N-Acyl Amino Acid Diol Esters for Endothelial ATP Protection
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Solution Overview
Problem
Current solutions for addressing venous system dysfunction and altered vascular permeability, such as dark circles and heavy legs, primarily focus on masking symptoms rather than treating the underlying causes, and often come with drawbacks like unnatural skin appearance or skin drying.
Innovation Solution
Development of new esters of N-acyl amino acid derivatives and aliphatic diols that prevent the decline in ATP production by endothelial cells under oxidative stress, thereby addressing the root cause of venous system dysfunction and vascular permeability issues.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If new esters of N-acyl amino acid derivatives and aliphatic diols are used to prevent ATP production decline in endothelial cells, then the effectiveness in treating venous system dysfunction is improved, but the complexity of the chemical composition increases
Solution Approach 1:
The patent modifies the chemical structure by changing parameters such as the amino acid type, acyl chain length, and diol structure to optimize the balance between therapeutic effectiveness and structural complexity. Specific embodiments use common amino acids (alanine, valine, leucine, isoleucine, phenylalanine, proline) and standard diols (1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol) to achieve this balance.
Solution Approach 2:
The invention creates composite molecular structures by combining N-acyl amino acid derivatives with aliphatic diols to form ester compounds. This composite approach allows the molecule to simultaneously interact with multiple biological targets (endothelial cells, mitochondria, venous tone receptors) while maintaining a defined chemical structure that can be synthesized and standardized.
2Reliability
If new esters are synthesized to address root cause of venous dysfunction, then the therapeutic benefit is improved, but the manufacturing process complexity increases
Solution Approach 1:
The synthesis process is divided into distinct segments: first synthesizing the N-acyl amino acid derivative intermediate, then reacting it with the aliphatic diol to form the final ester product. This segmentation allows for better control of reaction conditions, easier purification at each stage, and more flexible manufacturing scaling.
Solution Approach 2:
The patent uses well-characterized intermediate compounds (N-acyl amino acid derivatives) that can be independently synthesized and purified before the final esterification step. This intermediary approach simplifies quality control and allows for modular manufacturing where intermediates can be produced in bulk and stored for later conversion to final products.
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 new esters effectively slow down ATP production decline in endothelial cells, reducing unsightly effects like dark circles and heavy legs, without the adverse effects of existing treatments.
Implementation Method 1
Endothelial cells are sensitive to oxidative stress, caused by an increased presence of oxygenated derivatives, such as superoxide ions, hydrogen peroxides, hydroxyl radicals, which exceed the regulatory capacities of the natural antioxidant system
Data Source
AI summary
The invention relates to a compound of formula (I): R'-O-A-O-R'', in which R' and R" are a hydrogen atom or a monovalent radical of formula (IIa), or a monovalent radical of formula (IIb), it being understood that at least one of the radicals R' or R" is not a hydrogen atom and that, when none of the radicals R' and R" is a hydrogen atom, R' and R" are identical, and in which A is a divalent radical of formula (III): -CH(X1)-[C(X2)(X3)]p-CH(X4) in which X1, X2, X3 and X4 are identical or different and are either a hydrogen atom or a methyl radical or an ethyl radical, and p is an integer greater than or equal to 1 and less than or equal to 6. The invention also relates to the method for preparing said compound and to the use thereof in cosmetics and as a drug.