Filipin III
Filipin is the collective name given to four isomeric polyene macrolides isolated from cultures of S. filipinensis; Filipin III is the predominant isomer and the one used in most studies. Filipin binds to cholesterol in membranes, forming ultrastructural aggregates and complexes which can be visualized by freeze-fracture electron microscopy [1,2]. The binding of cholesterol also decreases the intrinsic fluorescence of Filipin, and this property has also been used to detect cholesterol in membrane fractions [3].
References:
[1]. Castanho M A R B, Coutinho A, Prieto M J E. Absorption and Fluorescence Spectra of Polyene Antibiotics in the Presence of Cholesterol. Journal of Biological Chemistry, 1992, 267(1): 204-209.
[2]. MILLER, R. The use and abuse of filipin to localize cholesterol in membranes. Cell Biology International Reports, 1984, 8(7): 519-535.
[3]. Nicholas J. Severs, Horst Robenek. Detection of microdomains in biomembranes An appraisal of recent developments in freeze-fracture cytochemistry. Biochim Biophys Acta, 1983,737(3-4):373-408.
- 1. René Rasche, Björn Udo Klink, et al. "Structure and mechanism of the RalGAP tumor suppressor complex." bioRxiv. November 25, 2024.
- 2. Kai Thoris, Miguel Correa Marrero, et al. "Uncoupling FRUITFULL's functions through modification of a protein motif identified by co-ortholog analysis." Nucleic Acids Res. 2024 Oct 30:gkae963. PMID: 39475190
- 3. Xijun Zhu, Woong Sub Byun, et al. "Activating p53Y220C with a Mutant-Specific Small Molecule." bioRxiv. October 28, 2024.
- 4. Zhewen Dong, Xiaofei She, et al. "The E3 ligase NEDD4L prevents colorectal cancer liver metastasis via degradation of PRMT5 to inhibit the AKT/mTOR signaling pathway." bioRxiv. October 24, 2024.
- 5. Irina S Abaeva, Alexander G Bulakhov, et al. "The ribosome-associated quality control factor TCF25 imposes K48 specificity on Listerin-mediated ubiquitination of nascent chains by binding and specifically orienting the acceptor ubiquitin." bioRxiv. 2024 Oct 18:2024.10.17.618946. PMID: 39464025
- 6. Casey Elizabeth Hudman-Wing, Ho Yee Joyce Fung, et al. "Allosteric degraders induce CRL5ASB8 mediated degradation of XPO1." bioRxiv. 2024 Oct 11:2024.10.07.617049. PMID: 39416201
- 7. Zhe Zhuang, Woong Sub Byun, et al. "Discovery of electrophilic degraders that exploit SNAr chemistry." bioRxiv. 2024 Sep 27:2024.09.25.615094. PMID: 39386645
- 8. Ria S Peesapati, Brianna L Austin-Byler, et al. "A specific folate activates serotonergic neurons to control C. elegans behavior." Nat Commun. 2024 Sep 30;15(1):8471. PMID: 39349491
- 9. Zi-Wei Chen, Satyanarayana M Chintala, et al. "Three classes of propofol binding sites on GABAA receptors." J Biol Chem. 2024 Sep 11:107778. PMID: 39270821
- 10. Amanda DiGuilio, Ben Cheng, et al. "The prolyl isomerase FKBP11 is a secretory translocon accessory factor." Mol Biol Cell. 2024 Nov 1;35(11):ar135 PMID: 39259761
- 11. T. Winkelmolen, P. Colleoni, et al. "VRS5 (HvTB1) binds to the promoter of tillering and floral homeotic genes to regulate their expression." bioRxiv 23 August 2024 Biology, Environmental Science.
- 12. Alireza Ghanbarpour, Bertina Telusma, et al. "An asymmetric nautilus-like HflK/C assembly controls FtsH proteolysis of membrane proteins." bioRxiv. 2024 Aug 10:2024.08.09.604662. PMID: 39149393
- 13. Samantha F Sedor, Sichen Shao, et al. "Mechanism of ASF1 Inhibition by CDAN1." bioRxiv. 2024 Aug 8:2024.08.08.607204. PMID: 39149339
- 14. Liuke Sun, Xing Guo, et al. "Human ANP32A/B are SUMOylated and utilized by avian influenza virus NS2 protein to overcome species-specific restriction." bioRxiv 20 July 2024
- 15. Joan Onwunma, Saeed Binsabaan, et al. "The structural and biophysical basis of substrate binding to the hydrophobic groove in Ubiquilin Sti1 domains." bioRxiv. 2024 Jul 10:2024.07.10.602902. PMID: 39026758
- 16. Yan Li, Yuxiang Lin, et al. "MAZ-mediated up-regulation of BCKDK reprograms glucose metabolism and promotes growth by regulating glucose-6-phosphate dehydrogenase stability in triple-negative breast cancer." Cell Death Dis. 2024 Jul 18;15(7):516 PMID: 39025830
- 17. Ashley Scheutzow, Sachini Thanthirige, et al. "E3 ligase recruitment by UBQLN2 protects substrates from proteasomal degradation." bioRxiv. July 04, 2024.
- 18. Siddhi Omkar, Courtney Shrader, et al. "Acetylation of the yeast Hsp40 chaperone protein Ydj1 fine-tunes proteostasis and translational fidelity." bioRxiv. 2024 Jun 13:2024.06.13.598777. PMID: 38915721
- 19. Merijn Kerstens, Carla Galinha, et al. "PLETHORA transcription factors promote early embryo development through induction of meristematic potential." Development. 2024 Jun 15;151(12):dev202527. PMID: 38884589
| Physical Appearance | A crystalline solid |
| Storage | Store at -20°C, protect from light. This product is unstable in solution. It is recommended to avoid light and store it separately to avoid repeated freeze-thaw cycles. Use it as soon as possible |
| M.Wt | 654.83 |
| Cas No. | 480-49-9 |
| Formula | C35H58O11 |
| Solubility | Soluble in DMSO |
| Chemical Name | (3R,4S,6S,8S,10R,12R,14R,16S,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,16,27-octahydroxy-3-((R)-1-hydroxyhexyl)-17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one |
| SDF | Download SDF |
| Canonical 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 |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment [1]: | |
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Cell lines |
ergosterol-containing ciliary membranes |
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Preparation method |
This compound is soluble in DMSO. General tips for obtaining a higher concentration: Please warm the tube at 37°C for 10 minutes and/or shake it in the ultrasonic bath for a while. |
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Reacting condition |
12.7 μM |
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Applications |
Filipin induced lysis of lecithin-cholesterol and lecithin-ergosterol vesicles, but did not lyse vesicles prepared from lecithin alone and from mixtures of lecithin and epicholesterol, thiocholesterol, androstan-3/3-ol, or cholestanol. Filipin treatment of ergosterol-containing ciliary membranes produced annuli with mean diameter almost identical with that in filipin-treated lecithin-ergosterol vesicles. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: [1]. Bittman R, Chen W C, Anderson O R. Interaction of filipin III and amphotericin B with lecithin-sterol vesicles and cellular membranes. Spectral and electron microscope studies[J]. Biochemistry, 1974, 13(7): 1364-1373. |
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Quality Control & MSDS
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Purity = 98.00%
- COA (Certificate Of Analysis)
- MSDS (Material Safety Data Sheet)
- Datasheet
Chemical structure
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