Photoresponsive biodegradable poly(carbonate)s with pendent<i>o</i>‐nitrobenzyl ester

Shen, Huihui; Xia, Yingchun; Qin, Zhouliang; Wu, Juan; Zhang, Li; Lu, Yanbing; Xia, Xinnian; Xu, Weijian

doi:10.1002/pola.28679

Cited by 14 publications

(5 citation statements)

References 59 publications

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“…Aliphatic cyclic carbonates are a versatile and widely used monomer scaffold for the preparation of polycarbonates, copolymers, and non-isocyanate polyurethanes. − These materials find application in a variety of domains including drug-delivery vehicles, − antimicrobial materials, − macromolecular chemotherapeutics, , covalent adaptable networks, materials for three-dimensional (3D) printing, surface patterning, , heavy-metal sequestration, magnetic resonance imaging contrast agents, computed tomography imaging, solid-phase electrolytes for ion transport, , and luminescent polymers for white light generation . One of the most commonly used monomer precursors is 2,2-bis(hydroxymethyl)propionic acid (bis-MPA; Figure A) as the installment of various functional groups via esterification enables fine-tuning of the properties of the derived polymers.…”

Section: Introductionmentioning

confidence: 99%

Overcoming Barriers in Polycarbonate Synthesis: A Streamlined Approach for the Synthesis of Cyclic Carbonate Monomers

Hedrick

Arrechea

et al. 2021

Macromolecules

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Accessing cyclic carbonate monomers on a large scale is critical for the development of any new carbonate-based materials platform. The synthesis of carbonate monomers can be a challenging and tedious endeavor requiring multiple synthetic steps and purifications. To address this, we report a drastically improved process for the synthesis of carbonate monomers via a two-step route that avoids the use of hazardous triphosgene or chloroformate reagents. This process enables rapid access to a broad array of functional groups on the carbonate monomer and the monomers generated from the procedure can readily be polymerized via ring-opening polymerization.

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Section: Introductionmentioning

confidence: 99%

Overcoming Barriers in Polycarbonate Synthesis: A Streamlined Approach for the Synthesis of Cyclic Carbonate Monomers

Hedrick

Arrechea

et al. 2021

Macromolecules

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“…In recent years, aliphatic polycarbonates (APCs) have been intensively studied and used as materials in the biomedical and pharmaceutical fields due to their low toxicity, good biocompatibility, and biodegradability. − In contrast to other approaches to obtain APCs, such as polycondensation of diols with dialkyl carbonates − and copolymerization of CO 2 and epoxides, , the ring-opening polymerization (ROP) is the most important method to synthesize functionalized APCs with controlled molar masses and polymer structures. − Although the degradation rates of APCs could be accelerated under acid, basic, or enzymatic environment, the controlled degradation of APCs upon internal or external stimuli, such as pH, − temperature, , oxidation, − enzyme, and light, − is of great interest for their biomedical applications, such as drug or gene delivery systems. Among various stimuli, the degradation rate of light-responsive polymers can be controlled by adjusting light wavelength, intensity or duration of the irradiation, while other stimuli (e.g., pH, oxidation) only provide limited control and acceleration of the decomposition process over the time. , …”

Section: Introductionmentioning

confidence: 99%

Use of Light-Degradable Aliphatic Polycarbonate Nanoparticles As Drug Carrier for Photosensitizer

et al. 2018

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Aliphatic 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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“…Lu and coworkers have continued to develop novel light-responsive APC nanocarriers. PEGylated APC with pendent o-nitrobenzyl ester group was reported [145]. The photo-cleavage nature of the o-nitrobenzyl ester group into the free carboxylic acid group and o-nitrosobenzaldehyde under UV light irradiation caused micelles disassembly and the release of the encapsulated drug.…”

Section: Light-responsive Apc Nanocarriersmentioning

confidence: 99%

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

et al. 2020

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Nanoparticles based on amphiphilic copolymers with tunable physicochemical properties can be used to encapsulate delicate pharmaceutics while at the same time improving their solubility, stability, pharmacokinetic properties, reducing immune surveillance, or achieving tumor-targeting ability. Those nanocarriers based on biodegradable aliphatic polycarbonates are a particularly promising platform for drug delivery due to flexibility in the design and synthesis of appropriate monomers and copolymers. Current studies in this field focus on the design and the synthesis of new effective carriers of hydrophobic drugs and their release in a controlled manner by exogenous or endogenous factors in tumor-specific regions. Reactive groups present in aliphatic carbonate copolymers, undergo a reaction under the action of a stimulus: e.g., acidic hydrolysis, oxidation, reduction, etc. leading to changes in the morphology of nanoparticles. This allows the release of the drug in a highly controlled manner and induces a desired therapeutic outcome without damaging healthy tissues. The presented review summarizes the current advances in chemistry and methods for designing stimuli-responsive nanocarriers based on aliphatic polycarbonates for controlled drug delivery.

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Photoresponsive biodegradable poly(carbonate)s with pendento‐nitrobenzyl ester

Cited by 14 publications

References 59 publications

Overcoming Barriers in Polycarbonate Synthesis: A Streamlined Approach for the Synthesis of Cyclic Carbonate Monomers

Overcoming Barriers in Polycarbonate Synthesis: A Streamlined Approach for the Synthesis of Cyclic Carbonate Monomers

Use of Light-Degradable Aliphatic Polycarbonate Nanoparticles As Drug Carrier for Photosensitizer

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

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