Facile Synthesis of H₂O₂-Cleavable Poly(ester-amide)s by Passerini Multicomponent Polymerization

Area of Science:

• Polymer Chemistry
• Materials Science
• Biomedical Engineering

Background:

• Development of responsive polymers is crucial for advanced drug delivery systems.
• Hydrogen peroxide (H2O2) is a key biomarker for various physiological and pathological conditions.
• Existing H2O2-cleavable polymers often require complex synthesis or harsh conditions for degradation.

Purpose of the Study:

• To report the straightforward synthesis of novel H2O2-cleavable poly(ester-amide)s.
• To investigate the H2O2-triggered degradation mechanism and kinetics of these polymers.
• To demonstrate the potential of these polymers as H2O2-responsive drug delivery vehicles.

Main Methods:

• Synthesis of poly(ester-amide)s (P1 and P2) via Passerini multicomponent polymerization.
• Incorporation of H2O2-cleavable phenylboronic acid ester into the polymer backbone.
• Characterization using Gel Permeation Chromatography (GPC) and 1H Nuclear Magnetic Resonance (NMR) spectroscopy.
• Fabrication of nanoparticles and drug release studies.

Main Results:

• Successfully synthesized two types of H2O2-cleavable poly(ester-amide)s (P1 and P2).
• Confirmed complete polymer degradation triggered by H2O2 via oxidation and self-immolative elimination.
• PEG-based polymer P2 showed faster degradation than hydrophobic polymer P1 in aqueous media.
• Demonstrated controlled release of Nile red from P1 nanoparticles in response to H2O2.

Conclusions:

• The synthesized poly(ester-amide)s offer a facile route to H2O2-responsive materials.
• Polymer degradation is efficiently triggered by H2O2, with tunable rates based on polymer structure.
• These polymers show promise as cytocompatible, H2O2-responsive delivery vehicles for therapeutic agents.