Filipin II
目录号 : GC43664An active component of the filipin complex
Cas No.:38620-77-8
Sample solution is provided at 25 µL, 10mM.
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- Purity: >95.00%
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- Datasheet
Filipin II is a polyene and an active component of the polyene antibiotic filipin complex . [1] It has broad-spectrum antifungal activity, reducing growth of various fungi, including B. dermatitidis, C. neoformans, and H. capsulatum (MICs = 1-10 μg/ml). Filipin II inhibits ADP-stimulated respiration in rat liver mitochondria when used at a concentration of 3.5 mg/ml. [2] It also induces hemolysis of liposomes in a cholesterol-independent manner (IC50 = 0.5 μg/ml).[3]
Reference:
[1]. Bergy, M.E., and Eble, T.E. The filipin complex. Biochemistry 7(2), 653-659 (1968).
[2]. Balcavage, W.X., Beale, M., Chasen, B., et al. Effect of filipin on rat-liver and yeast mitochondria. Biochim. Biophys. Acta. 162(4), 525-532 (1968).
[3]. Sessa, G., and Weissmann, G. Effects of four components of the polyene antibiotic, filipin, on phospholipid spherules (liposomes) and erythrocytes. J. Biol. Chem. 243(16), 4364-4371 (1968).
Cas No. | 38620-77-8 | SDF | |
化学名 | 4S,6S,8S,10R,12R,14R,16S,27S-octahydroxy-3R-hexyl-17,28R-dimethyl-oxacyclooctacosa-17E,19E,21E,23E,25E-pentaen-2-one | ||
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@H](CCCCCC)[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 | ||
分子式 | C35H58O10 | 分子量 | 638.8 |
溶解度 | Soluble in DMSO, DMF, Ethanol, Methanol | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 1.5654 mL | 7.8272 mL | 15.6544 mL |
5 mM | 0.3131 mL | 1.5654 mL | 3.1309 mL |
10 mM | 0.1565 mL | 0.7827 mL | 1.5654 mL |
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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.PMID:26246267DOI:10.1186/s12934-015-0307-4.
Background: Streptomyces filipinensis is the industrial producer of filipin, a pentaene macrolide, archetype of non-glycosylated polyenes, and widely used for the detection and the quantitation of cholesterol in biological membranes and as a tool for the diagnosis of Niemann-Pick type C disease. Genetic manipulations of polyene biosynthetic pathways have proven useful for the discovery of products with improved properties. Here, we describe the late biosynthetic steps for filipin III biosynthesis and strategies for the generation of bioactive filipin III derivatives at high yield. Results: A region of 13,778 base pairs of DNA from the S. filipinensis genome was isolated, sequenced, and characterized. Nine complete genes and two truncated ORFs were located. Disruption of genes proved that this genomic region is part of the biosynthetic cluster for the 28-membered ring of the polyene macrolide filipin. This set of genes includes two cytochrome P450 monooxygenase encoding genes, filC and filD, which are proposed to catalyse specific hydroxylations of the macrolide ring at C26 and C1' respectively. Gene deletion and complementation experiments provided evidence for their role during filipin III biosynthesis. Filipin III derivatives were accumulated by the recombinant mutants at high yield. These have been characterized by mass spectrometry and nuclear magnetic resonance following high-performance liquid chromatography purification thus revealing the post-polyketide steps during polyene biosynthesis. Two alternative routes lead to the formation of filipin III from the initial product of polyketide synthase chain assembly and cyclization filipin I, one trough Filipin II, and the other one trough 1'-hydroxyfilipin I, all filipin III intermediates being biologically active. Moreover, minimal inhibitory concentration values against Candida utilis and Saccharomyces cerevisiae were obtained for all filipin derivatives, finding that 1'-hydroxyfilipin and especially Filipin II show remarkably enhanced antifungal bioactivity. Complete nuclear magnetic resonance assignments have been obtained for the first time for 1'-hydroxyfilipin I. Conclusions: This report reveals the existence of two alternative routes for filipin III formation and opens new possibilities for the generation of biologically active filipin derivatives at high yield and with improved properties.