A neutral polyene with antifungal activity
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Filipin Complex

Item No. 25073

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
11078-21-0
Synonyms
  • U-5956
Molecular Formula
C35H58O11 (for Filipin III)
Formula Weight
654.8
Purity
≥95%
Emission
480 nm
Excitation
338 nm
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O[C@@H]1/C(C)=C/C=C/C=C/C=C/C=C/C[C@@H](C)OC([C@@](CCCCCC)([H])[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C1)=O.O[C@@H]2/C(C)=C/C=C/C=C/C=C/C=C/[C@H](O)[C@@H](C)OC([C@@]([C@H](O)CCCCC)([H])[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C2)=O.O[C@@H]3/C(C)=C/C=C/C=C/C=C/C=C/[C@H](O)[C@@H](C)OC([C@@](CCCCCC)([H])[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C3)=O
InChi Code
InChI=1S/C35H58O11.C35H58O10.C35H58O9/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;1-4-5-6-13-16-31-34(43)23-30(40)21-28(38)19-26(36)18-27(37)20-29(39)22-33(42)24(2)15-12-10-8-7-9-11-14-17-32(41)25(3)45-35(31)44;1-4-5-6-15-18-32-34(42)24-31(40)22-29(38)20-27(36)19-28(37)21-30(39)23-33(41)25(2)16-13-11-9-7-8-10-12-14-17-26(3)44-35(32)43/h6-10,12-15,24-34,36-44H,4-5,11,16-22H2,1-3H3;7-12,14-15,17,25-34,36-43H,4-6,13,16,18-23H2,1-3H3;7-14,16,26-34,36-42H,4-6,15,17-24H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,23-14+;8-7+,11-9+,12-10+,17-14+,24-15+;9-7+,10-8+,13-11+,14-12+,25-16+/t24-,25+,26-,27+,28-,29+,30+,31-,32+,33+,34-;25-,26+,27-,28+,29-,30+,31-,32+,33+,34+;26-,27+,28-,29+,30-,31+,32-,33+,34+/m111/s1
InChi Key
IHAFZJMCJAUNQT-XPOKRYMLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    25 mg

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    50 mg

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    Product Description

    Filipin complex is a neutral polyene originally isolated from S. filipinensis with antifungal activity.1 It inhibits cell growth as well as mitochondrial terminal electron transport in S. cerevisiae when used at a concentration of 135 µg/ml. Filipin complex binds to various sterols, particularly 24α-methyl cholesterol (Item no. 17344), 24α-ethyl cholesterol (Item no. 11756), and cholesterol, in aqueous solutions and in fungal cell membranes when used at a concentration of 50 µg/ml, inducing membrane pit formation and leakage of cell contents.2,3,4 It is a fluorescent compound that has been used to label sterols within biological structures for imaging.3,5,6,7 Filipin complex displays excitation/emission maxima of 338/480 nm, respectively.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shaw, P.D., Allam, A.M., and Gottlieb, D. Effect of filipin on the terminal electron transport system of Saccharomyces cerevisiae. Biochim. Biophys. Acta 89(1), 33-41 (1964).

    2. Kitajima, Y., Sekiya, T., and Nozawa, Y. Freeze-fracture ultrastructural alterations induced by filipin, pimaricin, nystatin and amphotericin B in the plasmia membranes of Epidermophyton, Saccharomyces and red complex-induced membrane lesions. Biochim. Biophys. Acta 455(2), 452-465 (1976).

    3. Miller, R.G. Mini Review. The use and abuse of filipin to localize cholesterol in membranes. Cell Biol. Int. Rep. 8(7), 519-535 (1984).

    4. Kleinschmidt, M.G., and Chough, K.S. Effect of filipin on liposomes prepared with different types of steroids. Plant Physiol. 49(5), 852-856 (1972).

    5. Castanho, M.A., Coutinho, A., and Prieto, M.J. Absorption and fluorescence spectra of polyene antibiotics in the presence of cholesterol. The Journal of Biological Chemisty 267(1), 204-209 (1992).

    6. Sekiya, T., Takenawa, T., and Nozawa, H. Reorganization of membrane cholesterol during membrane fusion in myogenesis in vitro: A study using the filipin-cholesterol complex. Cell Struct. Funct. 9(2), 143-155 (1984).

    7. Bridgman, P.C., and Nakajima, Y. Distribution of filipin-sterol complexes on cultured muscle cells: Cell-substratum contact areas associated with acetylcholine receptor clusters. J. Cell Biol. 96(2), 363-372 (1983).