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F9765

Sigma-Aldrich

Filipin complex

powder, ≥70% (UV)

Synonym(s):

Filimarisin

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About This Item

CAS Number:
MDL number:
UNSPSC Code:
12352202
NACRES:
NA.77
Pricing and availability is not currently available.

Product Name

Filipin complex from Streptomyces filipinensis, ≥70% (UV)

biological source

Streptomyces sp. (Streptomyces filipinensis)

Quality Level

Assay

≥70% (UV)

form

powder

solubility

methanol: 9.80-10.20 mg/mL, clear to hazy, yellow to very deep greenish-yellow

antibiotic activity spectrum

fungi

Mode of action

cell membrane | interferes

storage temp.

−20°C

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

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General description

Chemical structure: macrolide

Application

Filipin complex from Streptomyces filipinensis has been used as a profluorescence probe to detect the free cholesterol in cell.[1][2][3]

Biochem/physiol Actions

Filipin is a polyene macrolide antibiotic and antifungal. The antifungal mechanism of action is unclear but may be due to altering membrane permeability and associated functions via binding to membrane sterols. Filipin binds to membrane sterols such as cholesterol, and it both inhibits prion protein (PrP) endocytosis and causes the release of PrP from the plasma membrane.
Filipin is a polyene macrolide antibiotic and antifungal. The antifungal mechanism of action is unclear but may be due to altering membrane permeability. Filipin binds to model crystalline phase lipid bilayers containing cholesterol, and to liquid phase bilayers with or without cholesterol, in an orientation that forms membrane pores.It both inhibits prion protein (PrP) endocytosis and causes the release of PrP from the plasma membrane.

Other Notes

Filipin contains 8 isomeric components, with filipin III as the major component.

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Pictograms

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Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Lipid profiles of prostate cancer cells
Sorvina A, et al.
Testing, 9(85), 35541-35541 (2018)
Lysosomal membrane stability plays a major role in the cytotoxic activity of the anti-proliferative agent, di-2-pyridylketone 4, 4-dimethyl-3-thiosemicarbazone (Dp44mT)
Gutierrez EM,et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1863(7), 1665-1681 (2016)
Analytical characterization of methyl-beta-cyclodextrin for pharmacological activity to reduce lysosomal cholesterol accumulation in Niemann-Pick disease type C1 cells
Li R, et al.
Assay and Drug Development Technologies, 15(4), 154-166 (2017)
Nada Kraševec et al.
Microorganisms, 8(12) (2020-12-17)
Aegerolysins are small lipid-binding proteins particularly abundant in fungi. Aegerolysins from oyster mushrooms interact with an insect-specific membrane lipid and, together with MACPF proteins produced by the same organism, form pesticidal pore-forming complexes. The specific interaction with the same membrane
Glenda M Halliday et al.
Brain : a journal of neurology, 128(Pt 11), 2654-2664 (2005-07-08)
The distribution and tempo of neuronal loss in Parkinson's disease correlates poorly with the characteristic and more widely spread intracellular changes associated with the disease process (Lewy bodies and Lewy neurites). To determine early intracellular changes in regions where cell

Questions

1–6 of 6 Questions  
  1. Which filipin is better to visualize cholesterol in hela cells by immunofluorescence - F9765 or F4767?

    1 answer
    1. Both F9765 and F4767 are suitable for determining cholesterol in cells. The F4767, Filipin III, is purified from Filipin. As it has a higher purity, it may offer a higher signal-to-noise ratio resulting in less background. These product have not been compared in side by side testing. It may be helpful to view the peer-reviewed knowledge articles to help with the appropriate selection:

      https://www.sigmaaldrich.com/search/f9765?focus=papers&page=1&perpage=30&sort=relevance&term=f9765&type=citation_search

      Helpful?

  2. What is the stability of filipin when dissolved in DMSO and stored at -20 degrees C (how long can it be stored like this)?

    1 answer
    1. This product has not been tested for stability in solution, however, product SAE0088 is a prepared 5/mg/mL solution in DMSO. This product is stable for at least 2 years at -20 deg. C. Similar stability would be expected for the F9765. See the link below to the product information sheet on the SAE0088 solution:
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/973/858/sae0088pis.pdf

      See the link below for a sample Certificate of Analysis for the prepared solution which includes the retest date:
      https://www.sigmaaldrich.com/certificates/sapfs/PROD/sap/certificate_pdfs/COFA/Q14/SAE0088-1ML0000207634.pdf

      Helpful?

  3. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

      Helpful?

  4. What is the difference between Filipin products F9765 and F4767?

    1 answer
    1. The product F9765 consists of a filipin complex. It is composed of 8 isomeric components, of which filipin III is the major component in the complex. F4767 consists of filipin III alone and is considered to be a better choice for staining.

      Helpful?

  5. What is the stability of stock solutions Product F9765, Filipin complex from Streptomyces filipinensis?

    1 answer
    1. Solutions of filipin in aqueous or organic solvents are not considered to be stable and it is recommended that they be prepared fresh and not stored as stock solutions.

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  6. How should Product F9765, Filipin complex from Streptomyces filipinensis, be solubilized?

    1 answer
    1. This product has low solubility in aqueous buffers. It should initially be reconstituted in DMSO at 1 mg/mL and then diluted into saline or an aqueous buffer of choice.

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