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Dual pH‐Sensitive DOX‐Conjugated Cyclodextrin‐Core Star Nano‐Copolymer Prodrugs
Author(s) -
Hou Yu,
Liu Yuyang,
Sun Shuangshuang,
Liang Jianghu
Publication year - 2017
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201700068
Subject(s) - ethylene glycol , copolymer , methacrylate , micelle , atom transfer radical polymerization , chemistry , polymer chemistry , conjugated system , aqueous solution , cyclodextrin , polymer , organic chemistry
Herein this study reports dual pH‐sensitive doxorubicin (DOX)‐conjugated β‐cyclodextrin‐core star copolymers with tailoring properties such as direct water‐solubility and stability prior to reaching target sites. For these purposes, three kinds of novel well‐defined β‐cyclodextrin‐core poly(2‐(diethylamino)ethyl methacrylate‐ co ‐4‐formylphenyl methacrylate)‐ b ‐poly(poly(ethylene glycol) methyl ether methacrylate) star copolymers (CD‐star‐P(DEA‐ co ‐FPMA)‐ b ‐PPEGMA, SPDFP1–3) with different poly(ethylene glycol) methyl ether methacrylate contents are designed and synthesized by atom transfer radical polymerization (ATRP) strategy. 4‐Formylphenyl methacrylate is introduced into the inner arm block of the star copolymers for conjugating DOX by imine bond formation. Interestingly, the DOX‐conjugated β‐cyclodextrin‐core star copolymers not only can directly dissolve in aqueous buffer solution of pH 7.0 to form unimolecular micelles without any aid of organic solvent, but also exhibit strong pH‐dependent DOX release. At normal pH 7.4 the DOX amount released is very small, whereas at pH 5.0 DOX can be released. By selecting SPDFP2–DOX as a representative, it is found that the SPDFP2–DOX micelles show less cytotoxicity compared to carrier‐free DOX and can be internalized by HeLa cells. It is expected that the exploration can provide new strategy for preparing drug delivery system.