PROTAC Small Molecules for E3 Ligase Degradation

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Solution Overview

Problem

E3 ubiquitin ligases pose challenges for drug design due to their deep and 'druggable' active sites, leading to high inhibitor concentrations and off-target effects, and current inhibitors often fail to effectively target these enzymes for degradation.

Innovation Solution

Development of Proteolysis-Targeting Chimeras (PROTACs) compounds that comprise two E3 ubiquitin ligase binding moieties linked by a linker, enabling the formation of ternary complexes where one E3 ligase ubiquitinates another, inducing proteasomal degradation at sub-stoichiometric concentrations.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional small-molecule inhibitors are used to target E3 ligases, then inhibitor concentration must be high to achieve effective binding, but this leads to off-target effects and reduced selectivity

Engineering Contradiction:
ImproveselectivityVSAvoidinhibitor concentration
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The PROTAC molecule is segmented into three functional modules: two E3 ligase binding moieties (A and B) and a central linker (L). This segmentation allows each module to perform its specific function independently - binding to E3 ligases and facilitating dimerization - while working together to achieve the overall goal of selective target degradation at low concentrations

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The PROTAC compound acts as an intermediary molecule that mediates the interaction between two E3 ligases. By serving as a bridge, it enables the formation of a ternary complex where one E3 ligase ubiquitinates the other, allowing selective target engagement without requiring high concentrations of the inhibitor itself

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

If high concentrations of inhibitors are used to overcome the lack of deep active sites in E3 ligases, then binding effectiveness may improve, but off-target effects increase

Engineering Contradiction:
Improvebinding effectivenessVSAvoidoff-target effects
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The invention merges two E3 ligase binding moieties into a single PROTAC molecule, creating a bivalent compound that can simultaneously engage two E3 ligases. This merging strategy enhances binding effectiveness through avidity effects while maintaining selectivity, as the dual binding requirement creates a more specific interaction profile

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The PROTAC compound represents a composite molecular structure combining elements from different E3 ligase binders (A and B) connected by a linker (L). This composite design allows the molecule to leverage the specific binding properties of both moieties, achieving enhanced binding effectiveness while reducing off-target effects through the cooperative interaction of multiple binding sites

Inventive Principle:
Principle #40Composite materials

3Reliability

If current inhibitors target E3 ligase substrate recognition sites, then some inhibition activity is achieved, but degradation of the E3 ligase itself does not occur

Engineering Contradiction:
Improveinhibition activityVSAvoidtarget degradation efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

Instead of simply inhibiting E3 ligase activity, the PROTAC inverts the approach by recruiting E3 ligases to form a complex where one E3 ligase becomes the substrate for another. This inversion transforms the E3 ligase from the target of inhibition into the target of degradation, achieving both inhibition activity and enhanced productivity through proteasomal degradation

Inventive Principle:
Principle #13The other way round (Inversion)

Solution Approach 2:

The PROTAC system utilizes the cell's own ubiquitin-proteasome machinery to degrade the target E3 ligase. By recruiting endogenous E3 ligases through the PROTAC-mediated ternary complex, the system achieves target degradation through self-service mechanisms, eliminating the need for external degradation enzymes or complex delivery systems

Inventive Principle:
Principle #25Self-service

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

PROTACs achieve selective and sustained target protein degradation with lower concentrations than conventional inhibitors, overcoming compensatory feedback mechanisms and providing enhanced selectivity and efficacy in degrading E3 ligases.

Implementation Method 1

one E3 ubiquitin ligase protein ubiquitinates another E3 ubiquitin ligase protein to which it is joined by the compound of structure A-L-B

Methodology Applied
Scientific EffectUbiquitination: Chemical Bonding

Implementation Method 2

triggering their subsequent proteasomal degradation

Methodology Applied
Scientific EffectProteasomal degradation: Decomposition (biological)

Data Source

PatentEP3609889B1Small molecules
Publication Date: 2023.07.05 UNIVERSITY OF DUNDEE
  • EP3609889B1 patent drawingFigure 1a~1b
  • EP3609889B1 patent drawingFigure 2a~2c
  • EP3609889B1 patent drawingFigure 3

AI summary

Compounds having the general structure A - L - B are presented wherein A and B are independently an E3 ubiquitin ligase protein binding ligand compound of formula 1A or 1 B. Pharmaceutical compositions comprising these compounds and methods of use are also presented.