An active component of the filipin complex
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Alternative(s)
70440Filipin III
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Filipin III (solution)

Item No. 46790

Product Insert (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
Synonyms
  • NSC 3364
  • NSC 38092
Molecular Formula
C35H58O11
Formula Weight
654.8
Purity
≥90%
Formulation (Request formulation change)
A 1 mg/ml solution in DMSO
Solubility(Learn about Variance in Solubility)
DMSO: Soluble: ≥10 mg/ml
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-,29+,30+,31-,32+,33+,34-/m1/s1
InChi Key
IMQSIXYSKPIGPD-YQRUMEKGSA-N
Origin
Microbial
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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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(1), 61-70 (1973).