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Filipin Complex Sale

(Synonyms: 菲律宾菌素复合体) 目录号 : GC18406

A neutral polyene with antifungal activity

Filipin Complex Chemical Structure

Cas No.:11078-21-0

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10mM (in 1mL DMSO)
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1mg
¥395.00
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5mg
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50mg
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Sample solution is provided at 25 µL, 10mM.

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实验参考方法

Cell experiment [1]:

Cell lines

CHSE-214 cells

Preparation Method

Control HeLa cells were pre-incubated for 1 h with 0 or 5 µg/ml Filipin Complex and Alexa Fluor 594-conjugated cholera toxin B (CTB-A594) subunit were added. After 30 min, cells were processed for confocal fluorescence microscopy.

Reaction Conditions

0 or 5 µg/ml Filipin Complex for 1 h

Applications

It shows the effect of Filipin Complex on IPNV infection. No effect on viral infection was observed.

References:

[1]. Levican J, Miranda-CÁrdenas C, Soto-Rifo R, Aguayo F, Gaggero A, LeÓn O. Infectious pancreatic necrosis virus enters CHSE-214 cells via macropinocytosis. Sci Rep. 2017 Jun 8;7(1):3068. doi: 10.1038/s41598-017-03036-w. PMID: 28596575; PMCID: PMC5465193.

产品描述

Filipin complex is a neutral polyene,it has antifungal activity.As a fluorescent compound, Filipin complex can be used for sterol imaging in labeled biological structures,Excitation/emission values of the complexes were 338/480 nm[1,4] . Filipin III is the main component of Filipin complex which is composed of four parts[3] . The interaction of Filipin Complex with steroids was found to be related both to the functional group at the 3-position and the aliphatic chain of the steroid[7] .

Cells were pretreated with 1 and 5 g/mL of Filipin Complex for 1 h and infected with IPNV at a MOI of 1 for 1 h. After 12 h of incubation in the presence of the drug, IPNV VP2/VP3 expression was revealed by immunofluorescence. It shows the effect of Filipin Complex on IPNV infection. No effect on viral infection was observed[2] . The Filipin Complex complex can bind various sterols in aqueous solutions and fungal cell membranes, especially 24α-methyl cholesterol, 24α-ethyl cholesterol, and cholesterol, inducing membrane pit formation and leakage of cell contents[5] . The Filipin Complex complex can inhibit cell growth and mitochondrial terminal electron transport in Saccharomyces cerevisiae[6] .

菲律宾配合物是一种中性多烯,具有抗真菌活性。作为一种荧光化合物,菲律宾配合物可用于标记生物结构中的甾醇成像,配合物的激发/发射值为338/480 nm[1 ,4] . Filipin III是Filipin复合体的主要成分,由四部分组成[3]。发现Filipin Complex与类固醇的相互作用与类固醇3-位官能团和脂肪链有关[7]

细胞用 1 和 5 g/mL 的菲律宾复合物预处理 1 小时,然后用 MOI 为 1 的 IPNV 感染 1 小时。在药物存在下孵育 12 小时后,通过免疫荧光显示 IPNV VP2/VP3 表达。它显示了 Filipin Complex 对 IPNV 感染的影响。未观察到对病毒感染的影响[2]。 Filipin Complex复合物可结合水溶液和真菌细胞膜中的多种甾醇,尤其是24α-甲基胆固醇、24α-乙基胆固醇和胆固醇,诱导膜凹坑形成和细胞内容物渗漏[5]。 Filipin Complex复合物可抑制酿酒酵母细胞生长和线粒体末端电子传递[6]

References:
[1]. Castanho MA, Coutinho A, et,al.Absorption and fluorescence spectra of polyene antibiotics in the presence of cholesterol. J Biol Chem. 1992 Jan 5;267(1):204-9. PMID: 1730589
[2]. Levican J, Miranda-Cárdenas C, et,al. Infectious pancreatic necrosis virus enters CHSE-214 cells via macropinocytosis. Sci Rep. 2017 Jun 8;7(1):3068. doi: 10.1038/s41598-017-03036-w. PMID: 28596575; PMCID: PMC5465193.
[3]. Payero TD, Vicente CM, et,al. 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. PMID: 26246267; PMCID: PMC4527110.
[4]. Kühnl A, Musiol A,et,al.Late Endosomal/Lysosomal Cholesterol Accumulation Is a Host Cell-Protective Mechanism Inhibiting Endosomal Escape of Influenza A Virus. mBio. 2018 Jul 24;9(4):e01345-18. doi: 10.1128/mBio.01345-18. PMID: 30042202; PMCID: PMC6058292.
[5]. Kitajima Y, Sekiya T,et,al. Freeze-fracture ultrastructural alterations induced by filipin, pimaricin, nystatin and amphotericin B in the plasmia membranes of Epidermophyton, Saccharomyces and red complex-induced membrane lesions. Biochim Biophys Acta. 1976 Dec 2;455(2):452-65. doi: 10.1016/0005-2736(76)90317-5. PMID: 793632.
[6]. SHAW PD, ALLAM AM,et,al. EFFECT OF FILIPIN ON THE TERMINAL ELECTRON TRANSPORT SYSTEM OF SACCHAROMYCES CEREVISIAE. Biochim Biophys Acta. 1964 Jul 8;89:33-41. doi: 10.1016/0926-6569(64)90098-7. PMID: 14213010.
[7]. Kleinschmidt MG, Chough KS. Effect of filipin on liposomes prepared with different types of steroids. Plant Physiol. 1972 May;49(5):852-6. doi: 10.1104/pp.49.5.852. PMID: 16658060; PMCID: PMC366064.

Chemical Properties

Cas No. 11078-21-0 SDF
别名 菲律宾菌素复合体
Canonical SMILES N/A
分子式 C35H58O11 (for Filipin III) 分子量 654.8
溶解度 DMF: Soluble,DMSO: Soluble,Ethanol: Soluble,Methanol: Soluble 储存条件 Store at -20°C,protect from light
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1 mM 1.5272 mL 7.6359 mL 15.2718 mL
5 mM 0.3054 mL 1.5272 mL 3.0544 mL
10 mM 0.1527 mL 0.7636 mL 1.5272 mL
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Research Update

The filipin complex

Separation of the filipin complex by gradient-elution high performance liquid chromatography

A method has been developed for the separation of the filipin complex components by gradient-elution high performance liquid chromatography (HPLC). The elution order for the major filipin components (filipins I approximately IV) was established by first isolating the component fractions by thin-layer chromatography. Each component fraction was then subjected to gradient HPLC. The order of elution for the major filipin components was from first to last: III, IV, II and I. The unexpected reversal in the elution order for filipins III and IV may be evidence that the two filipins are stereoisomeric at the C-1' position. Finally, gradient elution HPLC was used to compare various preparations of filipin. In addition, the technique has been applied to other preparations of polyene antibiotics which have structures similar to that of filipin.

Cholesterol reporter molecules

Cholesterol is a major constituent of the membranes in most eukaryotic cells where it fulfills multiple functions. Cholesterol regulates the physical state of the phospholipid bilayer, affects the activity of several membrane proteins, and is the precursor for steroid hormones and bile acids. Cholesterol plays a crucial role in the formation of membrane microdomains such as "lipid rafts" and caveolae. However, our current understanding on the membrane organization, intracellular distribution and trafficking of cholesterol is rather poor. This is mainly due to inherent difficulties to label and track this small lipid. In this review, we describe different approaches to detect cholesterol in vitro and in vivo. Cholesterol reporter molecules can be classified in two groups: cholesterol binding molecules and cholesterol analogues. The enzyme cholesterol oxidase is used for the determination of cholesterol in serum and food. Susceptibility to cholesterol oxidase can provide information about localization, transfer kinetics, or transbilayer distribution of cholesterol in membranes and cells. The polyene filipin forms a fluorescent complex with cholesterol and is commonly used to visualize the cellular distribution of free cholesterol. Perfringolysin O, a cholesterol binding cytolysin, selectively recognizes cholesterol-rich structures. Photoreactive cholesterol probes are appropriate tools to analyze or to identify cholesterol binding proteins. Among the fluorescent cholesterol analogues one can distinguish probes with intrinsic fluorescence (e.g., dehydroergosterol) from those possessing an attached fluorophore group. We summarize and critically discuss the features of the different cholesterol reporter molecules with a special focus on recent imaging approaches.

Fluorometric evidence for the binding of cholesterol to the filipin complex

Reorganization of membrane cholesterol during membrane fusion in myogenesis in vitro: a study using the filipin-cholesterol complex

Using filipin and freeze-fracture electron microscopy, we examined the distribution of membrane cholesterol during the fusion of myoblasts in vitro. The early stages of fusion were characterized by the depletion of cholesterol from the membrane apposition sites, at which the plasma membranes of two adjacent cells were in close contact. At first, filipin-cholesterol complexes were absent from the plasma membrane of one cell only and were distributed homogeneously on the membrane of the other cell. Eventually, both of the closely apposed membranes became almost completely free the filipin-cholesterol complexes. Membrane fusion took place at several points within the filipin-cholesterol complex-free areas. In later stages, the cytoplasms of the fusing cells became confluent by fenestration of the plasma membranes formed with the filipin-cholesterol complex-free regions. Our observations suggest that membrane cholesterol is reorganized at these fusion sites and that fusion initiated by the juxtaposition of the cholesterol-free areas of each plasma membrane of the adjacent cells.