A New Class of Degradable Polymers with Medical, Agricultural and Materials Applications

Tech ID: W-14-028

Background

There has been significant interest and an urgent environmental need for the development of degradable polymers for a wide range of applications including environmentally friendly plastics, adhesives, biomedical sutures, tissue engineering scaffolds, and drug delivery vehicles. The preparation of biodegradable polymeric materials based on monomers derived from renewable, nonpetroleum resources is particularly attractive as these materials are potentially more sustainable than hydrocarbon-based materials and often degrade into nontoxic metabolic intermediates. While polymers such as poly(lactic acid), polycaprolactone, poly(glycolic acid), chitosan and hyaluronic acid have been investigated in many different applications, their degradation is relatively slow and nonspecific, limiting their use where more immediate degradation is needed.

To overcome this slow non-specific degradation, the development of stimuli-responsive polymers has also been a highly active area of research over the past couple of decades. Self-immolative polymers are an interesting class of stimuli-responsive materials as they depolymerize to small molecules through a cascade of reactions following cleavage of the polymer backbone or a specific terminal or focal point moiety by a stimulus. The stimulus to induce degradation can be tuned based on the capping agent used to stabilize the polymer.

Technology Overview

Researchers at Western University have developed a new family of end-capped self-immolative poly(ethyl glyoxylate)s that can respond to a variety of stimuli, including ultraviolet light, reactive oxygen species, acid, and temperature changes. Poly(ethyl glyoxylate)s are particularly attractive, as the monomer used to from the polymer, ethyl glyoxylate, is commercially available on large scales. Poly(ethyl glyoxylate)s have been shown to degrade to ethyl alcohol as well as glyoxylic acid hydrate, an intermediate in the glyoxylic acid cycle, and ultimately to CO₂ in the environment.

Benefits

• Monomers commercially available on a large scale
• Tunable degradation to specific stimuli applied
• Fast degradation if desired

Applications

This technology has commercial application in the following fields:

• Medicine: As biomedical sutures, tissue engineering scaffolds, and drug/gene delivery vehicles.
• Agricultural: As coatings for fertilizers
• Materials: As degradable adhesives, coatings, materials for surface patterning/printing

Recent publications:

Development of Fertilizer Coatings from Polyglyoxylate–Polyester Blends Responsive to Root-Driven pH Change. J. Agric. Food Chem. 2019, 67, 46, 12720–12729

Self-immolative polyplexes for DNA delivery. Biomater. Sci., 2022, 10, 2557‑2567

Poly(ethyl glyoxylate)-Poly(ethylene oxide) Nanoparticles: Stimuli-Responsive Drug Release via End-to-End Polyglyoxylate Depolymerization. Mol. Pharmaceutics 2017, 14, 8, 2548–2559

Opportunity

• Licensing
• Partnerships
• Collaborative Research

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