Click Coupling Biomolecules to Substrates with Cyclooctyne N-Heterocyclic Carbenes
The Problem
Biomolecules are frequently appended to metal nanoparticles or surfaces for drug delivery or biosensing. Many approaches have been developed for these applications but generally a linker molecule is required for maximum long-term stability. Conventionally, linkers featuring thiol groups form self-assembled monolayers on substrates but these interactions are not stable long-term and dissociate over time. Biomolecules such as enzymes or aptamers can be attached pre or post-substrate binding and the chemistry often requires catalysts or harsh reaction conditions.
The Solution
Researchers at the University of Tennessee and the University of Notre Dame have developed novel linkers for a wide variety of applications. The key linker feature is the usage of cyclooctyne moieties for attaching a wide variety of functional components equipped with an azide for copper-free click chemistry. This innovation enables a wider suite of potential applications due to the larger availability of azide functionalized biomolecules. The linkers also feature an N-heterocyclic carbene that provides much stronger bonding to metal surfaces compared to thiols. The carbenes can couple to a large variety of substrates in large or nanoparticle formats. These can be purposed for electrochemistry, delivery, or spectroscopic applications based on the substrate format and the linked functional component.
Additional Information:
Benefits
| Benefit |
|---|
| Biomolecules functionalized with azides are widely available and inexpensive |
| Strong substrate binding |
| Applicable to large substrates, microelectrodes, or nanoparticles |
More Information
- Derek Eitzmann
- Assistant Technology Manager, Multi Campus Office
- 865-974-1882 | deitzman@tennessee.edu
- UTRF Reference ID: 24162-03
- Patent Status: Pending
Innovators
David Jenkins
Professor of Chemistry
The Jenkins group focuses on inorganic and organic synthesis to develop chemical systems ranging from homogenous catalysis, to porous frameworks, to surface modifications. We concentrate on three distinct areas of research, all of which are centered around the use of five-membered N-heterocycles (azoles) as ligands for transition metals. The first area is focused on developing macrocyclic tetra N-heterocyclic carbene (NHCs) ligands to stabilize metal-ligand multiple bonds for oxidative group transfer reactions. Typical catalysis studies concentrate on aziridination or epoxidation. In the second area, we utilize triazoles for the development of new metal-organic nanotubes (MONTs). These novel materials are studied on the bulk and nanoscale. The third area employs NHCs as ligands for metal surfaces of nanoparticles. These coated materials have many potential applications in medicine and electronics. To characterize the broad spectrum of compounds and materials that we synthesize, we apply a wide variety of analytical techniques including nuclear magnetic resonance and other spectroscopies, mass spectrometry, porosity measurements, and X-ray diffraction, including both powder and single crystal.
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