Low-Substitution Methylated Cyclodextrin for Lipophilic Solubilization
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Solution Overview
Problem
Lowly methylated cyclodextrins have a limited capacity to solubilize lipophilic compounds, which is a contradiction to their pharmacological activity on lipid metabolism, requiring a balance between pharmacological effectiveness and solubilization ability.
Innovation Solution
A methylated cyclodextrin with a low degree of molar substitution (MS) between 0.05 and 1.50, characterized by reduced conductivity when in aqueous solution, is developed through a process involving etherification and ion species reduction, enhancing its solubilization capacity while maintaining pharmacological activity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If the degree of molar substitution (MS) of methyl cyclodextrin is kept low (between 0.05 and 1.50) to maintain pharmacological activity on lipid metabolism, then the pharmacological effectiveness is improved, but the capacity to solubilize lipophilic compounds deteriorates
Solution Approach 1:
The invention changes the physical-chemical parameters of methyl cyclodextrin by controlling the degree of molar substitution within a specific range (0.05-1.50) and adjusting the molar ratio of cyclodextrin to methanol during synthesis. This parameter optimization allows the product to simultaneously achieve sufficient pharmacological activity and adequate solubilization capacity, resolving the contradiction between these two opposing requirements
2Quantity of substance
If highly methylated cyclodextrins are used to improve solubilization capacity, then the solubilization ability is improved, but the pharmacological activity on lipid metabolism deteriorates
Solution Approach 1:
The invention establishes a specific parameter range for the degree of molar substitution (0.05-1.50) that prevents excessive methylation. This controlled parameter change ensures that the cyclodextrin maintains its pharmacological activity while achieving sufficient solubilization capacity, avoiding the harmful effects of high methylation
3Ease of manufacture
If conventional etherification process is used for methyl cyclodextrin preparation, then the manufacturing process is simple, but the ionic species content is high resulting in poor solubilization performance
Solution Approach 1:
The invention extracts and removes ionic species from the methyl cyclodextrin preparation process by controlling the etherification conditions and implementing purification steps. This extraction of harmful ionic components enables the product to achieve better solubilization performance while maintaining manufacturing simplicity
Solution Approach 2:
The invention changes the process parameters of etherification by controlling the molar ratio of cyclodextrin to methanol and adjusting reaction conditions. These parameter changes reduce ionic species formation during synthesis, improving solubilization capacity without significantly complicating the manufacturing process
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 resulting methylated cyclodextrin effectively solubilizes lipophilic compounds, improving their chemical stability, delivery through biological membranes, and physical stability, and is suitable for pharmaceutical compositions treating type 2 diabetes and related conditions.
Implementation Method 1
Cyclodextrins having a hydrophilic exterior part and a hydrophobic cavity are generally used for their capacity to encapsulate lipophilic compounds or groups
Implementation Method 2
The interior of the cone or the cavity of cyclodextrins is made up of the hydrogen atoms carried by the C 3 and C 5 carbons as well as the oxygen atoms participating in the glycosidic bond, thus giving them a nonpolar character
Implementation Method 3
The Applicant has shown in particular that these low MS methyl-cyclodextrins were capable of acting effectively and specifically on lipid metabolism
Data Source
Figure 1
AI summary
The invention relates to a novel methylated cyclodextrin and to a novel method used for the production thereof. The invention also relates to the use of said methylated cyclodextrin for the solubilisation of lipophilic compounds, or carriers of at least one lipophilic group. The invention further relates to a composition comprising said methylated cyclodextrin, particularly a pharmaceutical composition.