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BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

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    0476521 - UEB-Q 2018 RIV DE eng J - Journal Article
    Škorpilová, Ludmila - Rimpelová, S. - Jurášek, M. - Buděšínský, Miloš - Lokajová, Jana - Effenberg, R. - Slepička, P. - Ruml, T. - Kmoníčková, Eva - Drašar, P. B. - Wimmer, Zdeněk
    BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide.
    Beilstein Journal of Organic Chemistry. Roč. 13, JUL 4 (2017), s. 1316-1324. ISSN 1860-5397
    R&D Projects: GA MŠk LD15012; GA MŠk(CZ) LO1304
    Institutional support: RVO:61389030 ; RVO:61388963 ; RVO:68378041
    Keywords : BODIPY conjugates * Cancer targeting * Drug delivery * Liposomes * Natural compounds * Sesquiterpene lactone trilobolide
    Subject RIV: CC - Organic Chemistry; FR - Pharmacology ; Medidal Chemistry (UEM-P)
    OBOR OECD: Organic chemistry; Pharmacology and pharmacy (UEM-P)
    Impact factor: 2.330, year: 2017

    Like thapsigargin, which is undergoing clinical trials, trilobolide is a natural product with promising anticancer and anti-inflammatory properties. Similar to thapsigargin, it has limited aqueous solubility that strongly reduces its potential medicinal applications. The targeted delivery of hydrophobic drugs can be achieved using liposome-based carriers. Therefore, we designed a traceable liposomal drug delivery system for trilobolide. The fluorescent green-emitting dye BODIPY, cholesterol and trilobolide were used to create construct 6. The liposomes were composed of dipalmitoyl-3-trimethylammoniumpropane and phosphatidylethanolamine. The whole system was characterized by atomic force microscopy, the average size of the liposomes was 150 nm in width and 30 nm in height. We evaluated the biological activity of construct 6 and its liposomal formulation, both of which showed immunomodulatory properties in primary rat macrophages. The uptake and intracellular distribution of construct 6 and its liposomal formulation was monitored by means of live-cell fluorescence microscopy in two cancer cell lines. The encapsulation of construct 6 into the liposomes improved the drug distribution in cancer cells and was followed by cell death. This new liposomal trilobolide derivative not only retains the biological properties of pure trilobolide, but also enhances the bioavailability, and thus has potential for the use in theranostic applications.
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