Preparation of lactic acid- and glucose-responsive poly(epsilon-caprolactone)-b-poly(ethylene oxide) block copolymer micelles using phenylboronic ester as a sensitive block linkage
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F18%3A10386218" target="_blank" >RIV/00216208:11310/18:10386218 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1039/c7nr09427b" target="_blank" >https://doi.org/10.1039/c7nr09427b</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c7nr09427b" target="_blank" >10.1039/c7nr09427b</a>
Alternative languages
Result language
angličtina
Original language name
Preparation of lactic acid- and glucose-responsive poly(epsilon-caprolactone)-b-poly(ethylene oxide) block copolymer micelles using phenylboronic ester as a sensitive block linkage
Original language description
The present study describes the synthesis, self-assembly and responsiveness to glucose and lactic acid of biocompatible and biodegradable block copolymer micelles using phenylboronic ester as the linkage between hydrophobic poly(epsilon-caprolactone) (PCL) and hydrophilic poly(ethylene oxide) (PEO). The PCL block with pendant phenylboronic acid (PCLBA) was synthesized by combining epsilon-caprolactone (epsilon-CL) ring-opening polymerisation (ROP), using 4-hydroxymethyl(phenylboronic) acid pinacolate as the initiator, and pinacol deprotection. The glucose-terminated PEO (PEOGlc) was prepared by 1,3-dipolar, Cu(I)-catalysed, alkyne-azide cycloaddition of alpha-methoxy-omega-propargyl poly(ethylene oxide) and 1-azido-1-deoxy-D-glucopyranose. All new compounds were evaluated by H-1 NMR spectroscopy and by SEC analysis. PCLBA and PEOGlc blocks were linked in NaOH acetone solution, which was indirectly confirmed by Alizarin Red S fluorescence and directly by H-1 NMR spectroscopy. Dialysis against Milli-Q water induced the self-assembly of PCLBA-b-PEOGlc nanoparticles, which were characterised by static (SLS) and dynamic (DLS) light scattering and by cryogenic transmission electron microscopy (cryo-TEM). Furthermore, the microscopic properties of the charged interface between the hydrophobic PCLBA core and the hydrophilic PEOGlc shell were examined by electrophoretic light scattering (zeta potential) and by fluorescence spectroscopy using the fluorescent probe 5-(N-dodecanoyl)aminofluorescein (DAF) as a pH indicator. Subsequently, the nanoparticles were transferred to a phosphate buffer saline (PBS) solution supplemented with different concentrations of glucose to simulate the physiological conditions in blood or lactic acid to simulate acidic cytosolic or endosomal conditions in tumour cells. Adding a surplus of glucose or lactic acid, which competitively binds to PBA, removes the stabilising hydrophilic PEOGlc blocks, thereby triggering marked nanoparticle aggregation. However, the rate of aggregation induced by lactic acid is considerably faster than that induced by glucose, as confirmed by light scattering. Thus, this novel block copolymer may contribute to the field of selective, lactic acid-and/or glucose-responsive drug delivery vehicle design under both pathological and physiological conditions.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10404 - Polymer science
Result continuities
Project
<a href="/en/project/GJ17-00289Y" target="_blank" >GJ17-00289Y: Sugar and pH-responsive multicompartment nano-assemblies for dual-drug solubilization and delivery</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Nanoscale
ISSN
2040-3364
e-ISSN
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Volume of the periodical
10
Issue of the periodical within the volume
18
Country of publishing house
GB - UNITED KINGDOM
Number of pages
15
Pages from-to
8428-8442
UT code for WoS article
000432096400011
EID of the result in the Scopus database
2-s2.0-85046894546