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Azide-Alkyne Click Conjugation on Quantum Dots by Selective Copper Coordination
Victor R Mann1,2, Alexander S Powers1, Drew C Tilley3
1The Molecular Foundry , Lawrence Berkeley National Laboratory , Berkeley , California 94720 , United States.
ACS Nano
|April 3, 2018
Summary
Researchers developed new conditions for copper-catalyzed click reactions on quantum dot (QD) surfaces, preventing fluorescence quenching. This allows for efficient functionalization of QDs for biological imaging applications.
Area of Science:
- Materials Science
- Nanotechnology
- Bioconjugation Chemistry
Background:
- Nanocrystal functionalization is crucial for applications but limited by reagent incompatibility.
- Copper-catalyzed azide-alkyne cycloaddition is a key ligation method, but Cu+ quenches quantum dot (QD) fluorescence.
Purpose of the Study:
- To discover non-quenching synthetic conditions for copper-catalyzed click reactions on QD surfaces.
- To enable efficient and compatible functionalization of semiconductor QDs.
Main Methods:
- Developed a combinatorial fluorescence assay to screen over 2000 reaction conditions.
- Investigated copper coordination and quenching mechanisms.
- Optimized ligand-assisted copper catalysis for QD surface functionalization.
Main Results:
- Identified reaction conditions enabling complete cycloaddition without significant QD fluorescence quenching.
- Demonstrated compatibility with common QD polymer surfaces and diverse azide/alkyne pairs.
- Synthesized unquenched QD-peptidyl toxin conjugates for imaging K+ channels.
Conclusions:
- Superstoichiometric copper concentrations with specific ligands enable efficient, non-quenching click chemistry on QDs.
- This method allows for the creation of functionalized QDs for specific biological targeting and imaging.
- Successfully imaged K+ channel affinity in live cells using QD-peptidyl toxin conjugates.
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