Filipin | CAS#480-49-9 | antibiotic

Filipin
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 585298

CAS#: 480-49-9

Description: Filipin is a complex of polyene antibiotics obtained from Streptomyces filipinensis.

Chemical Structure

Filipin

CAS# 480-49-9

Instruction

Theoretical Analysis

MedKoo Cat#: 585298
Name: Filipin
CAS#: 480-49-9
Chemical Formula: C35H58O11
Exact Mass: 654.40
Molecular Weight: 654.840
Elemental Analysis: C, 64.20; H, 8.93; O, 26.88

Price and Availability

Size	Price	Availability
1mg	USD 340	2 Weeks
5mg	USD 940	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Filipin; U 5956; U-5956; U5956

IUPAC/Chemical Name: (17E,19E,21E,23E,25E)-4,6,8,10,12,14,16,27-octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one

InChi Key: IMQSIXYSKPIGPD-ZPXVTHDFSA-N

InChi Code: 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+

SMILES Code: O=C1OC(C)C(O)/C=C/C=C/C=C/C=C/C=C(C)/C(O)CC(O)CC(O)CC(O)CC(O)CC(O)CC(O)C1C(O)CCCCC

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	5.0	7.64
	DMSO	10.0	15.27
	Ethanol	2.0	3.05

Preparing Stock Solutions

The following data is based on the product molecular weight 654.84 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Vanier MT, Latour P. Laboratory diagnosis of Niemann-Pick disease type C: the filipin staining test. Methods Cell Biol. 2015;126:357-75. doi: 10.1016/bs.mcb.2014.10.028. Epub 2015 Jan 14. PubMed PMID: 25665455.

2: Payero TD, Vicente CM, Rumbero Á, Barreales EG, Santos-Aberturas J, de Pedro A, Aparicio JF. Functional analysis of filipin tailoring genes from Streptomyces filipinensis reveals alternative routes in filipin III biosynthesis and yields bioactive derivatives. Microb Cell Fact. 2015 Aug 7;14:114. doi: 10.1186/s12934-015-0307-4. PubMed PMID: 26246267; PubMed Central PMCID: PMC4527110.

3: Wilhelm LP, Voilquin L, Kobayashi T, Tomasetto C, Alpy F. Intracellular and Plasma Membrane Cholesterol Labeling and Quantification Using Filipin and GFP-D4. Methods Mol Biol. 2019;1949:137-152. doi: 10.1007/978-1-4939-9136-5_11. PubMed PMID: 30790254.

4: Milhaud J. Permeabilizing action of filipin III on model membranes through a filipin-phospholipid binding. Biochim Biophys Acta. 1992 Apr 13;1105(2):307-18. PubMed PMID: 1375101.

5: Koukalová A, Pokorná Š, Fišer R, Kopecký V Jr, Humpolíčková J, Černý J, Hof M. Membrane activity of the pentaene macrolide didehydroroflamycoin in model lipid bilayers. Biochim Biophys Acta. 2015 Feb;1848(2):444-52. doi: 10.1016/j.bbamem.2014.10.038. Epub 2014 Nov 4. PubMed PMID: 25450349.

6: Loura LM, Castanho MA, Fedorov A, Prieto M. A photophysical study of the polyene antibiotic filipin. Self-aggregation and filipin--ergosterol interaction. Biochim Biophys Acta. 2001 Feb 9;1510(1-2):125-35. PubMed PMID: 11342153.

7: McGookey DJ, Fagerberg K, Anderson RG. Filipin-cholesterol complexes form in uncoated vesicle membrane derived from coated vesicles during receptor-mediated endocytosis of low density lipoprotein. J Cell Biol. 1983 May;96(5):1273-8. PubMed PMID: 6132922; PubMed Central PMCID: PMC2112663.

8: Maxfield FR, Wüstner D. Analysis of cholesterol trafficking with fluorescent probes. Methods Cell Biol. 2012;108:367-93. doi: 10.1016/B978-0-12-386487-1.00017-1. PubMed PMID: 22325611; PubMed Central PMCID: PMC3626500.

9: Samedova AA, Kasumov KhM. [Mechanism of action of macrolide antibiotic filipin on cell and lipid membranes]. Antibiot Khimioter. 2009;54(11-12):44-52. Review. Russian. PubMed PMID: 20583567.

10: Kessel RG, Tung HN, Roberts R. Filipin-sterol complexes in the plasma membrane of zebrafish spermatozoa. Anat Rec. 1985 Aug;212(4):358-63. PubMed PMID: 4073552.

11: Duindam HJ, Vrensen GF, Otto C, Puppels GJ, Greve J. New approach to assess the cholesterol distribution in the eye lens: confocal Raman microspectroscopy and filipin cytochemistry. J Lipid Res. 1995 May;36(5):1139-46. PubMed PMID: 7658162.

12: Lopes SC, Goormaghtigh E, Cabral BJ, Castanho MA. Filipin orientation revealed by linear dichroism. Implication for a model of action. J Am Chem Soc. 2004 May 5;126(17):5396-402. PubMed PMID: 15113211.

13: Rintoul DA, Neungton N, Silbert DF. Isolation and characterization of filipin-resistant LM cell variants not auxotrophic for sterol. J Lipid Res. 1982 Mar;23(3):405-9. PubMed PMID: 7077154.

14: Rejman J, Bragonzi A, Conese M. Role of clathrin- and caveolae-mediated endocytosis in gene transfer mediated by lipo- and polyplexes. Mol Ther. 2005 Sep;12(3):468-74. PubMed PMID: 15963763.

15: Sekiya T, Takenawa T, Nozawa Y. Reorganization of membrane cholesterol during membrane fusion in myogenesis in vitro: a study using the filipin-cholesterol complex. Cell Struct Funct. 1984 Jun;9(2):143-55. PubMed PMID: 6498947.

16: Boutté Y, Men S, Grebe M. Fluorescent in situ visualization of sterols in Arabidopsis roots. Nat Protoc. 2011 Apr;6(4):446-56. doi: 10.1038/nprot.2011.323. Epub 2011 Mar 18. PubMed PMID: 21412273.

17: Orci L, Miller RG, Montesano R, Perrelet A, Amherdt M, Vassalli P. Opposite polarity of filipin-induced deformations in the membrane of condensing vacuoles and zymogen granules. Science. 1980 Nov 28;210(4473):1019-21. PubMed PMID: 7434010.

18: Brajtburg J, Medoff G, Kobayashi GS, Elberg S. Influence of extracellular K+ or Mg2+ on the stages of the antifungal effects of amphotericin B and filipin. Antimicrob Agents Chemother. 1980 Oct;18(4):593-7. PubMed PMID: 7004343; PubMed Central PMCID: PMC284055.

19: Sigismund S, Argenzio E, Tosoni D, Cavallaro E, Polo S, Di Fiore PP. Clathrin-mediated internalization is essential for sustained EGFR signaling but dispensable for degradation. Dev Cell. 2008 Aug;15(2):209-19. doi: 10.1016/j.devcel.2008.06.012. PubMed PMID: 18694561.

20: Simons HL, Severs NJ. Plasmalemmal vesicles and the effects of sterol-binding agents in rabbit aortic endothelium. J Cell Sci. 1986 Jul;83:141-53. PubMed PMID: 3805137.

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