Nitrosylated Ascorbic Acid Derivatives for Dual Antioxidant and NO Donor Function
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
Current nitric oxide donor drugs lack the dual functionality of being both antioxidants and avoiding interference with enzymatic processes in the body, which is desirable for enhanced therapeutic effects without disrupting biological functions.
Innovation Solution
Synthesis of NO1-3 derivatives of ascorbic acid through nitrosylation and/or nitration in a buffered solution, producing compounds like 3-nitroso-ascorbic acid and 4-nitroso-ascorbic acid that retain antioxidant properties while avoiding enzymatic substrate or cofactor roles, along with extraction methods from Myrciaria dubia fruit.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If ascorbic acid analogs are designed to act as nitric oxide donors and antioxidants, then therapeutic effectiveness is improved, but the risk of interfering with enzymatic processes increases
Solution Approach 1:
The patent modifies ascorbic acid at specific positions (introducing nitroso or nitro groups at particular locations on the molecular structure) to create localized functional changes that enable nitric oxide donation and antioxidant activity while preserving compatibility with enzymatic processes. This selective modification approach allows the molecule to have different properties at different locations, achieving both therapeutic benefits and biocompatibility.
2Reliability
If existing nitric oxide donor drugs are used, then treatment of cardiovascular and other diseases is achieved, but the dual functionality of antioxidant activity and avoidance of enzymatic interference is lost
Solution Approach 1:
The patent creates ascorbic acid analogs that simultaneously perform multiple functions: they act as nitric oxide donors, maintain antioxidant properties, and avoid interfering with enzymatic processes. This multi-functional design allows a single compound to address multiple therapeutic needs, combining the benefits of nitric oxide donation and antioxidant activity while maintaining biocompatibility.
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 synthesized compounds act as effective nitric oxide donors and antioxidants, potentially treating various ailments without interfering with enzymatic processes, offering enhanced therapeutic benefits.
Implementation Method 1
adding hydrogen peroxide to a stirred solution of ascorbic acid in sodium citrate buffer; adding sodium nitrite peroxide to the stirred solution
Implementation Method 2
derivatizing an ascorbic acid via nitrosylation and/or nitration in a buffered ascorbic acid solution to produce the NO1-3 ascorbic acid derivative
Data Source
AI summary
The present invention relates to methods and strategies for extracting nitrosylated and/or nitrated derivatives and analogs from Myrciaria dubia fruit and for synthesizing the same. The ascorbic acid derivatives and analogs have the chemical structure of:where R1 is ═O, —ONO, —ONO2, or —NH2; R2 is —OH, —ONO, —ONO2, or —NH2; R3 is —OH, —ONO, —ONO2. The extraction method comprises freeze-drying the Myrciaria dubia fruit, mixing the freeze-dried powder with a solvent and separating and drying the supernatant. The synthetic method comprises derivatizing an ascorbic acid via nitrosylation and/or nitration in a buffered ascorbic acid solution, reducing zero or more nitro groups to an amine group, and purifying the ascorbic acid analog.