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Filipin Complex

A neutral polyene with antifungal activity

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  • 货号: ajci21054
  • CAS: 11078-21-0
  • 别名: 菲律宾菌素复合体
  • 分子式: C35H58O11 (for Filipin III)
  • 分子量: 654.8
  • 纯度: >98%
  • 溶解度: DMF: Soluble,DMSO: Soluble,Ethanol: Soluble,Methanol: Soluble
  • 储存: Store at -20°C,protect from light
  • 库存: 现货

Background

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]


参考文献:
[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.

Protocol

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.

参考文献:

[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.

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