Taxoid-Polymer Conjugates for Controlled Release

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Solution Overview

Problem

Current formulations of taxoids, such as paclitaxel and docetaxel, face challenges with low water solubility and poorly controlled release due to physical encapsulation methods, leading to instability and inefficient delivery.

Innovation Solution

Development of covalent conjugates of taxoids with functionalized copolymers of polyethylene glycol and polylactic acid, utilizing specific linkers like succinic acid, glutaric acid, or diglycolic acid to create nanoparticles with controlled release profiles and improved accessibility of the active principle.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If physical encapsulation of taxoids in nanoparticles is used, then water solubility is improved, but release control is poor and precipitation risk increases

Engineering Contradiction:
Improvewater solubilityVSAvoidrelease control
Core Design Contradiction:
Stability of the object's compositionVSReliability

Solution Approach 1:

The patent introduces a linker molecule as an intermediary between the taxoid and the polymer. This linker enables covalent bonding while maintaining the ability to control drug release through hydrolysis, thus resolving the contradiction between improving solubility and maintaining reliable release control

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the chemical state of the taxoid-polymer interaction from physical encapsulation to covalent conjugation. This parameter change enables both improved solubility through the hydrophilic polymer and controlled release through the hydrolyzable covalent bond

Inventive Principle:
Principle #35Parameter changes

2Reliability

If covalent conjugation of taxoids with polymers is implemented, then encapsulation control is improved, but accessibility of the active principle for hydrolysis is reduced

Engineering Contradiction:
Improveencapsulation controlVSAvoidaccessibility for hydrolysis
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent applies local quality by positioning the taxoid specifically at the hydrophobic/hydrophilic interface of the nanoparticle. This location provides both stable covalent encapsulation and optimal accessibility for hydrolytic cleavage, resolving the contradiction between encapsulation control and hydrolysis accessibility

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The linker serves as a mediator that connects the taxoid to the polymer while being positioned to facilitate hydrolysis. The linker's structure enables both controlled encapsulation and maintains accessibility for enzymatic or chemical cleavage

Inventive Principle:
Principle #24Intermediary (Mediator)

3Stability of the object's composition

If traditional formulations with cremophor and alcohol are used, then solubility is achieved, but side effects increase

Engineering Contradiction:
ImprovesolubilityVSAvoidside effects
Core Design Contradiction:
Stability of the object's compositionVSObject-affected harmful factors

Solution Approach 1:

The patent changes the formulation parameter from using toxic solvents (cremophor and alcohol) to using a biocompatible hydrophilic polymer. This parameter change maintains solubility while eliminating harmful side effects

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite material system consisting of the hydrophilic polymer, linker, and taxoid. This composite approach enables solubility enhancement without requiring toxic adjuvants, resolving the contradiction between achieving solubility and minimizing side effects

Inventive Principle:
Principle #40Composite materials

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

The covalent conjugation approach enables stoichiometric encapsulation, reduced precipitation, and controlled release of taxoids, enhancing their bioavailability and stability, particularly at the hydrophobic/hydrophilic interface, facilitating targeted delivery.

Implementation Method 1

functionalized copolymers of polyethylene glycol and polylactic acid... comprising a hydrophilic corona

Methodology Applied
Scientific EffectAmphiphilic self-assembly: Amphiphiles

Implementation Method 2

controlled release of the active principle by the linker... significantly improving the accessibility of the active principle for hydrolysis

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentEP2640422B1Polymeric conjugates of active principles, their process of preparation and their polymeric intermediates
Publication Date: 2017.03.01 SANOFI SA(FR)
  • EP2640422B1 patent drawingFigure 1~2
  • EP2640422B1 patent drawingFigure 3

AI summary

The present invention relates to novel conjugates of active principles grafted to a polymer, to the nanoparticles comprising them, to their preparation and to their polymeric intermediates.