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Cucurbituril chemistry: a tale of supramolecular success

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TLDR
Cucurbit[n]urils have become key units in various self-organizing and stimulus-controlled assemblies, as well as in advanced materials and drug carriers.
Abstract
This review highlights the past six year advances in the blossoming field of cucurbit[n]uril chemistry. Because of their exceptional recognition properties in aqueous medium, these pumpkin-shaped macrocycles have been generating some tremendous interest in the supramolecular community. They have also become key units in various self-organizing and stimulus-controlled assemblies, as well as in advanced materials and drug carriers. The scope of this review is limited to the main family of cucurbit[n]urils (n = 5, 6, 7, 8, 10). The reader will find an overview of their preparation, their physicochemical and biological properties, as well as their recognition abilities towards various organic and inorganic guests. Detailed thermodynamic and kinetic considerations, as well as multiple applications including supramolecular catalysis are also discussed.

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Journal ArticleDOI

From Packed "Sandwich" to "Russian Doll": Assembly by Charge-Transfer Interactions in Cucurbit[10]uril.

TL;DR: The recognition properties of CB[10] are presented toward a series of bipyridinium guests including the tetracationic cyclophane known as blue box along with electron-rich guests and the influence of encapsulation on the charge-transfer interactions between guests is detailed.
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Cucurbit[6]uril-Promoted Click Chemistry for Protein Modification

TL;DR: It is demonstrated that CB6 click can be used in conjunction with strain-promoted azide-alkyne cycloaddition to generate distinct bioconjugates in protein mixtures and is a promising new reaction for the development of protein conjugates.
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Acyclic CB[n]-type molecular containers: effect of solubilizing group on their function as solubilizing excipients

TL;DR: It is shown that the weaker binding affinities measured for neutral and positively charged hosts 2h and 2f compared to anionic 2a results in a decreased ability to act as solubilizing agents for either cationic, neutral, or anionic drugs in water.
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Molecular Containers Bind Drugs of Abuse in Vitro and Reverse the Hyperlocomotive Effect of Methamphetamine in Rats

TL;DR: The bioavailability of the calabadions and their convergent building block synthesis suggest potential for further structural optimization as reversal agents for intoxication with nonopioid drugs of abuse for which no treatments are currently available.
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Cucurbituril-Based Biomacromolecular Assemblies.

TL;DR: This minireview focuses on the impressive advances in CB-based biomacromolecular assemblies, such as biosensors and assays, the regulation of biochemical reactions, and the treatment of serious diseases.
References
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Journal ArticleDOI

The cucurbit[n]uril family

TL;DR: In 1981, the macrocyclic methylene-bridged glycoluril hexamer (CB[6]) was dubbed "cucurbituril" by Mock and co-workers because of its resemblance to the most prominent member of the cucurbitaceae family of plants--the pumpkin.
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Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry.

TL;DR: This Account is a compilation of recent literature covering the syntheses of the homologues and derivatives, and their supramolecular chemistry of cucurbituril, a synthetic receptor.
Journal ArticleDOI

Nanotechnology in Drug Delivery and Tissue Engineering: From Discovery to Applications

TL;DR: Two important aspects of nanomedicine, drug delivery and tissue engineering are discussed, highlighting the advances the authors have recently experienced, the challenges they are currently facing, and what they are likely to witness in the near future.
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