Preparation of Light‐Responsive Aliphatic Polycarbonate via Versatile Polycondensation for Controlled Degradation

Abstract

Starting from (2,2,5‐trimethyl‐1,3‐dioxan‐5‐yl)methanamine with light‐responsive 4,5‐dimethoxy‐2‐nitrobenzyl protecting groups, a variety of light‐responsive copolycarbonates (LrPCs) are synthesized by a general two‐step polycondensation using lithium acetylacetonate (LiAcac) as catalyst. UV/Vis, 1H nuclear magnetic resonance (NMR), and size exclusion chromatography (SEC) confirm the rapid decomposition of these polymers in response to irradiation with UV light. Stable and monodisperse nanoparticles with hydrodynamic diameters of 100 nm, formulated from 25% LrPC and 75% poly(lactic‐co‐glycolic acid) (PLGA), undergo rapid disruption upon triggering with UV light, while standard PLGA nanoparticles remain stable. Moreover, differing from the ring‐opening polymerization (ROP) of trimethylene carbonate‐based monomers, direct polycondensation of 1,3‐propanediol‐based monomers with pendent functional groups and other diols will enable the introduction of various properties into the polycarbonate backbone, and expand the family of biodegradable synthetic polymers for potential biomedical applications.

Remote Light‐Responsive Nanocarriers for Controlled Drug Delivery: Advances and Perspectives

“…By exploiting similar strategy, Kuckling and Sun have recently developed a new light‐responsive aliphatic polycarbonate (LrPC) for delivery of the photosensitizer 5,10,15,20‐tetrakis (m‐hydroxyphenyl)chlorin (mTHPC) ( Figure ). Multiple photocleavable oNB groups were conjugated within this LrPC polymer as side chains . UV light irradiation (λ = 320–480 nm) resulted in the cleavage of the oNB protecting groups, followed by the rapid degradation of the polymers via intramolecular cyclization.…”

“…Multiple photocleavable oNB groups were conjugated within this LrPC polymer as side chains. [38,55,56] UV light irradiation (λ = 320-480 nm) resulted in the cleavage of the oNB protecting groups, followed by the rapid degradation of the polymers via intramolecular cyclization. The light-induced reaction then led to the burst release of mTHPC.…”

Stimuli-Responsive Aliphatic Polycarbonate Nanocarriers for Tumor-Targeted Drug Delivery

“…Similarly, Fang et al [146] reported photo-responsive micelles consisting of PNIPAM-b-poly(3-methyl-3-nitrobenzyl-trimethylene carbonate) for indomethacin drug delivery system. Likewise, Kuckilng and coworkers developed a series of light-degradable nanocarriers consisting of PEGylated APC with an o-nitrobenzyl ester group as side chains [147][148][149][150][151]. The nanoparticles were prepared from mixing amphiphilic APC copolymer with poly(lactide-co-glycolide) in ratio 1:3 (Figure 9).…”

Light‐Responsive Serinol‐Based Polyurethane Nanocarrier for Controlled Drug Release

“…from other stimuli whose control is limited by time and location, drug release triggered by light can be precisely modulated by selecting suitable irradiation parameters regarding light wavelength, intensity, irradiation time, and spatial resolution. [11][12][13] Several light-responsive polymeric systems used as drug carriers have been explored to rapidly release encapsulated payload in exposure to UV light. [14][15][16][17] Recently, a novel o-nitrobenzyl (ONB)functionalized light-responsive aliphatic polycarbonate (LrPC) has been used as drug carrier for photosensitizer 5,10,15,20-tetrakis(m-hydroxyphenyl) chlorin (mTHPC).…”

“…Recently, PU nanoparticles with stimuli‐responsive properties, including pH, redox, and temperature sensitivity have been widely investigated as drug carriers. Differing from other stimuli whose control is limited by time and location, drug release triggered by light can be precisely modulated by selecting suitable irradiation parameters regarding light wavelength, intensity, irradiation time, and spatial resolution …”