词条 | Filipin |
释义 |
| Watchedfields = changed | Name = Filipin III | verifiedrevid = 445258108 | ImageFile=FilipinIII.png | ImageSize=250 | IUPACName=(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 | OtherNames= |Section1={{Chembox Identifiers | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 87Z59R7D14 | 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 | InChIKey = IMQSIXYSKPIGPD-NKYUYKLDBD | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = IMQSIXYSKPIGPD-NKYUYKLDSA-N | CASNo_Ref = {{cascite|correct|??}} | CASNo=480-49-9 | PubChem=6433194 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID=21106312 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D04186 | 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 | MeSHName=Filipin |Section2={{Chembox Properties | C=35 | H=58 | O=11 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} 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. FunctionsAlthough 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) TypesFilipin 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] References1. ^{{cite journal | author=Whitfield, G. B.; Brock, T. D.; Ammann, A.; Gottlieb, D.; Carter, H. E. | title=Filipin, an Antifungal Antibiotic: Isolation and Properties | journal=J. Am. Chem. Soc. | year=1955 | volume=77 | issue= 18| pages=4799–4801 | url= | doi=10.1021/ja01623a032 }} 2. ^{{cite journal |author1=Ceder, O. |author2=Ryhage, R. | title=The Structure of Filipin | journal=Acta Chem. Scand. | year=1964 | volume=18 | issue= | pages=558–561| url= | doi=10.3891/acta.chem.scand.18-0558 }} 3. ^{{cite journal |author1=Bergy, M. E. |author2=Eble, T. E. | title=Filipin Complex | journal=Biochemistry | year=1968 | volume=7 | issue= 2| pages=653–659| url= | doi=10.1021/bi00842a021 }} 4. ^{{cite journal |author1=Rychnovsky, S. D. |author2=Richardson, T. I. | title=Relative and Absolute Configuration of Filipin III | journal=Angew. Chem. Int. Ed. Engl. | year=1995 | volume=34 | issue= 11| pages=1227–1230 | url= | doi=10.1002/anie.199512271 }} External links
3 : Macrolides|Antifungals|Polyenes |
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