Filipin III A cholesterol-binding, fluorescing antibiotic

Filipin III (CAS 480-49-9)

Filipin III | CAS 480-49-9 is rated 5.0 out of 5 by 1.
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Synonym: 16,20,22,24-Octacosapentenoic acid, 3,5,7,9,11,13,15,26,27-nonahydroxy-2-(1-hydroxyhexyl)-16-methyl-, 27-lactone
Application: A cholesterol-binding, fluorescing antibiotic
CAS Number: 480-49-9
Purity: >85%
Molecular Weight: 654.83
Molecular Formula: C35H58O11
* Refer to Certificate of Analysis for lot specific data (including water content).
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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. The compound has also been used in tobacco cells and observed to activate ligand-independent signaling responses. Through Filipin III's cholesterol sequestering activity, the compound was able to disrupt the lipid rafts in both normal and transformed keratinocytes resulting in inhibition of the AKT pathway.


References

1. Severs, N.J., et al. 1983. Biochim. Biophys. Acta. 737: 373-408. PMID: 6349687
2. Miller, R.G. 1984. Cell Biol. Int. Rep. 8: 519-535. PMID: 6378397
3. Castanho, M.A., et al. 1992. J. Biol. Chem. 267: 204-209. PMID: 1730589
4. Bonneau, L., et al. 2010. Biochim. Biophys. Acta. 1798: 2150-2159. PMID: 20674542
5. Calay, D., et al. 2010. J. Invest. Dermatol. 130: 1136-1145. PMID: 20054340

Physical State :
Solid
Storage :
Store at -20° C
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
76959072
SMILES :
CCCCC[C@H](C1[C@H](C[C@H](C[C@H](C[C@H](C[C@H](C[C@H](C[C@@H](/C(=C\\C=C\\C=C\\C=C\\C=C\\[C@@H]([C@H](OC1=O)C)O)/C)O)O)O)O)O)O)O)O

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Filipin III  Product Citations

See how others have used Filipin III. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 28223798  Gao, W. et al. 2017. Int J Nanomedicine. 12: 1047-1064.

PMID: # 26156035  Guo, T. et al. 2015. J Nanobiotechnology. 13: 47.

Citations 1 to 2 of 2 total

How should the chemical be stored after dissolving in DMSO?

Asked by: chemicalsmg
Thank you for your question. Filipin III: sc-205323 should not be stored as a solution for a long period of time. After dissolving in DMSO, it should be used within 24 hours of dissolving or it may result in reduced activity.
Answered by: Chemical Support 3
Date published: 2018-05-10

What is this soluble in?

Asked by: chemicalsmg
Thank you for your question. Filipin III: sc-205323 is soluble in methanol at 10 mg/ml.
Answered by: Chemical Support 3
Date published: 2017-03-09
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Rated 5 out of 5 by from Calay et al Calay et al. (PubMed ID 20054340) used Filipin III for lipid raft disruption in normal human keratinocytes and precancerous or transformed keratinocytes, which abrogated the binding of Akt. -SCBT Publication Review
Date published: 2015-06-30
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