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Acid-Labile Acyclic Cucurbit[n]uril Molecular Containers for Controlled Release
Dake Mao1, Yajun Liang2, Yamin Liu1
1Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China.
Angewandte Chemie (International Ed. in English)
|August 17, 2017
Summary
New acid-labile acyclic cucurbiturils (CB[n]) offer controlled drug release. These molecular containers degrade in mildly acidic conditions, enhancing cargo release and cellular uptake for biomedical applications.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Biomedical Engineering
Background:
- Stimuli-responsive molecular containers are crucial for advanced drug delivery systems.
- Traditional cucurbiturils (CB[n]) possess excellent molecular recognition but limited stimuli-responsiveness.
- Developing containers that release cargo under specific physiological conditions remains a key challenge.
Purpose of the Study:
- To introduce novel acid-labile acyclic cucurbituril (CB[n]) molecular containers.
- To investigate their degradation and cargo release kinetics under mildly acidic conditions.
- To evaluate the influence of these containers on cellular uptake of encapsulated cargos.
Main Methods:
- Synthesis and characterization of acid-labile acyclic cucurbituril (CB[n]) derivatives.
- Assessment of cargo release rates at varying pH levels, particularly in the range of pH 5.5-6.5.
- Cell culture studies to quantify cellular uptake of dye cargos complexed with different CB[n] containers.
Main Results:
- The novel acyclic CB[n] containers exhibit acid lability, degrading and releasing encapsulated cargo at accelerated rates under mildly acidic conditions (pH 5.5-6.5).
- These containers maintain the inherent, high-affinity recognition capabilities characteristic of CB[n] hosts.
- Cellular uptake studies demonstrated that the degree of cargo internalization can be modulated by complexing the cargo with different CB[n] variants.
- Acidic pH was shown to significantly promote both cargo release from the containers and subsequent cellular uptake of the released dye.
Conclusions:
- Acid-labile acyclic cucurbiturils represent a promising new class of molecular containers for controlled release applications.
- Their tunable degradation in response to mild acidity allows for precise control over drug release kinetics.
- The ability to fine-tune cellular uptake via complexation opens avenues for targeted drug delivery and enhanced therapeutic efficacy.
