Multifunctional Nitroxide Derivatives for Oxidative Stress

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Solution Overview

Problem

Current treatments for oxidative stress and endothelial dysfunction often require co-administration of separate potassium channel openers and antioxidants, which face challenges due to unpredictable tissue distribution, metabolism, and intracellular localization, limiting their effectiveness.

Innovation Solution

Development of multifunctional nitroxide derivatives that combine potassium channel opening and reactive oxygen species degradation properties, specifically the oxy radical of 2-cyano-1-(1-hydroxy-2,2,5,5-tetramethylpyrrolidin-3-yl)-3-(pyridin-3-yl) guanidine, to simultaneously target oxidative stress and endothelial dysfunction.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If separate potassium channel openers and antioxidants are co-administered, then therapeutic coverage is improved, but treatment complexity and unpredictability increase

Engineering Contradiction:
Improvetherapeutic coverageVSAvoidtreatment complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent combines a potassium channel opener (pinacidil) and an antioxidant (tempol) into a single conjugate molecule. This merging of two separate therapeutic agents into one compound allows simultaneous delivery of both functions, reducing treatment complexity while maintaining broad therapeutic coverage for oxidative stress and endothelial dysfunction

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The conjugate molecule serves multiple therapeutic functions simultaneously: it acts as both a potassium channel opener and an antioxidant. This multi-functionality allows a single compound to address multiple pathological mechanisms involved in ischemia-reperfusion injury, inflammatory conditions, and oxidative stress-related diseases

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

2Adaptability or versatility

If separate potassium channel openers and antioxidants are co-administered, then therapeutic coverage is improved, but reliability decreases due to unpredictable tissue distribution and metabolism

Engineering Contradiction:
Improvetherapeutic coverageVSAvoidtissue distribution predictability
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

By covalently linking the potassium channel opener and antioxidant into a single conjugate molecule, the patent ensures that both therapeutic agents are delivered together to the same tissue compartments. This eliminates the variability associated with separate administration, as the fixed molecular structure guarantees consistent co-delivery and metabolic fate

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The conjugate molecule self-delivers both therapeutic functions simultaneously to target tissues. The unified structure ensures that the compound's pharmacokinetic properties (distribution, metabolism, excretion) apply equally to both functional moieties, creating predictable and reliable therapeutic exposure without requiring coordinated administration of separate agents

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

These derivatives effectively reduce myocardial and renal injury, attenuate inflammation, and provide protective effects in ischemia-reperfusion injuries and acute chlorine inhalation, without causing systemic hypotension or affecting blood glucose levels.

Implementation Method 1

multifunctional nitroxide derivatives that combine potassium channel opening and reactive oxygen species degradation properties

Methodology Applied
Scientific EffectSuperoxide dismutase activity: Catalysis

Implementation Method 2

Openers of the mitochondrial ATP-regulated potassium channel have been shown to provide cytoprotection in experimental models of redox stress

Methodology Applied
Scientific EffectIon channel opening:

Data Source

PatentEP2649048B1Multifunctional nitroxide derivatives and uses thereof
Publication Date: 2016.03.30 RADIKAL THERAPEUTICS INC
  • EP2649048B1 patent drawingFigure 1
  • EP2649048B1 patent drawingFigure 2A~2B
  • EP2649048B1 patent drawingFigure 3A~3C

AI summary

The present invention provides multifunctional nitroxide derivatives comprising a potassium channel opener and a reactive oxygen species (ROS) degradation catalyst that can act as an anti-oxidant, as well as pharmaceutical compositions comprising them. The multifunctional compounds and pharmaceutical compositions of the invention are useful for treatment of diseases, disorders or conditions associated with oxidative stress or endothelial dysfunction.