Journal
BIOMACROMOLECULES
Volume 16, Issue 12, Pages 3731-3739Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.biomac.5b01325
Keywords
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Funding
- Ministry of Education, Youth and Sport of the Czech Republic [7AMB13PL025]
- Czech Science Foundation Grant [P205/14-14608S]
- Polish Ministry of Science and Higher Education [8771/R13/R14]
- Faculty of Chemistry, Warsaw University of Technology
- Czech Science Foundation [P302/12/G157]
- Charles University in Prague [Prvouk/1LF/1, UNCE204022]
- European Union through Warsaw University of Technology Development Programme
- Center of Advanced Studies at Charles University in Prague
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Coassembly behavior of the double hydrophilic block copolymer poly(4-hydroxystyrene)-block-poly(ethylene oxide) (PHOS-PEO) with three amphiphilic phenylboronic acids (PBA) differing in hydrophobicity, 4-dodecyloxyphenylboronic acid (C12), 4-octyloxyphenylboronic acid (C8), and 4-isobutoxyphenylboronic acid (i-Bu) was studied in alkaline aqueous solutions and in mixtures of NaOHaq/THF by spin echo H-1 NMR spectroscopy, dynamic and electrophoretic light scattering, and SAXS. The study reveals that only the coassembly of C12 with PHOS PEO provides spherical nanoparticles with intermixed PHOS and PEO blocks, containing densely packed C12 micelles. NMR measurements have shown that spatial proximity of PHOS-PEO and C12 leads to the formation of ester bonds between OH of PHOS block and hydroxyl groups of -B(OH)(2). Due to the presence of PBA moieties, the release of compounds with 1,2- or 1,3-dihydroxy groups loaded in the coassembled PHOS-PEO/PBA nanoparticles by covalent binding to PBA can be triggered by addition of a surplus of glucose that bind to PBA competitively. The latter feature has been confirmed by fluorescence measurements using Alizarin Red as a model compound. Nanoparticles were proved to exhibit swelling in response to glucose as detected by light scattering.
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