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Stimuli responsive systems constructed using cucurbit[n]uril-type molecular containers.

Lyle Isaacs1

  • 1Department of Chemistry and Biochemistry, University of Maryland , College Park, Maryland 20742, United States.

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Summary
This summary is machine-generated.

Cucurbit[n]urils (CB[n]) act as molecular containers in water, enabling stimuli-responsive systems. These CB[n] receptors demonstrate high binding affinity and selectivity, driving conformational changes and regulating biological processes for drug delivery and therapeutic applications.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Chemical Biology

Background:

  • Self-sorting phenomena in molecular assemblies are driven by non-covalent interactions.
  • Cucurbit[n]urils (CB[n]) are macrocyclic hosts with exceptional binding affinities and selectivities in aqueous solutions.
  • Previous work established the high selectivity of H-bonded assemblies and self-sorting behavior.

Purpose of the Study:

  • To explore the application of cucurbit[n]urils (CB[n]) in constructing stimuli-responsive systems in water.
  • To investigate the use of CB[n] host-guest chemistry for driving conformational changes and regulating molecular processes.
  • To evaluate the potential of CB[n]-based systems in biological applications, including drug delivery and therapeutic interventions.

Main Methods:

  • Utilizing cucurbit[n]urils (CB[n]) as key recognition elements in aqueous supramolecular systems.
  • Employing host-guest complexation of CB[n] with guests like adamantaneammonium ion to trigger responses.
  • Investigating conformational changes in guests and hosts induced by CB[n] complexation.
  • Assessing CB[n] receptor performance in biological assays, including enzyme inhibition and drug delivery models.

Main Results:

  • CB[n] homologues (CB[7], CB[8]) exhibit high binding affinities (up to 10^17 M^-1) and selectivities for guests.
  • Host-guest complexation drives conformational changes in foldamers, calixarenes, and CB[n] hosts, including allostery and dimerization.
  • Significant pKa shifts in CB[n]-guest complexes enable pH-controlled guest swapping and isomerization.
  • CB[n] systems demonstrate stimuli-responsive enzyme inhibition and intracellular sequestration of nanoparticles.
  • Acyclic CB[n] receptors act as solubilizing agents for insoluble drugs and as reversal agents for neuromuscular blockers in vivo.

Conclusions:

  • CB[n] molecular containers are versatile platforms for designing sophisticated stimuli-responsive systems in aqueous media.
  • The high affinity and selectivity of CB[n] enable precise control over molecular and conformational changes.
  • CB[n]-based receptors show significant promise for advanced applications in chemical biology, drug delivery, and therapeutics.