![Quantitative SERS Detection of Uric Acid via Formation of Precise Plasmonic Nanojunctions within Aggregates of Gold Nanoparticles and Cucurbit[n]uril](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F61682.jpg&w=3840&q=50)
Host-guest complexation between cucurbit[7]uril and doxepin induced supramolecular assembly
1Department of Chemistry, Faculty of Science, Al-Balqa Applied University, Al-Salt 19117, Jordan. Khaleel.assaf@bau.edu.jo.
Organic & Biomolecular Chemistry
|July 14, 2022
Summary
Doxepin (DOX) forms a host-guest complex with cucurbit[7]uril (CB7) in water. This supramolecular assembly, confirmed by NMR and DLS, shows potential for drug delivery applications.
Area of Science:
- Supramolecular Chemistry
- Chemical Biology
- Materials Science
Background:
- Doxepin (DOX) is a tricyclic antidepressant with limited aqueous solubility.
- Cucurbit[7]uril (CB7) is a macrocyclic host known for its ability to form inclusion complexes with various guest molecules.
- Understanding host-guest interactions is crucial for developing novel drug delivery systems.
Purpose of the Study:
- To investigate the supramolecular complexation of doxepin (DOX) with cucurbit[7]uril (CB7) in aqueous solution.
- To characterize the binding affinity and structural features of the DOX-CB7 complex.
- To explore the potential for DOX-CB7 complex formation to induce supramolecular assembly.
Main Methods:
- Nuclear Magnetic Resonance (NMR) spectroscopy to observe complexation-induced chemical shifts.
- Quantum-chemical calculations to support structural interpretations.
- Isothermal Titration Calorimetry (ITC) and dye-displacement assays to determine binding affinity.
- Dynamic Light Scattering (DLS) to analyze the size and distribution of supramolecular assemblies.
Main Results:
- Evidence of host-guest complex formation between DOX and CB7, with the alkylammonium tail of DOX encapsulated within the CB7 cavity.
- Moderate binding affinity (10^4 M^-1) was determined for the DOX-CB7 complex.
- Partial encapsulation of DOX by CB7 induced the formation of supramolecular assemblies at millimolar concentrations.
- DLS measurements confirmed homogeneous size distributions of the assemblies with an average diameter of 1700 nm.
Conclusions:
- Doxepin (DOX) forms a stable supramolecular complex with cucurbit[7]uril (CB7) in aqueous solution.
- The DOX-CB7 complex exhibits a defined binding mode and moderate affinity.
- The formation of supramolecular assemblies driven by DOX-CB7 complexation suggests potential applications in drug formulation and delivery.
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