3-Hydroxyflavone CORMs for Metal-Free CO Release
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Solution Overview
Problem
Current carbon monoxide releasing molecules (CORMs) face limitations such as reversibility of CO-release reactions, potential toxicity from metal remnants, low-yield synthetic routes, and challenges in structural modification for tuning physical properties and biological targeting.
Innovation Solution
Development of structurally tunable CORMs based on a 3-hydroxyflavone motif that undergoes visible light-induced CO release, offering high-yield synthesis, solubility in aqueous environments, controllable CO release, low toxicity, and ease of structural modification for improved biocompatibility and tracking within cells.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If metal-based CORMs are used, then CO release can be achieved, but toxicity from metal remnants and reversibility of CO-release reactions occur
Solution Approach 1:
The patent extracts the CO-releasing functionality from metal centers and transfers it to an organic molecular framework based on 3-hydroxyflavone. The organic core undergoes photoinduced decarboxylation to release CO, eliminating metal remnants and their associated toxicity while maintaining controllable CO release through light activation.
Solution Approach 2:
The patent employs an organic molecular design where the CO-releasing unit is a transient, light-activated organic structure rather than a stable metal complex. The 3-hydroxyflavone derivative undergoes irreversible photoinduced decarboxylation to release CO and forms a stable non-toxic product, effectively using a disposable organic molecule instead of a reusable metal complex.
2Reliability
If complex synthetic routes are used for CORMs, then CO release functionality is achieved, but synthesis yield is low and structural modification is difficult
Solution Approach 1:
The 3-hydroxyflavone core serves multiple functions simultaneously: it provides the structural framework for CO release, enables photoinduced activation, allows for easy structural modification through standard organic synthesis, and ensures high synthesis yield through a single-step condensation reaction. The universal applicability of this core structure facilitates both high productivity and functional reliability.
Solution Approach 2:
The patent utilizes parameter changes in the form of substituting different groups at specific positions on the 3-hydroxyflavone core to tune the properties of the CORM. By changing substituents such as electron-withdrawing or electron-donating groups, the photoinduced CO release characteristics, stability, and biological activity can be optimized while maintaining high synthesis yield through the robust condensation reaction.
3Adaptability or versatility
If CORMs are designed for biological targeting, then specificity is improved, but structural complexity increases
Solution Approach 1:
The patent segments the CORM into distinct functional modules: the 3-hydroxyflavone core handles CO release, while separate substituent groups (such as aryl, alkyl, or functionalized groups) provide biological targeting capabilities. This modular segmentation allows independent optimization of CO release functionality and targeting specificity without significantly increasing overall molecular complexity.
Solution Approach 2:
The 3-hydroxyflavone core acts as an intermediary structure that connects the CO-releasing mechanism with biological targeting groups. The core mediates between the photoinduced decarboxylation process and the biological environment, allowing targeting groups to be attached without interfering with the CO release mechanism, thus achieving specificity without excessive complexity.
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 3-hydroxyflavone-based CORMs enable quantitative and controlled CO release with minimal toxicity, allowing for effective tracking and targeting, addressing the limitations of existing CORMs while maintaining stability and biocompatibility.
Implementation Method 1
visible light-induced CO release
Data Source
AI summary
The present disclosure relates to carbon monoxide releasing molecules (“CORMs”), and methods of synthesizing and applying the molecules. More specifically, this disclosure relates to structurally tunable CORMS, compounds containing CORMS (and salts thereof). An exemplary compound includes: