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{{distinguish|Filipinos}}
{{chembox {{chembox
| Verifiedfields = changed | Watchedfields = changed
| Name = Filipin III
⚫ | UNII_Ref = {{fdacite|changed|FDA}}
⚫ | verifiedrevid = 445258108
⚫ | UNII = 87Z59R7D14
⚫ | ImageFile=FilipinIII.png
⚫ | verifiedrevid = 400093006
⚫ | ImageSize=250
⚫ |ImageFile=FilipinIII.png
⚫ | PIN=(3''R'',4''S'',6''S'',8''S'',10''R'',12''R'',14''R'',16''S'',17''E'',19''E'',21''E'',23''E'',25''E'',27''S'',28''R'')-4,6,8,10,12,14,16,27-Octahydroxy-3--17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
⚫ |ImageSize=250
⚫ | OtherNames=
⚫ |IUPACName=(3''R'',4''S'',6''S'',8''S'',10''R'',12''R'',14''R'',16''S'',17''E'',19''E'',21''E'',23''E'',25''E'',27''S'',28''R'')-4,6,8,10,12,14,16,27-octahydroxy-3--17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one
⚫ |OtherNames=
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | 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
⚫ | 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 | InChIKey = IMQSIXYSKPIGPD-NKYUYKLDBD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 15: Line 17:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IMQSIXYSKPIGPD-NKYUYKLDSA-N | StdInChIKey = IMQSIXYSKPIGPD-NKYUYKLDSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=480-49-9 | CASNo=480-49-9
| PubChem=6433194 | PubChem=6433194
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=21106312 | ChemSpiderID=21106312
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04186 | KEGG = D04186
| SMILES = CCCCC(O)1C(=O)O(C)(O)\C=C\C=C\C=C\C=C\C=C(/C)(O)C(O)C(O)C(O)C(O)C(O)C1O | SMILES = CCCCC(O)1C(=O)O(C)(O)\C=C\C=C\C=C\C=C\C=C(/C)(O)C(O)C(O)C(O)C(O)C(O)C1O
| MeSHName=Filipin | MeSHName=Filipin
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
|C=35|H=58|O=11 | C=35 | H=58 | O=11
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}
'''Filipin''' is a chemical compound. It was isolated by chemists at the ] company in 1955 from the mycelium and culture filtrates of a previously unknown actinomycete, '']'', that was discovered in a soil sample collected in the ]. Thus the name Filipin. The isolate possessed potent antifungal activity. It was identified as a polyene macrolide based on its characteristic ] and ] spectra. '''Filipin''' is a mixture of chemical compounds first isolated by chemists at the ] company in 1955 from the mycelium and culture filtrates of a previously unknown ], '']''.<ref>{{cite journal |author1=Whitfield, G. B. |author2-link=Thomas D. Brock |author2=Brock, T. D. |author3=Ammann, A. |author4=Gottlieb, D. |author5=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 | doi=10.1021/ja01623a032 |s2cid=101457395 }}</ref> It was discovered in a soil sample collected in the ], hence the name filipin. The isolate possessed potent antifungal activity. It was identified as a polyene macrolide based on its characteristic ] and ] spectra.


==Functions== ==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 ] B and ] A1 which form sterol-dependent ], filipin is thought to be a simple membrane disrupter. Since Filipin is highly ] and binds specifically to ] 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 ]. Although the ] exhibit potent antifungal activity, most are too toxic for therapeutic applications, with the exceptions of ] and ]. Unlike amphotericin B and nystatin A1 which form sterol-dependent ], filipin is thought to be a simple membrane disrupter. Since filipin is highly ] and binds specifically to ], 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 ].{{cn|date=December 2022}}


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) It is also used in cellular biology as an inhibitor of the raft/caveolae endocytosis pathway on mammalian cells (at concentrations around 3&nbsp;μg/mL){{cn|date=December 2022}}


==Types== ==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. 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.<ref>{{cite journal |author1=Ceder, O. |author2=Ryhage, R. | title=The Structure of Filipin | journal=Acta Chem. Scand. | year=1964 | volume=18 | pages=558–561| doi=10.3891/acta.chem.scand.18-0558 | doi-access=free }}</ref><ref>{{cite journal |author1=Bergy, M. E. |author2=Eble, T. E. | title=Filipin Complex | journal=Biochemistry | year=1968 | volume=7 | issue= 2| pages=653–659| doi=10.1021/bi00842a021 |pmid=4296188 }}</ref>
* The major component, filipin III, has the structure which was proposed by Ceder and Ryhage for the filipin complex. * 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. * Filipin I, which has been difficult to characterize, is probably a mixture of several components each having two hydroxyl groups fewer than filipin III.
* ] and ] data indicate that Filipin II is 1'-deoxy-filipin III. * ] and ] 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. * 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 ] of filipin III was determined by ]. The relative and absolute ] of filipin III was determined by ].<ref>{{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 | doi=10.1002/anie.199512271 }}</ref>


==References== ==References==
{{reflist}}
*{{cite journal | author=Whitfield, G. B.; ]; 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= | pages=4799–4801 | url= | doi=10.1021/ja01623a032 }}
*{{cite journal | author=Ceder, O.; 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 }}
*{{cite journal | author=Bergy, M. E.; Eble, T. E. | title=Filipin Complex | journal=Biochem. | year=1968 | volume=7 | issue= | pages=653–659| url= | doi=10.1021/bi00842a021 }}
*{{cite journal | author=Rychnovsky, S. D.; Richardson, T. I. | title=Relative and Absolute Configuration of Filipin III | journal=Angew. Chem., Int. Ed. Engl. | year=1995 | volume=34 | issue= | pages=1227–1230 | url= | doi=10.1002/anie.199512271 }}


==External links== ==External links==
* {{MeshName|Filipin}} * {{MeshName|Filipin}}


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