Ring-Opening Polymerization of Prodrugs: A Versatile Approach to Prepare Well-Defined Drug-Loaded Nanoparticles

The synthesis of polymer–drug conjugates from prodrug monomers consisting of a cyclic polymerizable group that is appended to a drug through a cleavable linker is achieved by organocatalyzed ring‐opening polymerization. The monomers polymerize into well‐defined polymer prodrugs that are designed to...

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Published in:Angewandte Chemie 2015-01, Vol.127 (3), p.1016-1020
Main Authors: Liu, Jinyao, Liu, Wenge, Weitzhandler, Isaac, Bhattacharyya, Jayanta, Li, Xinghai, Wang, Jing, Qi, Yizhi, Bhattacharjee, Somnath, Chilkoti, Ashutosh
Format: Article
Language:eng ; ger
Subjects:
Chemical compounds
Chemistry
Drug delivery systems
Drugs
Glycols
Krebstherapie
Monomers
Nanoparticles
Nanopartikel
Polymer-Wirkstoff-Konjugate
Polymerisierbare Prodrugs
Polymerization
Ringöffnungspolymerisation
Therapy
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cited_by cdi_FETCH-LOGICAL-c2333-2c5d3c4be06cc72f4f31395d0685f1b8fc9054b17e4266351fb73d68797f02a3
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container_title Angewandte Chemie
container_volume 127
creator Liu, Jinyao
Liu, Wenge
Weitzhandler, Isaac
Bhattacharyya, Jayanta
Li, Xinghai
Wang, Jing
Qi, Yizhi
Bhattacharjee, Somnath
Chilkoti, Ashutosh
description The synthesis of polymer–drug conjugates from prodrug monomers consisting of a cyclic polymerizable group that is appended to a drug through a cleavable linker is achieved by organocatalyzed ring‐opening polymerization. The monomers polymerize into well‐defined polymer prodrugs that are designed to self‐assemble into nanoparticles and release the drug in response to a physiologically relevant stimulus. This method is compatible with structurally diverse drugs and allows different drugs to be copolymerized with quantitative conversion of the monomers. The drug loading can be controlled by adjusting the monomer(s)/initiator feed ratio and drug release can be encoded into the polymer by the choice of linker. Initiating these monomers from a poly(ethylene glycol) macroinitiator results in amphiphilic diblock copolymers that spontaneously self‐assemble into micelles with a long plasma circulation, which is useful for systemic therapy. Konjugate: Biologisch abbaubare Polymer‐Wirkstoff‐Konjugate wurden durch die lebende Ringöffnungspolymerisation von Prodrug‐Monomeren aufgebaut. Letztere bestehen aus einer cyclischen polymerisierbaren Gruppe, die über einen spaltbaren Linker mit dem Wirkstoff verknüpft ist. Die Polymer‐Wirkstoff‐Konjugate selbstorganisieren zu Nanopartikeln und setzen den Wirkstoff als Reaktion auf physiologisch relevante Reize frei.
doi_str_mv 10.1002/ange.201409293
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The monomers polymerize into well‐defined polymer prodrugs that are designed to self‐assemble into nanoparticles and release the drug in response to a physiologically relevant stimulus. This method is compatible with structurally diverse drugs and allows different drugs to be copolymerized with quantitative conversion of the monomers. The drug loading can be controlled by adjusting the monomer(s)/initiator feed ratio and drug release can be encoded into the polymer by the choice of linker. Initiating these monomers from a poly(ethylene glycol) macroinitiator results in amphiphilic diblock copolymers that spontaneously self‐assemble into micelles with a long plasma circulation, which is useful for systemic therapy. Konjugate: Biologisch abbaubare Polymer‐Wirkstoff‐Konjugate wurden durch die lebende Ringöffnungspolymerisation von Prodrug‐Monomeren aufgebaut. Letztere bestehen aus einer cyclischen polymerisierbaren Gruppe, die über einen spaltbaren Linker mit dem Wirkstoff verknüpft ist. 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Chem</addtitle><description>The synthesis of polymer–drug conjugates from prodrug monomers consisting of a cyclic polymerizable group that is appended to a drug through a cleavable linker is achieved by organocatalyzed ring‐opening polymerization. The monomers polymerize into well‐defined polymer prodrugs that are designed to self‐assemble into nanoparticles and release the drug in response to a physiologically relevant stimulus. This method is compatible with structurally diverse drugs and allows different drugs to be copolymerized with quantitative conversion of the monomers. The drug loading can be controlled by adjusting the monomer(s)/initiator feed ratio and drug release can be encoded into the polymer by the choice of linker. Initiating these monomers from a poly(ethylene glycol) macroinitiator results in amphiphilic diblock copolymers that spontaneously self‐assemble into micelles with a long plasma circulation, which is useful for systemic therapy. Konjugate: Biologisch abbaubare Polymer‐Wirkstoff‐Konjugate wurden durch die lebende Ringöffnungspolymerisation von Prodrug‐Monomeren aufgebaut. Letztere bestehen aus einer cyclischen polymerisierbaren Gruppe, die über einen spaltbaren Linker mit dem Wirkstoff verknüpft ist. 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Initiating these monomers from a poly(ethylene glycol) macroinitiator results in amphiphilic diblock copolymers that spontaneously self‐assemble into micelles with a long plasma circulation, which is useful for systemic therapy. Konjugate: Biologisch abbaubare Polymer‐Wirkstoff‐Konjugate wurden durch die lebende Ringöffnungspolymerisation von Prodrug‐Monomeren aufgebaut. Letztere bestehen aus einer cyclischen polymerisierbaren Gruppe, die über einen spaltbaren Linker mit dem Wirkstoff verknüpft ist. Die Polymer‐Wirkstoff‐Konjugate selbstorganisieren zu Nanopartikeln und setzen den Wirkstoff als Reaktion auf physiologisch relevante Reize frei.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ange.201409293</doi><tpages>5</tpages></addata></record>
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source Wiley-Blackwell Read & Publish Collection
subjects Chemical compounds
Chemistry
Drug delivery systems
Drugs
Glycols
Krebstherapie
Monomers
Nanoparticles
Nanopartikel
Polymer-Wirkstoff-Konjugate
Polymerisierbare Prodrugs
Polymerization
Ringöffnungspolymerisation
Therapy
title Ring-Opening Polymerization of Prodrugs: A Versatile Approach to Prepare Well-Defined Drug-Loaded Nanoparticles
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