Filipin

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Filipin III
FilipinIII.png
Names
Preferred 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-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.164.904 OOjs UI icon edit-ltr-progressive.svg
KEGG
MeSH Filipin
PubChem CID
UNII
  • InChI=1S/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 Yes check.svgY
    Key: IMQSIXYSKPIGPD-NKYUYKLDSA-N Yes check.svgY
  • 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
    Key: IMQSIXYSKPIGPD-NKYUYKLDBD
  • CCCCC[C@H](O)[C@H]1C(=O)O[C@H](C)[C@@H](O)\C=C\C=C\C=C\C=C\C=C(/C)[C@@H](O)C[C@H](O)C[C@H](O)C[C@H](O)C[C@H](O)C[C@H](O)C[C@@H]1O
Properties
C35H58O11
Molar mass 654.838 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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.[ citation needed ]

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)[ citation needed ]

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. S2CID   101457395.
  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". Biochemistry. 7 (2): 653–659. doi:10.1021/bi00842a021. PMID   4296188.
  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.
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