Degradable Photoreactive Linking Agent for Medical Device Coatings

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Solution Overview

Problem

Current technologies lack a degradable linking agent that can covalently attach to surfaces or target molecules upon activation, enabling reversible properties in medical devices and coatings, particularly for applications like bioactive agent delivery and tissue engineering where biodegradability is crucial.

Innovation Solution

A degradable linking agent with photoreactive groups, such as aryl ketones like benzophenone, and phosphorester/phosphoramide bonds, which form covalent bonds with surfaces or molecules upon activation, allowing for controlled degradation and reversible properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a permanent coating is applied to a medical device, then the coating provides durable protection and functionality, but it cannot be removed or degraded, requiring surgical removal and causing additional trauma

Engineering Contradiction:
Improvecoating durabilityVSAvoidsurgical removal complexity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies the dynamics principle by creating a coating system that transitions from a stable, durable state to a degradable state. The coating is designed with hydrolytically labile linkers that remain stable during initial use but can be activated to degrade over time or upon stimulation, allowing the coating to change its properties from permanent to temporary based on physiological conditions or external triggers.

Inventive Principle:
Principle #15Dynamics

Solution Approach 2:

The patent employs parameter changes by modifying the chemical structure of the coating's linker molecules to include hydrolytically labile bonds. These linkers have specific chemical parameters (bond stability, hydrolysis rate) that can be tuned to control degradation timing. The coating's degradation is achieved by changing the chemical integrity of the linker molecules through hydrolysis, allowing controlled removal without surgical intervention.

Inventive Principle:
Principle #35Parameter changes

2Strength

If a non-degradable linking agent is used to attach coatings, then strong covalent bonds provide stable attachment, but the coating cannot be removed or absorbed by tissues

Engineering Contradiction:
Improvecoating attachment strengthVSAvoidcoating retention time
Core Design Contradiction:
StrengthVSDuration of action of stationary object

Solution Approach 1:

The linking agent is designed with dynamic bond stability - strong covalent attachment initially, then controlled degradation. The hydrolytically labile linkers provide strong initial bonding to the substrate while containing chemical structures that will eventually hydrolyze, transforming the bond from permanent to temporary based on environmental conditions.

Inventive Principle:
Principle #15Dynamics

Solution Approach 2:

The linking agent's chemical parameters are specifically engineered to control bond strength and degradation timing. The hydrolytically labile linkers have tunable half-lives and degradation rates, allowing the attachment strength to change over time from strong and stable to progressively weaker as hydrolysis occurs, enabling controlled release without violent bond breaking.

Inventive Principle:
Principle #35Parameter changes

3Manufacturing precision

If photoreactive groups are used for covalent attachment, then precise control of bonding is achieved, but the process requires activation energy in the form of light exposure

Engineering Contradiction:
Improvebonding control precisionVSAvoidlight activation energy
Core Design Contradiction:
Manufacturing precisionVSUse of energy by moving object

Solution Approach 1:

The patent replaces the need for mechanical or chemical activation with optical activation. Instead of requiring chemical reagents or mechanical energy input to initiate bonding, the system uses photoreactive groups that activate upon light exposure. This substitution allows precise spatial and temporal control of the bonding process through light delivery, replacing complex chemical activation mechanisms with simpler optical control.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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

Enables the creation of coatings and devices with initial and subsequent properties, facilitating bioactive agent delivery and tissue engineering by providing a biodegradable scaffold that can be absorbed by tissues, reducing the need for surgical removal.

Implementation Method 1

Photochemically reactive functional groups ("photoreactive groups") are functional groups that, when exposed to an appropriate energy source, undergo a transformation from an inactive state (i.e., ground state) to a reactive intermediate capable of forming covalent bonds with appropriate materials.

Methodology Applied
Scientific EffectPhotochemical reaction: Photo-oxidation

Implementation Method 2

the linking agent is capable of, upon activation of one or more photoreactive groups, covalent attachment to a surface, target molecule, or a combination thereof

Methodology Applied
Scientific EffectCovalent bonding: Chemical Bonding

Data Source

PatentEP3581213B1Coated medical device
Publication Date: 2022.07.06 SURMODICS INC
  • EP3581213B1 patent drawingFigure 1~3
  • EP3581213B1 patent drawingFigure 4~6
  • EP3581213B1 patent drawingFigure 7~8

AI summary

Described herein is a coated medical device comprising: a medical device comprising a substrate, the substrate comprising a surface; and a polymeric coating disposed over the surface of the substrate, wherein the polymeric coating comprises a linking agent; and a polymer; wherein the linking agent comprises a compound of formula Photo1-P(O)(R)-Photo2 wherein Photo1 and Photo2, independently, represent one or more photoreactive groups, and wherein R is phenyl, methyl, ethyl, isopropyl, t-butyl, hydroxyl or a salt thereof.