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Reduction‐Sensitive, Robust Vesicles with a Non‐covalently Modifiable Surface as a Multifunctional Drug‐Delivery Platform
Author(s) -
Park Kyeng Min,
Lee DonWook,
Sarkar Bijay,
Jung Hyuntae,
Kim Jeeyeon,
Ko Young Ho,
Lee Kyung Eun,
Jeon Hyesung,
Kim Kimoon
Publication year - 2010
Publication title -
small
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 3.785
H-Index - 236
eISSN - 1613-6829
pISSN - 1613-6810
DOI - 10.1002/smll.201000293
Subject(s) - conjugate , drug delivery , doxorubicin , chemistry , cytotoxicity , covalent bond , combinatorial chemistry , spermidine , surface modification , endocytosis , targeted drug delivery , nanotechnology , materials science , biophysics , biochemistry , receptor , biology , organic chemistry , in vitro , mathematical analysis , mathematics , chemotherapy , genetics , enzyme
Abstract The design and synthesis of a novel reduction‐sensitive, robust, and biocompatible vesicle (SSCB[6]VC) are reported, which is self‐assembled from an amphiphilic cucurbit[6]uril (CB[6]) derivative that contains disulfide bonds between hexaethylene glycol units and a CB[6] core. The remarkable features of SSCB[6]VC include: 1) facile, non‐destructive, non‐covalent, and modular surface modification using exceptionally strong host–guest chemistry; 2) high structural stability; 3) facile internalization into targeted cells by receptor‐mediated endocytosis, and 4) efficient triggered release of entrapped drugs in a reducing environment such as cytoplasm. Furthermore, a significantly increased cytotoxicity of the anticancer drug doxorubicin to cancer cells is demonstrated using doxorubicin‐loaded SSCB[6]VC, the surface of which is decorated with functional moieties such as a folate–spermidine conjugate and fluorescein isothiocyanate–spermidine conjugate as targeting ligand and fluorescence imaging probe, respectively. SSCB[6]VC with such unique features can be used as a highly versatile multifunctional platform for targeted drug delivery, which may find useful applications in cancer therapy. This novel strategy based on supramolecular chemistry and the unique properties of CB[6] can be extended to design smart multifunctional materials for biomedical applications including gene delivery.