Filipin

Filipin III
Names
IUPAC 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-[(1R)-1-hydroxyhexyl]-17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one
Identifiers
480-49-9 YesY
ChemSpider 21106312 YesY
Jmol interactive 3D Image
KEGG D04186 YesY
MeSH Filipin
PubChem 6433194
UNII 87Z59R7D14 YesY
Properties
C35H58O11
Molar mass 654.84 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Filipin is a mixture of chemical compounds first isolated by chemists at the Upjohn company in 1955 from the mycelium and culture filtrates of a previously unknown actinomycete, Streptomyces filipinensis.[1] It was discovered in a soil sample collected in the Philippine Islands, hence 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.

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 nystatin 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)

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.[2][3]

The relative and absolute stereochemistry of filipin III was determined by 13C NMR acetonide analysis.[4]

References

  1. Whitfield, G. B.; Brock, T. D.; Ammann, A.; Gottlieb, D.; Carter, H. E. (1955). "Filipin, an Antifungal Antibiotic: Isolation and Properties". J. Am. Chem. Soc. 77 (18): 4799–4801. doi:10.1021/ja01623a032.
  2. Ceder, O.; Ryhage, R. (1964). "The Structure of Filipin". Acta Chem. Scand. 18: 558–561. doi:10.3891/acta.chem.scand.18-0558.
  3. Bergy, M. E.; Eble, T. E. (1968). "Filipin Complex". Biochem. 7 (2): 653–659. doi:10.1021/bi00842a021.
  4. Rychnovsky, S. D.; Richardson, T. I. (1995). "Relative and Absolute Configuration of Filipin III". Angew. Chem. Int. Ed. Engl. 34 (11): 1227–1230. doi:10.1002/anie.199512271.

External links

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