Cyclodextrin Clathrate Trisulfides for Water-Soluble Stability
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Solution Overview
Problem
Trisulfide compounds, such as those disclosed in Patent Literature 1, suffer from poor water solubility, limiting their applicability and stability in pharmaceutical formulations.
Innovation Solution
Development of trisulfide compounds with carboxylic acid amide and ester structures modified with hydrophilic functional groups, and their cyclodextrin clathrates, enhancing water solubility and stability.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional trisulfide compounds are used, then they possess oxidation-reduction ability and physiological activity, but they exhibit poor water solubility
Solution Approach 1:
The patent modifies the chemical structure of trisulfide compounds by introducing hydrophilic functional groups (carboxylic acid amide and ester groups) to change the solubility parameters while preserving the core trisulfide structure and its oxidation-reduction capability. This allows the compound to maintain physiological activity while achieving improved water solubility.
Solution Approach 2:
The patent creates composite structures by combining the hydrophobic lipoic acid core with hydrophilic functional groups, forming a amphiphilic molecule that integrates both water-insoluble and water-soluble characteristics. This composite approach enables the molecule to maintain its biological activity while achieving enhanced solubility in aqueous environments.
2Reliability
If cyclodextrin clathrate is formed, then water solubility and stability are improved, but molecular structure complexity increases
Solution Approach 1:
The patent uses cyclodextrin as an intermediary host molecule that forms a clathrate complex with the trisulfide compound. The cyclodextrin cavity accommodates the hydrophobic portion of the trisulfide molecule while the external hydrophilic surface of cyclodextrin interacts with water, effectively mediating between the insoluble guest molecule and the aqueous environment to enhance solubility and stability.
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 novel trisulfide compounds and their cyclodextrin clathrates exhibit excellent water solubility and stability, addressing limitations in pharmaceutical applications and providing active oxygen- and hydrogen sulfide-eliminating actions.
Implementation Method 1
a cyclodextrin clathrate (hereinafter also referred to as a 'CD clathrate' or simply a 'clathrate') of a trisulfide compound, the cyclodextrin clathrate having excellent water solubility and stability
Data Source
AI summary
A compound represented by Formula (1) or (3).wherein R1 and R2 are each independently a hydrogen atom; a C1-6 alkyl group optionally having one or more substituents selected from the group consisting of a carboxy group and —OR5; a C2-6 alkyl group having one or more substituents selected from the group consisting of —NR6R7 and —N+R9R10R11; or —(CH2CH2O)nR8;wherein R4 is a C1-6 alkyl group having one or more substituents selected from the group consisting of a carboxy group and —OR5; a C2-6 alkyl group having one or more substituents selected from the group consisting of —NR6R7 and —N+R9R10R11, or —(CH2CH2O)nR8;wherein R5, R6, R7, R8, R9, R10 and R11 are each independently a hydrogen atom or a C1-3 alkyl group; and n is an integer of 2 to 5.