Premium
Photo‐ and pH‐ Dual‐Responsive β‐Cyclodextrin‐Based Supramolecular Prodrug Complex Self‐Assemblies for Programmed Drug Delivery
Author(s) -
Bai Yang,
Liu Cai Ping,
Song Xin,
Zhuo Longhai,
Bu Huaitian,
Tian Wei
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201801366
Subject(s) - prodrug , supramolecular chemistry , cyclodextrin , dynamic light scattering , amphiphile , micelle , chemistry , azobenzene , combinatorial chemistry , drug delivery , methacrylate , biophysics , nanotechnology , materials science , organic chemistry , nanoparticle , copolymer , aqueous solution , biochemistry , molecule , polymer , biology
Despite the fact that progress has been made in the application of supramolecular prodrug self‐assemblies to enhance the functionality of drug‐delivery systems, corresponding research on multi‐responsive supramolecular prodrug self‐assemblies for programmed drug delivery is still limited. In this paper, the synthesis and self‐assembly behavior of supramolecular prodrug complexes (SPCs) with β‐cyclodextrin–acylhydrazone–doxorubicin (β ‐ CD ‐ hydrazone ‐ DOX) and the targeting of azobenzene‐terminated poly[2‐(dimethylamino)ethyl methacrylate] (Azo‐PDMA‐FA) as a building block were investigated. The obtained SPCs could also form self‐assemblies on the basis of their amphiphilic nature. Next, SPC‐based multi‐compartment vesicles and complex micelles, which were confirmed by transmission electron microscopy and dynamic/static light scattering, were obtained with good reversibility under alternative visible light or UV irradiation. Furthermore, three‐stage programmed drug‐delivery behavior was observed from dual‐responsive SPC‐based self‐assemblies by utilizing UV and pH stimuli. Specifically, the SPCs first self‐assembled into multicompartmental vesicles, which was accompanied by a slow release of DOX. Next, UV‐light irradiation induced the dissociation of β‐CD/Azo, which led to morphology transition and a slight increase in the rate of release of DOX. Upon transferring the self‐assemblies to phosphate‐buffer solution (pH 5.0), the release rates increased notably as a result of the broken acylhydrazone bond. Finally, basic cell experiments further demonstrated that the SPC‐based self‐assemblies could be internalized into cancer cells, which suggests their promise for applications in cancer therapy.