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      Multifunctional supramolecular vesicles based on the complex of ferrocenecarboxylic acid capped pillar[5]arene and a galactose derivative for targeted drug delivery

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          Abstract

          Supramolecular vesicles have been constructed based on the host–guest complexation, which show dual-responsiveness and cancer cells targetability.

          Abstract

          Supramolecular vesicles based on the host–guest complexation of ferrocenecarboxylic acid capped pillar[5]arene and a galactose derivative have been constructed, which showed dual-responsiveness and cancer cells targetability resulting from its ferrocenecarboxylic acid units and galactose units, respectively. This work provides a good example for the construction of multifunctional nanocarriers for targeted drug delivery.

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          para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property.

          Tomoki Ogoshi, Suguru Kanai, Shuhei Fujinami … (2008)
          Condensation of 1,4-dimethoxybenzene (DMB) with paraformaldehyde in the presence of BF3.O(C2H5)2 gave novel para-bridged pentacyclic pillar DMB (DMpillar[5]arene). Moreover, para-bridged pentacyclic hydroquinone (pillar[5]arene) was prepared. Pillar[5]arene formed 1:1 host-guest complexes with dialkyl viologen and alkyl pyridinium derivatives. However, pillar[5]arene did not form complexes with the diadamantyl viologen derivative since a bulky adamantyl group was unable to thread the cavity of pillar[5]arene.
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            Efficient delivery of genome-editing proteins using bioreducible lipid nanoparticles.

            Ming Wang, John Zuris, Fantao Meng … (2016)
            A central challenge to the development of protein-based therapeutics is the inefficiency of delivery of protein cargo across the mammalian cell membrane, including escape from endosomes. Here we report that combining bioreducible lipid nanoparticles with negatively supercharged Cre recombinase or anionic Cas9:single-guide (sg)RNA complexes drives the electrostatic assembly of nanoparticles that mediate potent protein delivery and genome editing. These bioreducible lipids efficiently deliver protein cargo into cells, facilitate the escape of protein from endosomes in response to the reductive intracellular environment, and direct protein to its intracellular target sites. The delivery of supercharged Cre protein and Cas9:sgRNA complexed with bioreducible lipids into cultured human cells enables gene recombination and genome editing with efficiencies greater than 70%. In addition, we demonstrate that these lipids are effective for functional protein delivery into mouse brain for gene recombination in vivo. Therefore, the integration of this bioreducible lipid platform with protein engineering has the potential to advance the therapeutic relevance of protein-based genome editing.
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              pH-responsive supramolecular vesicles based on water-soluble pillar[6]arene and ferrocene derivative for drug delivery.

              Qunpeng Duan, Yu Cao, Yan-Yan Li … (2013)
              The drug delivery system based on supramolecular vesicles that were self-assembled by a novel host-guest inclusion complex between a water-soluble pillar[6]arene (WP6) and hydrophobic ferrocene derivative in water has been developed. The inclusion complexation between WP6 and ferrocene derivative in water was studied by (1)H NMR, UV-vis, and fluorescence spectroscopy, which showed a high binding constant of (1.27 ± 0.42) × 10(5) M(-1) with 1:1 binding stoichiometry. This resulting inclusion complex could self-assemble into supramolecular vesicles that displayed a significant pH-responsive behavior in aqueous solution, which were investigated by fluorescent probe technique, dynamic laser scattering, and transmission electron microscopy. Furthermore, the drug loading and in vitro drug release studies demonstrated that these supramolecular vesicles were able to encapsulate mitoxantrone (MTZ) to achieve MTZ-loaded vesicles, which particularly showed rapid MTZ release at low-pH environment. More importantly, the cellular uptake of these pH-responsive MTZ-loaded vesicles by cancer cells was observed by living cell imaging techniques, and their cytotoxicity assay indicated that unloaded vesicles had low toxicity to normal cells, which could dramatically reduce the toxicity of MTZ upon loading of MTZ. Meanwhile, MTZ-loaded vesicles exhibited comparable anticancer activity in vitro as free MTZ to cancer cells under examined conditions. This study suggests that such supramolecular vesicles have great potential as controlled drug delivery systems.
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                Author and article information

                Journal
                Journal ID (publisher-id): CHCOFS
                Title: Chemical Communications
                Abbreviated Title: Chem. Commun.
                Publisher: Royal Society of Chemistry (RSC)
                ISSN (Print): 1359-7345
                ISSN (Electronic): 1364-548X
                Publication date Created: 2016
                Publication date (Electronic): 2016
                Volume: 52
                Issue: 61
                Pages: 9578-9581
                Affiliations
                [1 ]Shaanxi Key Laboratory of Natural Products & Chemical Biology
                [2 ]College of Science
                [3 ]Northwest A&F University
                [4 ]Yangling
                [5 ]People's Republic of China
                Article
                DOI: 10.1039/C6CC03637F
                SO-VID: 7e7ae946-a11c-48ae-bf44-4db575636faa
                Copyright © © 2016
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