filipin

Filipin III
	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
CAS number	480-49-9
PubChem	6433194
ChemSpider	21106312
KEGG	D04186
MeSH	Filipin
Jmol-3D images	Image 1
	SMILES 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 ;
	InChI 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 ; Key: IMQSIXYSKPIGPD-NKYUYKLDSA-N 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 ;
Properties
Molecular formula	C35H58O11
Molar mass	654.83 g mol−1
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

フィリピン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/04/17 06:47:48」(JST)

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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 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 spectrometry and 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 of filipin III was determined by 13C NMR acetonide analysis.^[4]

References

^ 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.
^ Ceder, O.; Ryhage, R. (1964). "The Structure of Filipin". Acta Chem. Scand. 18: 558–561. doi:10.3891/acta.chem.scand.18-0558.
^ Bergy, M. E.; Eble, T. E. (1968). "Filipin Complex". Biochem. 7 (2): 653–659. doi:10.1021/bi00842a021.
^ 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

Filipin at the US National Library of Medicine Medical Subject Headings (MeSH)

UpToDate Contents

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1. ニーマン・ピック病の概要 overview of niemann pick disease

English Journal

Transport of stearic acid-based solid lipid nanoparticles (SLNs) into human epithelial cells.

Shah RM1, Rajasekaran D1, Ludford-Menting M2, Eldridge DS1, Palombo EA1, Harding IH3.
Colloids and surfaces. B, Biointerfaces.Colloids Surf B Biointerfaces.2016 Apr 1;140:204-12. doi: 10.1016/j.colsurfb.2015.12.029. Epub 2015 Dec 28.
Development of drug delivery systems, as much as the drug molecule itself, is an important consideration for improving drug absorption and bioavailability. The mechanisms by which drug carriers enter target cells can differ depending on their size, surface properties and components. Solid lipid nano
PMID 26764103

Clinical Spectrum and Genetic Variability in Bulgarian Patients with Niemann-Pick Disease Type C.

Chamova T1, Kirov A, Guergueltcheva V, Todorov XI, Bojinova V, Zhelyazkova S, Samuel J, Radionova M, Sarafov S, Cherninkova S, Krastev S, Todorova XL, Tournev I.
European neurology.Eur Neurol.2016 Feb 25;75(3-4):113-123. [Epub ahead of print]
BACKGROUND: Niemann-Pick disease type C (NP-C) is a rare autosomal-recessive lysosomal storage disorder caused by mutations in either the NPC1 (in 95% of cases) or the NPC2 gene.METHODS: In a prospective, observational cohort study, all Bulgarian patients diagnosed with NP-C to date (since 2010) und
PMID 26910362

Cholesterol-Loaded Cyclodextrin Increases the Cholesterol Content of Goat Sperm To Improve Cold- and Osmotic-Resistance and Maintain Sperm Function after Cryopreservation.

Salmon VM, Leclerc P, Bailey JL.
Biology of reproduction.Biol Reprod.2016 Feb 17. pii: biolreprod.115.128553. [Epub ahead of print]
The success of semen cryopreservation depends on sperm membrane integrity and function after thawing. Cholesterol-loaded cyclodextrin (CLC) is used for in vitro incorporation of cholesterol to protect cells against cold temperatures. We hypothesized that CLC treatment also enhances sperm cholesterol
PMID 26888968

Japanese Journal

Savant症候群が特徴的であった成人発症のニーマン・ピック病C型variant biochemical phenotypeの1例

臨床神経学 56(6), 424-429, 2016
NAID 130005158851

Savant症候群が特徴的であった成人発症のニーマン・ピック病C型variant biochemical phenotypeの1例

臨床神経学 advpub(0), 2016
NAID 130005151292

ACID SPHINGOMYELINASE IS ESSENTIAL FOR CHOLESTEROL-REDUCING AGENTS TO POSITIVELY AFFECT ACCUMULATED FREE CHOLESTEROL IN NIEMANN-PICK DISEASE TYPE C FIBROBLASTS