Degradable Nanoparticles with Epoxide and Keto Functional Groups

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Solution Overview

Problem

Conventional biodegradable nanoparticles, particularly those based on poly(ε-caprolactone) and aliphatic polyesters, face challenges in reproducibility of particle size and shape due to stabilizer and solvent influences, and lack of pendant functional groups, which limits modification of physicochemical, mechanical, and biological properties.

Innovation Solution

Development of polymers with specific monomer residues, such as epoxide-functionalized, propargyl-functionalized, and keto-functionalized monomers, allowing for controlled copolymerization and cross-linking to produce degradable nanoparticles with tailored properties and reproducible size, and methods for functionalizing these nanoparticles with biologically active agents or imaging moieties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional methods using stabilizers and solvents are employed to produce biodegradable nanoparticles, then particle formation is achieved, but particle size and shape become irreproducible

Engineering Contradiction:
Improveparticle size and shape reproducibilityVSAvoidconsistency of particle properties
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The patent changes the chemical parameters of the polymer by incorporating specific functional monomers (epoxide, propargyl, keto) that enable controlled crosslinking. This parameter change in polymer structure allows for reproducible particle formation without relying on stabilizers and solvents, directly addressing the inconsistency issue in conventional methods

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite polymer structures by copolymerizing multiple monomer types (epoxide-functionalized, propargyl-functionalized, keto-functionalized monomers) to form a multifunctional polymer system. This composite approach enables simultaneous control of particle morphology and functionalization, achieving both size reproducibility and enhanced properties

Inventive Principle:
Principle #40Composite materials

2Adaptability or versatility

If poly(ε-caprolactone) and aliphatic polyesters are used as base materials, then biodegradability is achieved, but pendant functional groups are lacking for property modification

Engineering Contradiction:
Improveability to modify physicochemical and biological propertiesVSAvoidpolymer structure complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent segments the polymer structure by incorporating distinct functional monomer units (epoxide, propargyl, keto) as separate repeat units within the polymer chain. Each monomer type provides specific functionality, allowing modular modification of particle properties while maintaining the biodegradable polyester backbone

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent creates multifunctional polymers that simultaneously provide biodegradability (from the polyester backbone), crosslinking capability (from epoxide and propargyl groups), and additional functionalization sites (from keto groups). This multi-functionality in a single polymer system enables comprehensive property control without requiring multiple different polymer materials

Inventive Principle:
Principle #6Universality (Multi-functionality)

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 approach enables the creation of nanoparticles with precise size control and functionalization, enhancing their biological and therapeutic applications by modifying hydrophilicity, biodegradation rate, and bioadhesion, thus overcoming the limitations of conventional methods.

Implementation Method 1

copolymerizing a mixture of two or more of an alkene-functionalized monomer providing a residue having an optionally substituted structure represented by a formula (VI)

Methodology Applied
Scientific EffectCopolymerization: Chemical Bonding

Implementation Method 2

a method of preparing an epoxide-functionalized polymer comprising the step of oxidizing a polymer having at least one monomer residue having an optionally substituted structure represented by a formula (VI)

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 3

a method of crosslinking a polymer comprising the step of reacting a polymer comprising at least one monomer residue selected from an epoxide-functionalized monomer residue

Methodology Applied
Scientific EffectCross-linking: Chemical Bonding

Data Source

PatentEP2209496B1Multifunctional degradable nanoparticles with control over size and functionalities
Publication Date: 2019.05.08 VANDERBILT UNIV
  • EP2209496B1 patent drawingFigure 1
  • EP2209496B1 patent drawingFigure 2
  • EP2209496B1 patent drawingFigure 3~4

AI summary

In one aspect, the invention relates to polymers, crosslinked polymers, functionalized polymers, nanoparticles, and functionalized nanoparticles and methods of making and using same. In one aspect, the invention relates to degradable polymer and degradable nanoparticles. In one aspect, the invention relates to methods of preparing degradable nanoparticles and, more specifically, methods of controlling particle size during the preparation of degradable nanoparticles. In one aspect, the degradable nanoparticles are useful for complexing, delivering, and releasing payloads, including pharmaceutically active payloads. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.