Phytosterol Nitroderivatives Phosphate Linker Solubility
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Solution Overview
Problem
Current phytosterol and phytostanol derivatives face challenges in therapeutic efficacy due to their hydrophobic nature, which complicates their administration and incorporation into pharmaceuticals for treating cardiovascular diseases and other conditions.
Innovation Solution
Development of novel phytosterol and phytostanol nitroderivatives with a nitro group linked via a phosphate moiety, enhancing their solubility and therapeutic profile, allowing for effective incorporation into pharmaceutical compositions for treating cardiovascular diseases and related conditions.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If phytosterols and phytostanols are used to treat cardiovascular diseases, then therapeutic efficacy is improved, but their hydrophobic nature causes poor water solubility which complicates administration and incorporation into pharmaceuticals
Solution Approach 1:
The patent applies parameter changes by chemically modifying the phytosterol and phytostanol molecules by introducing a phosphate group at the 3-beta position. This chemical modification fundamentally changes the solubility parameter of the compound, transforming it from hydrophobic to highly water-soluble, while preserving the therapeutic efficacy of the original sterol structure
Solution Approach 2:
The invention creates a composite molecular structure by combining the sterol core (responsible for therapeutic efficacy) with a phosphate group (responsible for water solubility). This composite approach allows the single molecule to simultaneously provide both cholesterol-lowering activity and enhanced aqueous solubility for easier pharmaceutical formulation and administration
2Reliability
If phytosterols are administered to lower serum cholesterol, then cardiovascular disease risk is reduced, but their hydrophobicity limits their incorporation into pharmaceutical delivery systems
Solution Approach 1:
The phosphate modification fundamentally changes the physical-chemical parameters of the phytosterol, specifically transforming its solubility characteristics from hydrophobic to hydrophilic. This enables straightforward incorporation into aqueous pharmaceutical formulations, injection vehicles, and various delivery matrices that would be inaccessible to the original hydrophobic compounds
Solution Approach 2:
The phosphate group acts as an intermediary that bridges the sterol core and the aqueous pharmaceutical environment. This intermediary group provides the necessary hydrophilic character to facilitate incorporation into pharmaceutical delivery systems while leaving the sterol core intact to maintain its cholesterol-lowering mechanism of action
Data Source
AI summary
Sterol and stanol phosphorylnitro derivatives and their use in treating or preventing cardiovascular disease, its underlying conditions and other disorders are disclosed. The disclosed compounds include a phosphate linker, at least one moiety that releases nitric oxide (NO), and a sterol or stanol moiety. Some compounds additionally include an ascorbyl moiety to make the compound more readily soluble in aqueous and non-aqueous media.