Biodegradable Trehalose Polyester for Protein Stabilization

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Solution Overview

Problem

Current protein-polymer conjugates, particularly those using poly(ethylene glycol) (PEG), face challenges such as non-biodegradability, immunological responses, and decreased bioactivity due to steric shielding, necessitating the development of biodegradable polymers that stabilize proteins and can be readily synthesized for chronic therapeutic applications.

Innovation Solution

The development of biodegradable zwitterion polymers with a polyester backbone and trehalose side chains, which are synthesized using controlled radical polymerization and thiol-ene chemistry, providing stability against environmental stressors and degrading through ester hydrolysis, thus addressing the limitations of existing PEG-based conjugates.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If poly(ethylene glycol) (PEG) is used for protein conjugation, then protein stability against environmental stressors is improved, but biodegradability deteriorates causing tissue accumulation

Engineering Contradiction:
Improveprotein stabilityVSAvoidbiodegradability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical composition parameters of the polymer from non-biodegradable PEG to biodegradable polyesters with pendant functional groups, maintaining the protein-stabilizing function while enabling biodegradation through ester bond hydrolysis

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite polymer structures combining a biodegradable polyester backbone with pendant functional groups (such as hydroxyl, carboxyl, or amine groups) that provide protein-stabilizing properties, integrating both biodegradability and stability functions in a single material system

Inventive Principle:
Principle #40Composite materials

2Reliability

If PEG is used for protein conjugation, then protein stability is improved, but immunological responses worsen including accelerated blood clearance

Engineering Contradiction:
Improveprotein stabilityVSAvoidimmunological responses
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the polymer material from PEG to biodegradable polyesters, fundamentally altering the chemical composition to eliminate immunogenicity while preserving the steric protection function that stabilizes proteins

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs transient polymers that perform their protective function temporarily and then degrade into harmless byproducts, replacing the persistent PEG molecules that cause immunological issues with short-lived biodegradable alternatives

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

3Duration of action of moving object

If protein-polymer conjugation is performed, then treatment duration is extended, but bioactivity deteriorates due to steric shielding of the protein active site

Engineering Contradiction:
Improvetreatment durationVSAvoidbioactivity
Core Design Contradiction:
Duration of action of moving objectVSReliability

Solution Approach 1:

The patent applies local quality by positioning pendant functional groups at specific locations on the polymer chain that provide steric protection without blocking the protein active site, allowing different regions of the conjugate to have different functions

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent segments the polymer structure into a backbone providing extended circulation time and pendant functional groups providing localized stabilization, separating the functions of duration extension and activity maintenance into distinct structural elements

Inventive Principle:
Principle #1Segmentation

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

These biodegradable zwitterion polymers effectively stabilize proteins and biomolecules under stress conditions, maintaining bioactivity and degrading into non-cytotoxic products, offering a promising alternative to PEG-based conjugates for chronic therapies.

Implementation Method 1

degrading through ester hydrolysis

Methodology Applied
Scientific EffectEster hydrolysis: Hydrolysis

Implementation Method 2

synthesized using controlled radical polymerization and thiol-ene chemistry

Methodology Applied
Scientific EffectThiol-ene reaction: Photopolymerisation

Data Source

PatentEP3342796B1Substituted polyesters by thiol-ene modification: rapid diversification for therapeutic protein stabilization
Publication Date: 2024.08.07 RGT UNIV OF CALIFORNIA
  • EP3342796B1 patent drawingFigure 1
  • EP3342796B1 patent drawingFigure 2
  • EP3342796B1 patent drawingFigure 3

AI summary

Structures and methods of making biodegradable trehalose co-polymers are disclosed. Specifically, biodegradable trehalose co-polymers consist of the general structure R5-[R1R2C - CR3R4]n-[DG]m-R6, wherein R1-R4 are independently selected from hydrogen or a side chain comprising at least one carbon atom, and wherein at least one of R1-R4 is a side chain comprising -L-trehalose, wherein L is a linker molecule that links trehalose to the monomer through at least one of the trehalose hydroxyl groups (-OH), wherein DG is a biodegradable group, and wherein R5 and R6 are end groups.