Filipin III

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Filipin III

2023-10-16 08:03| 来源: 网络整理| 查看: 265

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.

参考文献

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: 11342153Permeabilizing action of filipin III on model membranes through a filipin-phospholipid binding.  |  Milhaud, J. 1992. Biochim Biophys Acta. 1105: 307-18. PMID: 1375101Filipin orientation revealed by linear dichroism. Implication for a model of action.  |  Lopes, SC., et al. 2004. J Am Chem Soc. 126: 5396-402. PMID: 15113211Absorption and fluorescence spectra of polyene antibiotics in the presence of cholesterol.  |  Castanho, MA., et al. 1992. J Biol Chem. 267: 204-9. PMID: 1730589Inhibition 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: 20583567Plasma membrane sterol complexation, generated by filipin, triggers signaling responses in tobacco cells.  |  Bonneau, L., et al. 2010. Biochim Biophys Acta. 1798: 2150-9. PMID: 20674542Analysis of cholesterol trafficking with fluorescent probes.  |  Maxfield, FR. and Wüstner, D. 2012. Methods Cell Biol. 108: 367-93. PMID: 22325611Membrane activity of the pentaene macrolide didehydroroflamycoin in model lipid bilayers.  |  Koukalová, A., et al. 2015. Biochim Biophys Acta. 1848: 444-52. PMID: 25450349Functional 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: 26246267Intracellular and Plasma Membrane Cholesterol Labeling and Quantification Using Filipin and GFP-D4.  |  Wilhelm, LP., et al. 2019. Methods Mol Biol. 1949: 137-152. PMID: 30790254Filipin-sterol complexes in the plasma membrane of zebrafish spermatozoa.  |  Kessel, RG., et al. 1985. Anat Rec. 212: 358-63. PMID: 4073552Filipin-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: 6132922Detection 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: 6349687The use and abuse of filipin to localize cholesterol in membranes.  |  Miller, RG. 1984. Cell Biol Int Rep. 8: 519-35. PMID: 6378397


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