Branched Phosphorylcholine Polymer Conjugates for Biologics

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Solution Overview

Problem

Current biologically active agents face challenges such as immunogenicity, short biological half-life, and limited solubility, leading to frequent administration and potential pain, especially when conjugated with linear PEG polymers, which can result in loss of biological activity and inappropriate degradation rates.

Innovation Solution

Development of branched phosphorylcholine-containing polymers, specifically poly[2-(methacryloyloxyethyl)-2'-(trimethylammonium)ethyl phosphate], to covalently bond with biologically active agents, enhancing solubility, stability, and reducing immunogenicity, while maintaining biological activity and optimizing degradation rates.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If linear PEG polymers are used for conjugation, then solubility and stability are improved, but biological activity is lost and degradation rates are inappropriate

Engineering Contradiction:
ImprovestabilityVSAvoidbiological activity
Core Design Contradiction:
Stability of the object's compositionVSReliability

Solution Approach 1:

The patent changes the chemical structure parameters of the polymer from linear PEG to branched phosphorylcholine-containing polymers with specific molecular weights and architectures. This structural parameter change allows the polymer to provide stability through its branched configuration while the phosphorylcholine groups maintain biological compatibility and activity, resolving the contradiction between stability and biological activity.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses composite polymer structures combining branched architecture with phosphorylcholine functional groups. This composite approach creates a polymer that exhibits both the stability benefits of branched structures and the biological compatibility of phosphorylcholine, thereby maintaining biological activity while achieving enhanced stability.

Inventive Principle:
Principle #40Composite materials

2Object-affected harmful factors

If PEG conjugation is performed, then immunogenicity is reduced, but biological activity is lost

Engineering Contradiction:
ImproveimmunogenicityVSAvoidbiological activity
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The patent modifies the polymer parameters by replacing PEG with phosphorylcholine-containing polymers that have similar or superior properties. The phosphorylcholine groups are known to be highly biocompatible and non-immunogenic, while their branched configuration provides steric protection that maintains biological activity, thus resolving the contradiction between reduced immunogenicity and maintained biological activity.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If frequent administration is required, then therapeutic effect is maintained, but pain and inconvenience increase

Engineering Contradiction:
Improvetherapeutic effectVSAvoidconvenience
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent employs polymer conjugation that provides partial protection - the branched polymer structure offers steric shielding without completely masking the biological agent. This partial protection extends the half-life sufficiently to reduce dosing frequency while maintaining therapeutic effectiveness, thereby improving convenience without sacrificing therapeutic effect.

Inventive Principle:
Principle #16Partial or excessive action

4Quantity of substance

If long linear PEG polymers are used, then solubility is improved, but biological activity is blocked

Engineering Contradiction:
ImprovesolubilityVSAvoidbiological activity
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The patent segments the polymer structure into branched configurations rather than using long linear chains. The branched architecture provides solubility benefits through increased hydrodynamic volume and water interaction, while the segmented structure prevents the polymer from wrapping around and blocking the biological agent, thus maintaining biological activity while improving solubility.

Inventive Principle:
Principle #1Segmentation

Data Source

PatentEP1988910B1Acryloyloxyethylphosphorylcholine containing polymer conjugates and their preparation
Publication Date: 2017.12.06 KODIAK SCIENCES INC
  • EP1988910B1 patent drawingFigure 1~2
  • EP1988910B1 patent drawingFigure 3
  • EP1988910B1 patent drawingFigure 4

AI summary

The present invention relates to polymeric reagents and conjugates thereof, methods for synthesizing the polymeric reagents and conjugates, pharmaceutical compositions comprising the conjugates and methods of using the polymer conjugates including therapeutic methods where conjugates are administered to patients.