Methyl-β-cyclodextrin inclusion complexes for stable PUFAs

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Solution Overview

Problem

Polyunsaturated fatty acids (PUFAs) face challenges in pharmaceutical compositions due to poor solubility in water and chemical stability, leading to unstable ophthalmic formulations, particularly for inflammatory ocular pathologies, where existing methods like emulsions and suspensions result in physical and chemical degradation.

Innovation Solution

An aqueous solution comprising polyunsaturated fatty acids with free carboxylic function (PUFAs FFA) and methyl-β-cyclodextrins (Met-β-CD) provides chemical and physical stability without using heterogeneous systems, with preferred concentrations of PUFAs between 0.01-0.10% w/w and Met-β-CD between 1.0-10% w/w, buffered at physiological pH, and optionally including viscous polymers, osmotizing agents, and preservatives.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If PUFAs are used in aqueous solutions, then water solubility is improved, but chemical stability deteriorates due to oxidation

Engineering Contradiction:
Improvewater solubilityVSAvoidchemical stability
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The patent introduces methyl-β-cyclodextrin as an intermediary substance that forms inclusion complexes with PUFAs. This mediator protects the PUFAs from direct contact with water while maintaining solubility, thereby preventing oxidation and improving chemical stability without sacrificing water solubility.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent creates a composite aqueous solution system combining PUFAs, methyl-β-cyclodextrin, and buffer agents. This composite formulation synergistically improves both solubility and stability by integrating multiple components that work together to protect PUFAs from degradation while maintaining aqueous solubility.

Inventive Principle:
Principle #40Composite materials

2Quantity of substance

If emulsion systems are used to improve solubility, then water solubility is improved, but physical stability deteriorates due to phase separation

Engineering Contradiction:
Improvewater solubilityVSAvoidphysical stability
Core Design Contradiction:
Quantity of substanceVSStability of the object's composition

Solution Approach 1:

Methyl-β-cyclodextrin acts as a molecular bridge that solubilizes PUFAs in water without forming emulsions. The cyclodextrin inclusion complexes provide a molecular-level dissolution mechanism that avoids the macroscopic phase separation issues inherent in emulsion systems, thereby maintaining physical stability.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the fundamental solubilization mechanism from emulsion-based (macroscopic mixing) to inclusion complex-based (molecular-level integration). This parameter change in the solubilization approach eliminates the need for heterogeneous emulsion structures, thereby preventing phase separation while maintaining water solubility.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If esterified PUFAs are used, then chemical stability is improved, but biological activity deteriorates due to rapid degradation

Engineering Contradiction:
Improvechemical stabilityVSAvoidbiological activity
Core Design Contradiction:
ReliabilityVSDuration of action of moving object

Solution Approach 1:

Methyl-β-cyclodextrin serves as a protective intermediary that allows free PUFAs to remain stable in aqueous solution. The inclusion complex formation prevents oxidation and degradation of free PUFAs, thereby maintaining both chemical stability and biological activity without requiring esterification.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the chemical state of PUFAs from esterified to free acid form, while compensating for the usual instability through the addition of methyl-β-cyclodextrin. This parameter change in PUFA form is combined with a protective environmental modification (inclusion complex formation) to achieve both stability and activity.

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

The composition maintains stability over 24 months at room temperature with PUFAs titers above 95%, unlike esterified forms which degrade rapidly, and demonstrates improved ocular tolerance and stability compared to other cyclodextrin formulations.

Implementation Method 1

stable watersoluble compositions for ophthalmic use comprising one or more N-acylethanolamines in the form of an inclusion complex in methyl-β-cyclodextrin

Methodology Applied
Scientific EffectInclusion complex formation: Solvation

Data Source

PatentEP3700507B1Stable aqueous solutions comprising pufas
Publication Date: 2021.10.20 MEDIVIS SRL

AI summary

The present invention relates to a composition for ophthalmic use comprising one or more polyunsaturated fatty acids with free carboxylic function (PUFAs FFA) in aqueous solution with methyl-β-cyclodextrins (Met-β-CD), wherein said PUFAs are selected from the group comprising omega-3 and omega-6 polyunsaturated fatty acids, said polyunsaturated fatty acids having an aliphatic chain of from 16 to 24 carbon atoms. The ophthalmic use of said composition is a further object.