An active component of the filipin complex
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Filipin III

Item No. 70440

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4S,6S,8S,10R,12R,14R,16S,27S-octahydroxy-3R-(1R-hydroxy-hexyl)17,28R-dimethyl-oxacyclooctacosa-17E,19E,21E,21E,23E,25E-pentaen-2-one
CAS Number
480-49-9
Molecular Formula
C35H58O11
Formula Weight
654.8
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:4): 0.2 mg/mlEthanol: 1 mg/ml
λmax
323, 339, 357 nm
SMILES
O[C@@H]1/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)C1)=O
InChi Code
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-
InChi Key
IMQSIXYSKPIGPD-YQRUMEKGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $131

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    1 mg

    $197

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    5 mg

    $721

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    Product Description

    Filipin III is a polyene and an active component of the polyene antibiotic filipin complex (Item No. 25073).1 It is active against various fungi, including B. dermatitidis, C. neoformans, H. capsulatum, C. albicans, and T. mentagrophytes (MICs = 1-10 μg/ml). Filipin III induces hemolysis of isolated rabbit erythrocytes (EC50 = 0.8 µg/ml).2 It induces apoptosis in HaCaT keratinocytes in a concentration-dependent manner.3 Filipin III binds to cholesterol and has been used to fluorescently label sterols in biological structures.4,5 The filipin complex has excitation maxima of 338 and 357 nm and an emission maxima of 480 nm.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bergy, M.E., and Eble, T.E. The filipin complex. Biochemistry 7(2), 653-659 (1968).

    2. Sessa, G., and Weissmann, G. Effects of four components of the polyene antibiotic, filipin, on phospholipid spherules (liposomes) and erythrocytes. The Journal of Biological Chemisty 243(16), 4364-4371 (1968).

    3. Gniadecki, R. Depletion of membrane cholesterol causes ligand-independent activation of Fas and apoptosis. Biochem. Biophys. Res. Commun. 320(1), 165-169 (2004).

    4. Bittman, R., and Fischkoff, S.A. Fluorescence studies of the binding of the polyene antibiotics filipin 3, amphotericin B, nystatin, and lagosin to cholesterol. Proc. Natl. Acad. Sci. USA 69(12), 3795-3799 (1972).

    5. Boutté, Y., Men, S., and Grebe, M. Fluorescent in situ visualization of sterols in Arabidopsis roots. Nat. Protoc. 6(4), 446-456 (2011).

    6. Drabikowski, W., Lagwinska, E., and Sarzala, M.G. Filipin as a fluorescent probe for the location of cholesterol in the membranes of fragmented sarcoplasmic reticulum. Biochim. Biophys. Acta 291, 61-70 (1973).

    Product Citations

    Ianniello, Z., Lu, H., Quijano, E., et al. Harnessing AxDNA for precision exatecan delivery in cancer: A novel antibody-drug conjugate approach. Mol. Cancer 24(1), 253 (2025).

    Gehne, N., Lamik, A., Lehmann, M., et al. Cross-over endocytosis of claudins is mediated by interactions via their extracellular loops. PLoS One 12(8), e0182106 (2017).

    Johndrow, C., Nelson, R., Tanowitz, H., et al. Trypanosoma cruzi infection results in an increase in intracellular cholesterol. Microbes Infect. 16(4), 337-344 (2014).

    Matsushima, T., Saito, Y., Elliott, J.I., et al. Membrane-microdomain localization of amyloid β-precursor protein (APP) C-terminal fragments is regulated by phosphorylation of the cytoplasmic Thr668 residue. The Journal of Biological Chemisty 287(23), 19715-19724 (2012).

    Zheng, W., Reem, R.E., Omarova, S., et al. Spatial distribution of the pathways of cholesterol homeostasis in human retina. PLoS One 7(5), e37926 (2012).

    Omarova, S., Charvet, C.D., Reem, R.E., et al. Abnormal vascularization in mouse retina with dysregulated retinal cholesterol homeostasis. J. Clin. Invest. 122(8), 3012-3023 (2012).