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Öğe Thiolated ?-cyclodextrin: The likely smallest drug carrier providing enhanced cellular uptake and endosomal escape(Elsevier Sci Ltd, 2023) Kaplan, Ozlem; Truszkowska, Martyna; Kali, Gergely; Knoll, Patrick; Massani, Mariana Blanco; Braun, Doris Elfriede; Bernkop-Schnuerch, AndreasThis study aimed to evaluate the effect of thiolated & alpha;-cyclodextrin (& alpha;-CD-SH) on the cellular uptake of its payload.For this purpose, & alpha;-CD was thiolated using phosphorous pentasulfide. Thiolated & alpha;-CD was characterized by FT -IR and 1H NMR spectroscopy, differential scanning calorimetry (DSC), and powder X-ray diffractometry (PXRD). Cytotoxicity of & alpha;-CD-SH was evaluated on Caco-2, HEK 293, and MC3T3 cells. Dilauryl fluorescein (DLF) and coumarin-6 (Cou) serving as surrogates for a pharmaceutical payload were incorporated in & alpha;-CD-SH, and cellular uptake was analyzed by flow cytometry and confocal microscopy. Endosomal escape was investigated by confocal microscopy and hemolysis assay.Results showed no cytotoxic effect within 3 h, while dose-dependent cytotoxicity was observed within 24 h. The cellular uptake of DLF and Cou was up to 20-and 11-fold enhanced by & alpha;-CD-SH compared to native & alpha;-CD, respectively. Furthermore, & alpha;-CD-SH provided an endosomal escape.According to these results, & alpha;-CD-SH is a promising carrier to shuttle drugs into the cytoplasm of target cells.
