Filipin Explained

Filipin should not be confused with Filipinos.

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 mammalian 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]

Notes and References

  1. Whitfield, G. B. . Thomas D. Brock . Brock, T. D. . Ammann, A. . Gottlieb, D. . Carter, H. E. . Filipin, an Antifungal Antibiotic: Isolation and Properties . J. Am. Chem. Soc. . 1955 . 77 . 18. 4799–4801 . 10.1021/ja01623a032 . 101457395 .
  2. Ceder, O. . Ryhage, R. . The Structure of Filipin . Acta Chem. Scand. . 1964 . 18 . 558–561. 10.3891/acta.chem.scand.18-0558 . free .
  3. Bergy, M. E. . Eble, T. E. . Filipin Complex . Biochemistry . 1968 . 7 . 2. 653–659. 10.1021/bi00842a021 . 4296188 .
  4. Rychnovsky, S. D. . Richardson, T. I. . Relative and Absolute Configuration of Filipin III . Angew. Chem. Int. Ed. Engl. . 1995 . 34 . 11. 1227–1230 . 10.1002/anie.199512271 .