N-acetylcysteine amide antioxidant permeates cell membranes

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Solution Overview

Problem

Current antioxidant therapies, such as vitamins E and C, are inadequate in addressing oxidative stress due to limited ability to cross cell membranes and the blood-brain barrier, necessitating the development of more potent and effective antioxidant compounds that can easily permeate cells and the brain.

Innovation Solution

The use of N-acetylcysteine amide (NAC amide), a low molecular weight thiol antioxidant, which readily permeates cell membranes and the blood-brain barrier, recycling oxidized biomolecules and providing protective effects against oxidative stress.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If vitamins E and C are used as antioxidants, then antioxidant effects are provided, but their ability to cross cell membranes and the blood-brain barrier is limited

Engineering Contradiction:
Improveantioxidant effectivenessVSAvoidcell membrane permeability
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent modifies the chemical structure of cysteine by converting the carboxylic acid group to an amide group, creating N-acetylcysteine amide. This parameter change in molecular structure dramatically improves lipid solubility and membrane permeability while maintaining antioxidant activity through the thiol group.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention combines the antioxidant properties of cysteine with the enhanced membrane permeability characteristics of amide compounds. The resulting N-acetylcysteine amide integrates both functions into a single molecular entity that can effectively cross biological barriers and provide antioxidant protection.

Inventive Principle:
Principle #40Composite materials

2Quantity of substance

If glutathione is supplied to tissues, then cellular antioxidant levels are maintained, but distribution to peripheral tissues is inadequate

Engineering Contradiction:
Improveantioxidant levelsVSAvoidtissue distribution
Core Design Contradiction:
Quantity of substanceVSEase of operation

Solution Approach 1:

The patent changes the molecular parameters of the antioxidant compound by using N-acetylcysteine amide instead of glutathione. This lower molecular weight compound with modified chemical structure achieves superior tissue distribution and penetration while maintaining effective antioxidant concentrations in peripheral tissues.

Inventive Principle:
Principle #35Parameter changes

3Object-affected harmful factors

If high doses of antioxidants are administered, then oxidative stress is reduced, but the compounds cannot reach intracellular targets effectively

Engineering Contradiction:
Improveoxidative stressVSAvoidcellular uptake
Core Design Contradiction:
Object-affected harmful factorsVSEase of operation

Solution Approach 1:

The patent modifies the chemical parameters of the antioxidant to create N-acetylcysteine amide, which has enhanced lipophilicity and membrane permeability. This allows the compound to effectively reach intracellular targets at lower doses compared to hydrophilic antioxidants like vitamins C and E.

Inventive Principle:
Principle #35Parameter changes

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

NAC amide effectively reduces oxidative stress, improves mitochondrial function, and treats conditions like cataracts, retinal pigment epithelial dysfunction, and spinal cord injuries by enhancing cellular antioxidant levels and reducing oxidative damage.

Implementation Method 1

NAC amide, a low molecular weight thiol antioxidant, which readily permeates cell membranes and the blood-brain barrier

Methodology Applied
Scientific EffectPermeation: Permeation

Implementation Method 2

NAC amide can recycle oxidized biomolecules back to their active reduced forms and may be as effective, if not more effective, than GSH as an antioxidant

Methodology Applied
Scientific EffectRedox reactions: Redox Reactions

Data Source

PatentEP2841064B1Use of n-acetylcysteine amide in the treatment of cataracts
Publication Date: 2019.06.12 SENTIENT LIFESCI
  • EP2841064B1 patent drawingFigure 1~2
  • EP2841064B1 patent drawingFigure 3~4
  • EP2841064B1 patent drawingFigure 5~6

AI summary

This disclosure describes methods of use for N-acetylcysteine amide for the treatment of various disorders