Molecular structure of Filipin III, CAS Number: 480-49-9
Filipin III (CAS 480-49-9)
See product citations (26)
Alternate Names:
Filipin III also known as 16,20,22,24-Octacosapentenoic acid; 3,5,7,9,11,13,15,26,27-nonahydroxy-2-(1-hydroxyhexyl)-16-methyl-, 27-lactone; NSC3364; NSC-3364
Application:
Filipin III is a cholesterol-binding, fluorescing antibiotic used to detect cholesterol in membranes through freeze fracture electron microscopy
CAS Number:
480-49-9
Purity:
>85%
Molecular Weight:
654.83
Molecular Formula:
C35H58O11
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Filipin III is a pentaene macrolide antibiotic and the predominant isomer of four isomeric polyene macrolides isolated from cultures of S. filipinensis. Due to Filipin III′s ability to fluoresce and bind to cholesterol, the compound has been used to detect cholesterol in membranes through freeze fracture electron microscopy and through decreased fluorescence of Filipin III upon binding. It has also been used in tobacco cells and observed to activate ligand-independent signaling responses. Through Filipin III′s cholesterol sequestering activity, it can disrupt the lipid rafts in both normal and transformed keratinocytes resulting in inhibition of the AKT pathway. Filipin III is the major component of 8 isomeric components in filipin.
Filipin III (CAS 480-49-9) References
- A photophysical study of the polyene antibiotic filipin. Self-aggregation and filipin--ergosterol interaction. | Loura, LM., et al. 2001. Biochim Biophys Acta. 1510: 125-35. PMID: 11342153
- Permeabilizing action of filipin III on model membranes through a filipin-phospholipid binding. | Milhaud, J. 1992. Biochim Biophys Acta. 1105: 307-18. PMID: 1375101
- Filipin orientation revealed by linear dichroism. Implication for a model of action. | Lopes, SC., et al. 2004. J Am Chem Soc. 126: 5396-402. PMID: 15113211
- Absorption and fluorescence spectra of polyene antibiotics in the presence of cholesterol. | Castanho, MA., et al. 1992. J Biol Chem. 267: 204-9. PMID: 1730589
- Inhibition of Akt signaling by exclusion from lipid rafts in normal and transformed epidermal keratinocytes. | Calay, D., et al. 2010. J Invest Dermatol. 130: 1136-45. PMID: 20054340
- [Mechanism of action of macrolide antibiotic filipin on cell and lipid membranes]. | Samedova, AA. and Kasumov, KhM. 2009. Antibiot Khimioter. 54: 44-52. PMID: 20583567
- Plasma membrane sterol complexation, generated by filipin, triggers signaling responses in tobacco cells. | Bonneau, L., et al. 2010. Biochim Biophys Acta. 1798: 2150-9. PMID: 20674542
- Analysis of cholesterol trafficking with fluorescent probes. | Maxfield, FR. and Wüstner, D. 2012. Methods Cell Biol. 108: 367-93. PMID: 22325611
- Membrane activity of the pentaene macrolide didehydroroflamycoin in model lipid bilayers. | Koukalová, A., et al. 2015. Biochim Biophys Acta. 1848: 444-52. PMID: 25450349
- Functional analysis of filipin tailoring genes from Streptomyces filipinensis reveals alternative routes in filipin III biosynthesis and yields bioactive derivatives. | Payero, TD., et al. 2015. Microb Cell Fact. 14: 114. PMID: 26246267
- Intracellular and Plasma Membrane Cholesterol Labeling and Quantification Using Filipin and GFP-D4. | Wilhelm, LP., et al. 2019. Methods Mol Biol. 1949: 137-152. PMID: 30790254
- Filipin-sterol complexes in the plasma membrane of zebrafish spermatozoa. | Kessel, RG., et al. 1985. Anat Rec. 212: 358-63. PMID: 4073552
- Filipin-cholesterol complexes form in uncoated vesicle membrane derived from coated vesicles during receptor-mediated endocytosis of low density lipoprotein. | McGookey, DJ., et al. 1983. J Cell Biol. 96: 1273-8. PMID: 6132922
- Detection of microdomains in biomembranes. An appraisal of recent developments in freeze-fracture cytochemistry. | Severs, NJ. and Robenek, H. 1983. Biochim Biophys Acta. 737: 373-408. PMID: 6349687
- The use and abuse of filipin to localize cholesterol in membranes. | Miller, RG. 1984. Cell Biol Int Rep. 8: 519-35. PMID: 6378397
Inhibitor of:
2810008M24Rik, 4930538K18Rik, 4932438H23Rik, 5430405G05Rik, 6430628N08Rik, 8D6, AP1S2, apoF, ATP9A, C18orf45, C8orf40, caveolin-1, caveolin-2, CCDC132, CCDC55, CCDC91, CCDC93, CD1B, Cd1d1, CD1E, Cdc50A, CHMP6, CL-P1, Clathrin LCA, Clathrin LCB, claudin-15, DSCR 5, EG666955, ENSMUSG00000056133, FAM126B, FCHO2, GLIPR1L1, Glycophorin D, GM2-AP, Gm364, Gm889, GML, GPAA1, hole, Hrs-2, IFITM5, KIAA1826_8430410K20Rik, LAMP-5, LDLRAD4, LIMP III, LOC643008, LRP11, MAMDC4, MANSC4, MBOAT2, MENTHO, MFSD6, NEEP21, Olfr1076, OR2AT4, ORP-6, Paralemmin 3, PCDH19, Peroxin 16, PIG-O, PRP2, Raftlin-2, SCARA5, SEC14L1, SEC14L5, Sec4, Seipin, SERINC1, Shigatoxin, SID-1, SMAGP, SNAP 23, SPFH1, SR-α, StARD6, SUSD3, taperin, THEM92, TM4SF4, TM6SF1, TMEM118, TMEM131, TMEM150B, TMEM156, TMEM168, TMEM177, Tmem210, TMEM215, TMEM220, TMEM233, TMEM31, TMEM34, TMEM41B, TMEM52, TMEM86A, TMEM87A, TMEM93, TMEM95, TMEM99, TMEM9B, TSPAN11, TSPAN3, TSPAN7, UHRF1BP1, UNC93A, UNQ830, UPIIIb, VAP-B/C, Vmn2r3, and VPS26B.Activator of:
AP-2σ1, CLTCL1, COTE1, DC-SIGN_CD209a, epsin 4, FIBCD1, MLN64, Mumps, MVB12B, NECAP 1, OS4, PGAP1, PIG-K, PIG-L, PRA1, Rab GDI β, SNX17, SNX32, SNX8, TGE Virus, TM7SF3, TMED9, and TMEM45B.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Filipin III, 500 µg | sc-205323 | 500 µg | $116.00 | |||
Filipin III, 1 mg | sc-205323A | 1 mg | $145.00 |