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Designing Functional and Responsive Molecules with Boronic Acids.
João P M António1, Inês L Roque1, Fábio M F Santos1
1Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, 1649-003 Lisbon, Portugal.
Boronic acids (BAs) are versatile building blocks for functional materials, enabling reversible covalent bonds. Their unique reactivity with stimuli like ROS allows for the development of disease-responsive materials for potential therapeutic applications.
Area of Science:
- Organic Chemistry
- Materials Science
- Medicinal Chemistry
Background:
- Boronic acids (BAs) are crucial reagents in synthesis, forming key carbon-carbon and carbon-heteroatom bonds.
- Their potential as building blocks for functional molecules is often underestimated.
- BAs form reversible covalent bonds via interconversion between trigonal planar and sp3-hybridized forms.
Purpose of the Study:
- To explore the potential of boronic acids in designing functional materials.
- To focus on the response of different boron complexes to biologically relevant stimuli.
- To provide an overview of BA-enabled mechanisms for designing materials with therapeutic potential.
Main Methods:
- Investigated the coordination chemistry of boronic acids.
- Studied the oxidation of BAs in the presence of reactive oxygen species (ROS).
- Described the preparation and stimulus-response of boronated esters, BA-salicylhydroxamic acid complexes, iminoboronates, diazaborines, and boronated thiazolidines.
Main Results:
- Boronic acids enable the creation of diverse materials, including drugs, bioconjugates, and sensors.
- Functionalization of the BA coordination sphere allows for structural diversity and stimuli-responsive mechanisms.
- Specific boron chemotypes respond to disease-relevant triggers like pH, carbohydrates, glutathione, and hydrogen peroxide.
Conclusions:
- Understanding BA dynamic mechanisms allows engineering of sophisticated, stimuli-responsive materials.
- These materials can respond to disease indicators, offering potential for innovative therapeutic options.
- Boronic acids are at the forefront of designing materials to influence disease mechanisms.
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