bm8b01446_si_001.pdf (1.72 MB)
Use of Light-Degradable Aliphatic Polycarbonate Nanoparticles As Drug Carrier for Photosensitizer
journal contribution
posted on 2018-11-15, 00:00 authored by Jingjiang Sun, Wolfgang Birnbaum, Juliane Anderski, Marie-Theres Picker, Dennis Mulac, Klaus Langer, Dirk KucklingAliphatic
poly(carbonate)s (APCs) with rapid and controlled degradation
upon specific stimulation have great advantages for a variety of biomedical
and pharmaceutical applications. In the present work, we reported
a new poly(trimethylene carbonate) (PTMC)-based copolymer containing
multiple 4,5-dimethoxy-2-nitrobenzyl photo cleavable groups as pendent
chains. The six-membered light-responsive cyclic carbonate monomer
(LrM) was first prepared from 2-(hydroxymethyl)-2-methylpropane-1,3-diol
and 4,5-dimethoxy-2-nitrobenzyl alcohol and then copolymerized with
trimethylene carbonate (TMC) by 1,8-diazabicyclo(5.4.0)undec-7-ene
(DBU) catalyzed ring-opening polymerization (ROP) to afford the light-responsive
polycarbonate (LrPC). The light-triggered decomposition
of LrM and LrPC was studied by NMR, UV/vis
spectroscopy, and size exclusion chromatography (SEC), as well as
ESI-ToF mass spectrometry. Stable monodisperse nanoparticles with
hydrodynamic diameter of 100 nm could be formulated from 25% LrPC and 75% poly(lactide-co-glycolide) (PLGA)
and applied for the encapsulation of temoporfin. Upon irradiation
with UV light these particles displayed a significant decrease of
the particle countrate and increased the release rate of temoporfin
in comparison to standard PLGA nanoparticles. This work demonstrated
that a combination of encapsulation of photosensitizer and light degradation
using light-responsive polymers is suitable to enhance photodynamic
therapy (PDT).
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Keywords
LrMlight-responsive polycarbonatePTMCAPCDBUsix-membered light-responsive cyclic carbonate monomerring-opening polymerizationROPLrPCrelease ratesize exclusion chromatographyTMCtrimethylene carbonatependent chainshydrodynamic diameterSECPDTencapsulationESI-ToF mass spectrometryNMRPLGA nanoparticleslight-responsive polymerslight degradationphotodynamic therapyDrug CarrierdimethoxyLight-Degradable Aliphatic Polycarbonate Nanoparticleslight-triggered decompositionUV light100 nmparticle countratetemoporfin-2-nitrobenzyl
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