Delivery of fluorescent-labeled cyclodextrin by liposomes: role of transferrin modification and phosphatidylcholine composition

Abstract

Drug-in-CD-in-liposome (DCL) systems which encapsulate the drug/CD inclusion complexes into inner aqueous phase of liposomes have been applied as a novel strategy to improve efficacy of lipophilic antitumor drugs. The aim of this work was to assess the role of transferrin (Tf) modification and phosphatidylcholine (PC) composition on the properties of liposomes containing hydroxypropyl-β-cyclodextrin (HP-β-CD). Fluorescence dye, FITC, was conjugated with HP-β-CD to facilitate the analysis. The resulting FITC-HP-β-CD was further encapsulated into liposomes and then the liposomes were modified with Tf. The FITC-HP-β-CD-loaded liposomes with different PC compositions were compared in terms of particle size, zeta potential, FITC content, FITC-HP-β-CD leakage, phase transition temperature (T) and cellular uptake. The apparent partition coefficient values of different PCs were also determined. Compared to PEGylated liposomes, FITC-HP-β-CD-loaded liposomes modified with Tf had been proved to significantly increase vesicle stability and specific cellular uptake. Moreover, PC composition affected the properties of liposomes. Soybean phosphatidylcholine (SPC) liposomes modified with Tf were found to be more easily internalized into tumor cells than 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine (DPPC) and hydrogenated soybean phosphatidylcholine (HSPC) while Tf density on the liposomal surface was similar. And the lipophilicity of SPC was found to be much higher than DPPC and HSPC. Collectively, by the optimization of PC composition, the development of DCL modified with Tf might represent a potential strategy for the antitumor application of lipophilic drugs.

Chemosensitization of Temozolomide-Resistant Pediatric Diffuse Midline Glioma Using Potent Nanoencapsulated Forms of a N(3)-Propargyl Analogue

“…A fluorescein isothiocyanate (FITC)labeled solution of SBE-β-CD was prepared as described previously with some modifications. 32 Briefly, 3.8 mg of FITC (Thermo Fisher Scientific, USA) in 200 μL of DMSO was introduced dropwise into 2 mL of 0.75% SBE-β-CD in sodium hydroxide (0.1 M, pH 10.5). The mixture was magnetically stirred at RT for 24 h in the dark.…”

Supramolecular Dissolving Microneedle Patch Loading Hydrophobic Glucocorticoid for Effective Psoriasis Treatment

“…Visualization of TA Permeation into the Skin. To visualize the TAMN-assisted TA permeation into the skin, HPCD was labeled with FITC according to a previous report, 40 and the green fluorescence was characterized by a confocal laser scanning microscope (CLSM, Olympus FV1200, Japan). Briefly, psoriatic mouse skin was placed on an object slide, and then TAMN (labeled with FITC) was inserted into the skin surface for 2 min.…”

Designing of a β‐Cyclodextrin‐based supramolecular fluorescent sensor doped with superparamagnetic α‐Fe2O3 nanoparticles with improved light fastness, thermal, and photoluminescent properties

“…CD modified with an azo benzene derivative was developed as a novel photo-switchable host to regulate molecular function in the supramolecular system. 19 Fluorescently modified hydroxypropyl-CD was synthesized and their delivery by liposomes was monitored by Chen et al 20 A selective fluorescent pattern to sense and distinguish proteins on the basis of dissociation of aqueous polymerpyrene/γ-cyclodextrin (γ-CD) inclusion complexes was developed. 21 1-Pyrene butyric acid (PBA), a well-studied fluoroprobe has been both covalently and non-covalently bonded to different macromolecular and supramolecular systems.…”