Triarylpyridine compounds for lysosomal membrane permeabilization

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Solution Overview

Problem

Current anticancer therapies face challenges due to cancer cells becoming chemoresistant, with lysosomes playing a role in drug resistance by sequestering anticancer agents, and existing G-quadruplex ligands have limitations in efficacy against cancer cells.

Innovation Solution

Development of new triarylpyridine compounds that induce cancer cell death through lysosomal membrane permeabilization, potentially synergized with lysosomotropic agents like chloroquine to enhance their effectiveness.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing G-quadruplex ligands are used to inhibit cancer proliferation, then cancer cell growth is suppressed to some extent, but the compounds fail to achieve sufficient efficacy and cancer remains life-threatening

Engineering Contradiction:
Improveanticancer efficacyVSAvoidcancer cell death rate
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent modifies the chemical structure of G-quadruplex ligands by changing molecular parameters - specifically incorporating triarylpyridine core with varying aryl substituents (R1-R6 groups) to optimize binding affinity and cellular penetration, thereby enhancing anticancer efficacy

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite therapeutic strategies by combining triarylpyridine compounds with lysosomotropic agents (such as chloroquine), where the combination synergistically enhances cancer cell death through multiple mechanisms including G4 stabilization and lysosomal membrane permeabilization

Inventive Principle:
Principle #40Composite materials

2Reliability

If lysosomes are targeted to overcome chemoresistance, then drug resistance is reduced, but new compounds must be designed to achieve lysosomal membrane permeabilization which increases development complexity

Engineering Contradiction:
Improvechemoresistance reversalVSAvoidcompound structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The triarylpyridine compounds are designed to perform multiple functions simultaneously: binding to G-quadruplex DNA structures, penetrating cancer cell membranes, and inducing lysosomal membrane permeabilization, thereby reducing the need for multiple separate agents

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

Solution Approach 2:

The patent introduces lysosomotropic properties to the compounds through specific structural features that enable selective accumulation and action in lysosomes, creating localized high concentration effects at the target site while maintaining overall compound stability

Inventive Principle:
Principle #3Local quality

3Reliability

If combination therapy with lysosomotropic agents is used, then synergistic efficacy is achieved, but treatment protocol complexity increases

Engineering Contradiction:
Improvesynergistic anticancer effectVSAvoidcombination therapy protocol
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent merges the functions of G-quadruplex stabilization and lysosomal membrane permeabilization induction into a single compound class (triarylpyridines), which can then be combined with lysosomotropic agents to create synergistic effects that target multiple resistance mechanisms simultaneously

Inventive Principle:
Principle #5Merging (Combining)

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 new triarylpyridine compounds demonstrate improved activity in inducing cancer cell death, particularly through lysosomal membrane permeabilization, and show a synergistic effect when combined with chloroquine, surpassing the efficacy of existing compounds like 20A.

Implementation Method 1

G-quadruplexes (G4s) are four-stranded non-canonical nucleic acids secondary structures which form in guanine-rich DNA and RNA sequences. Many G-quadruplex forming sequences are found to be associated with cancer. Some compounds, named G-quadruplex interactive ligands (or G-quadruplex ligands, or G4 ligands, abbreviated as G4L) have been shown to strongly interact with G-quadruplex DNA and to inhibit cancer proliferation

Methodology Applied
Scientific EffectG-quadruplex interaction:

Implementation Method 2

Lysosomal dependent non-apoptotic cell death is of tremendous interest in cancer therapy as cancer cells often display defective apoptotic machinery rendering them resistant to therapy. The new triarylpyridine compounds demonstrate improved activity in inducing cancer cell death, particularly through lysosomal membrane permeabilization

Methodology Applied
Scientific EffectLysosomal membrane permeabilization:

Implementation Method 3

There is a need to provide new compounds with a lysosomotropic effect. The new triarylpyridine compounds show a synergistic effect when combined with chloroquine, surpassing the efficacy of existing compounds like 20A

Methodology Applied
Scientific EffectLysosomotropic effect:

Data Source

PatentEP4157458B1Triarylpyridine compounds and use thereof for treating cancer
Publication Date: 2024.04.17 INST NAT DE LA SANTE & DE LA RECHERCHE MEDICALE (INSERM)
  • EP4157458B1 patent drawingFigure 1
  • EP4157458B1 patent drawingFigure 2
  • EP4157458B1 patent drawingFigure 3

AI summary

The invention relates to new bis-triazole 2,4,6-triarylpyridines compounds and their use in the field of oncology, in particular in the prevention and/or treatment of cancer disease. The inventors have observed that the new bis-triazole 2,4,6-triarylpyridines were able to induce cancer cells death either as a standalone or, synergistically, in combination with a lysosomotropic agent, such as chloroquine. The compounds were active against a variety of cancer cells such as HeLa (cervical cancer cell), A549 (lung carcinoma), and PDX-2 or PDX-3 (lung adenocarcinoma). The invention also relates to compositions and methods for prevention and/or treatment of cancer diseases using the new bis-triazole 2,4,6-triarylpyridines compounds.