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Furoxan‐Bearing Micelles for Nitric Oxide Delivery
Author(s) -
Hasegawa Urara,
Wang Tengjiao,
Chen Jerry J. Y.,
Uyama Hiroshi,
van der Vlies André J.
Publication year - 2016
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/mabi.201500401
Subject(s) - micelle , furoxan , copolymer , amphiphile , chemistry , polymer chemistry , polymerization , chain transfer , nitric oxide , organic chemistry , polymer , radical polymerization , aqueous solution
Furoxans, or 1,2,5‐oxadiazole‐ N ‐oxides, are a class of nitric oxide (NO)‐donating compounds that release NO in response to thiol‐containing molecules. In this study, polymeric micelles bearing furoxan moieties are prepared from an amphiphilic block copolymer consisting of a hydrophobic furoxan‐bearing block and a hydrophilic poly( N ‐acryloylmorpholine) block. The block copolymer is prepared using a combination of the reversible addition–fragmentation chain transfer polymerization and the copper‐catalyzed Huisgen cycloaddition techniques. The block copolymers form spherical micelles with a diameter of 50 nm by self‐assembly in water. The micelles release NO in response to cysteine and show improved stability against hydrolytic decomposition. Furthermore, the micelles show a synergistic anti‐proliferative effect with ibuprofen in human colon cancer cells.