal activity, most are too toxic for therapeutic applications, with the exceptions of amphotericin B and nystatin A1. Unlike amphotericin B and nystatinNystatin
Nystatin is a polyene antifungal medication to which many molds and yeast infections are sensitive, including Candida. Due to its toxicity profile, there are currently no injectable formulations of this drug on the US market...
A1 which form sterol-dependent ion channels, filipin is thought to be a simple membrane disrupter. Since Filipin is highly fluorescent
Fluorescence
Fluorescence is the emission of light by a substance that has absorbed light or other electromagnetic radiation of a different wavelength. It is a form of luminescence. In most cases, emitted light has a longer wavelength, and therefore lower energy, than the absorbed radiation...
and binds specifically to cholesterol
Cholesterol
Cholesterol is a complex isoprenoid. Specifically, it is a waxy steroid of fat that is produced in the liver or intestines. It is used to produce hormones and cell membranes and is transported in the blood plasma of all mammals. It is an essential structural component of mammalian cell membranes...
it has found widespread use as a histochemical stain for cholesterol. This method of detecting cholesterol in cell membranes is used clinically in the study and diagnosis of Type C Niemann-Pick disease
Niemann-Pick disease
Niemann–Pick disease refers to a group of fatal inherited metabolic disorders that are included in the larger family of lysosomal storage diseases .-Signs and symptoms:Symptoms are related to the organs in which they accumulate...
.
It is also used in cellular biology as an inhibitor of the raft/caveolae endocytosis pathway on mamallian cells (at concentrations around 3 µg/mL)
Types
Filipin is a mixture of four components - filipin I (4%), II (25%), III (53%), and IV (18%) - and should be referred to as the filipin complex.- The major component, filipin III, has the structure which was proposed by Ceder and Ryhage for the filipin complex.
- Filipin I, which has been difficult to characterize, is probably a mixture of several components each having two hydroxyl groups fewer than filipin III.
- Mass spectrometryMass spectrometryMass spectrometry is an analytical technique that measures the mass-to-charge ratio of charged particles.It is used for determining masses of particles, for determining the elemental composition of a sample or molecule, and for elucidating the chemical structures of molecules, such as peptides and...
and NMRNMRNMR may refer to:Applications of Nuclear Magnetic Resonance:* Nuclear magnetic resonance* NMR spectroscopy* Solid-state nuclear magnetic resonance* Protein nuclear magnetic resonance spectroscopy* Proton NMR* Carbon-13 NMR...
data indicate that Filipin II is 1'-deoxy-filipin III. - Filipin IV is isomeric to filipin III. Their NMR spectra are nearly identical with the major difference being the splitting pattern of the proton at C2. This indicates that filipin IV is probably epimeric to filipin III at either C1' or C3.
The relative and absolute stereochemistry
Stereochemistry
Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms within molecules. An important branch of stereochemistry is the study of chiral molecules....
of filipin III was determined by 13C NMR acetonide analysis.