Pipecolic Esters Inhibit Proteasome via Alpha-Ring Binding

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Solution Overview

Problem

Current proteasome inhibitors used in cancer treatment are toxic and develop resistance, and there is a lack of effective allosteric proteasome modulation strategies.

Innovation Solution

Development of compounds with specific structures that target the 20S proteasome's α-ring, inhibiting proteolytic activity without affecting the mTOR pathway, and are capable of modifying the proteasome in cells to treat uncontrolled cellular proliferation disorders.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If current proteasome inhibitors are used for cancer treatment, then proteasome activity is inhibited, but toxicity and resistance development occur

Engineering Contradiction:
Improveproteasome inhibition efficacyVSAvoidtoxicity and resistance
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent introduces an intermediary compound (pipecolic acid derivative) that indirectly inhibits proteasome activity by binding to the α-ring region, rather than directly competing with substrate at the catalytic site. This intermediary mechanism of action provides effective proteasome inhibition while avoiding the toxicity and resistance issues associated with conventional direct inhibitors like boronic acids and epoxysuccinyl compounds.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the binding parameter location from the catalytic β-subunit site to the α-ring region of the proteasome. By altering the binding site parameter, the compound achieves proteasome inhibition through a different mechanism, resulting in improved therapeutic profile with reduced toxicity and resistance development compared to conventional inhibitors.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If rapamycin and its metabolites are used, then proteasome inhibition is achieved, but mTOR pathway interference occurs

Engineering Contradiction:
Improveproteasome inhibitionVSAvoidselectivity for proteasome vs mTOR
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies local quality by designing a compound that specifically targets the α-ring region of the proteasome with high selectivity. The pipecolic acid derivative structure is optimized to bind locally at the α-ring interface, providing focused proteasome inhibition without affecting other pathways such as mTOR, thus achieving high adaptability and selectivity.

Inventive Principle:
Principle #3Local quality

3Reliability

If competitive inhibitors targeting catalytic subunits are used, then proteasome activity is blocked, but allosteric modulation potential is lost

Engineering Contradiction:
Improveproteasome inhibitionVSAvoidinhibition mechanism simplicity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

Instead of following the conventional approach of designing competitive inhibitors that bind to catalytic subunits, the patent inverts the strategy by developing an inhibitor that binds to the α-ring region. This inverted approach enables allosteric modulation of proteasome activity, providing a more complex but effective inhibition mechanism that overcomes the limitations of simple competitive inhibition.

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

Data Source

PatentEP3746440B1Pipecolic esters for inhibition of the proteasome
Publication Date: 2023.07.05 BOARD OF RGT THE UNIV OF TEXAS SYST
  • EP3746440B1 patent drawingFigure 1
  • EP3746440B1 patent drawingFigure 2
  • EP3746440B1 patent drawingFigure 3A~3B

AI summary

The present disclosure relates to chemical compounds that modulate proteasome activity, pharmaceutical compositions containing such compounds, and use of these compounds and compositions for the treatment of disorders of uncontrolled cellular proliferation such as, for example, a cancer. 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.