Related Experiment Video
Updated: Sep 16, 2025

Anionic Polymerization of an Amphiphilic Copolymer for Preparation of Block Copolymer Micelles Stabilized by π-π Stacking Interactions
Published on: October 10, 2016
Synthesis and Characterization of Polymer-Drug Conjugates by Strain-Promoted Azide-Alkyne Cycloaddition-Mediated
Omotola D Gbadegesin1, Simeon K Adesina1
1Department of Pharmaceutical Sciences, Howard University, Washington DC, USA.
Abstract:
Polymer-drug conjugates (PDCs) modify the biodistribution of small-molecule anticancer agents to prevent undesired off-target adverse effects. Here, we report the preparation of two PDCs by strain-promoted [3 + 2] azide-alkyne cycloaddition-mediated step-growth polymerization. This method does not require the use of a catalyst or high temperatures and it allows the rapid synthesis of high molecular-weight PDCs containing gemcitabine (Mw ~ 40.18 kDa) and doxorubicin (Mw ~ 1800 kDa) with narrow molecular weight distribution and high drug loading (29.2 %wt. gemcitabine and 10.3 %wt. doxorubicin). α-ω-bis-azide-terminated bifunctional gemcitabine-coupled and doxorubicin-coupled monomers, with drug linkage via Gly-Phe-Leu-Gly (GFLG), a cathepsin B-sensitive peptide linker, were separately synthesized and polymerized using a dibenzoazacyclooctyne bifunctional polyethylene glycol monomer. Preliminary in vitro evaluations of the PDCs showed cathepsin B-catalyzed drug release at pH 5.0. The applied method for the syntheses of the PDCs enables the selective delivery of potent anticancer agents.
Related Concept Videos
Ziegler–Natta Chain-Growth Polymerization: Overview
Cationic Chain-Growth Polymerization: Mechanism
Anionic Chain-Growth Polymerization: Overview
Step-Growth Polymerization: Overview
Many natural and synthetic polymers are produced by...
Polymers
Phase II Conjugation Reactions: Overview

