Bifunctional CDK9 Inhibitor Conjugates for Proteasomal Degradation

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Solution Overview

Problem

Current treatments for diseases involving cyclin-dependent kinase 9 (CDK9) lack effective alternative strategies, with most inhibitors failing due to systemic concentration issues and the need for novel mechanisms of action.

Innovation Solution

Development of bifunctional compounds that recruit CDK9 to E3 ubiquitin ligases for targeted degradation, utilizing a Targeting Ligand to bind CDK9 and a Linker-Degron moiety to facilitate proteasomal degradation, thereby modulating CDK9 levels.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If conventional CDK9 inhibitors are used, then CDK9 activity is inhibited, but the drugs fail to achieve high systemic concentrations and lack efficacy

Engineering Contradiction:
Improvesystemic drug concentrationVSAvoidclinical efficacy
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The inhibitor is divided into two functional segments: a CDK9-targeting ligand portion and an E3 ligase-binding moiety portion, connected by a linker. This segmentation allows each segment to perform its specific function independently while working together to achieve targeted degradation, resolving the contradiction between achieving sufficient concentration and maintaining efficacy.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The bifunctional compound acts as an intermediary that bridges CDK9 and the E3 ubiquitin ligase system. By introducing this intermediary molecule, the patent enables targeted ubiquitination and degradation of CDK9, overcoming the limitations of conventional inhibitors that could not achieve both adequate systemic concentration and clinical efficacy.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

If reversible CDK binders are used, then CDK activity is inhibited, but irreversible binders demonstrate superior performance

Engineering Contradiction:
Improveinhibitor efficacyVSAvoidbinding mechanism complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent merges reversible binding (CDK9-targeting ligand) with irreversible degradation (E3 ligase-mediated ubiquitination) into a single bifunctional mechanism. This combination achieves the reliability of irreversible binding while maintaining the selectivity and controllability of reversible binding, resolving the contradiction between efficacy and mechanism complexity.

Inventive Principle:
Principle #5Merging (Combining)

3Quantity of substance

If most known CDK inhibitors are used, then CDK activity is blocked, but they fail in clinic trials due to insufficient systemic concentration

Engineering Contradiction:
Improvesystemic drug concentrationVSAvoidclinical applicability
Core Design Contradiction:
Quantity of substanceVSAdaptability or versatility

Solution Approach 1:

The bifunctional compound utilizes the cell's own ubiquitin-proteasome system to degrade CDK9, rather than relying on external accumulation of inhibitor molecules. This self-service mechanism bypasses the limitation of achieving sufficient systemic concentration, as the degradation is triggered locally at the target site, thereby improving both concentration availability and clinical applicability.

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

The bifunctional compounds demonstrate specificity and efficacy in degrading CDK9, offering a novel approach to treating diseases like cancer by effectively reducing CDK9 levels and overcoming resistance issues.

Implementation Method 1

The covalent attachment of ubiquitin to specific protein substrates is achieved through the action of E3 ubiquitin ligases

Methodology Applied
Scientific EffectUbiquitination:

Implementation Method 2

the proteins recognized by CRBN are ubiquitinated and degraded by proteasomes

Methodology Applied
Scientific EffectProteasomal degradation:

Data Source

PatentEP3445760B1Degradation of cyclin-dependent kinase 9 (CDK9) by conjugation of CDK9 inhibitors with e3 ligase ligand and methods of use
Publication Date: 2022.02.23 DANA FARBER CANCER INSTITUTE INC
  • EP3445760B1 patent drawingFigure 1
  • EP3445760B1 patent drawingFigure 2
  • EP3445760B1 patent drawingFigure 3

AI summary

The present application provides bifunctional compounds of Formula (I): Targeting Ligand or a pharmaceutically acceptable salt, hydrate, solvate, prodrag, stereoisomer, or tautomer thereof, which act as protein degradation inducing moieties for cyclin-dependent kinase 9 (CDK.9). The present application also relates to methods for the targeted degradation of CDK9 through the use of th e bifunctional compounds that link a ubiquitin ligase-binding moiety to a ligand that is capable of binding to CDK9 which can be utilized in the treatment of disorders modulated by CDK9.