Stimuli-responsive mechanically interlocked molecules constructed from cucurbit[<i>n</i>]uril homologues and derivatives

Liu, Jingxin; Chen, Kai; Redshaw, Carl

doi:10.1039/d2cs00785a

Cited by 65 publications

(12 citation statements)

References 179 publications

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“…Nowadays, most of the existing reviews related to rotaxanes and polyrotaxanes focus on the precise synthesis of mechanically interlocked molecules and the control of microscopic molecular shuttles to extend the scope of molecular machines. [ 36‐43 ] In terms of functional materials, the relationship between the fascinating pulley effect and high mechanical performance should be emphasized. Meanwhile, the diversity of material usage requirements in practical applications places high demands on the functional adaptability of slide‐ring structures.…”

Section: Introductionmentioning

confidence: 99%

Polyrotaxane‐Based Functional Materials Enabled by Molecular Mobility and Conformational Transition^†

Cui

Zhang

2023

Chin. J. Chem.

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Comprehensive SummarySlide‐ring structured polyrotaxanes with high molecular mobility and reversible conformational transition ability can achieve high performance and multifunctionality of the material in various applications. There have been many reviews describing advances in the research of rotaxanes and polyrotaxanes. However, most of them typically focus on the precise synthesis of mechanically interlocked molecules and the control of microscopic molecular shuttles. In this review, we examine the effects of motion activity and conformational transition due to molecular slide on the performance of polyrotaxanes and the latest functional applications. Different designs of polyrotaxane‐based functional materials are presented to improve the potential for applications including self‐healing stretchable elastomers/gels, stimuli‐responsive smart devices, battery electrode binders, and biomedical drug delivery. It is anticipated that this review will provide insights and guidance for future developments in the design, synthesis and application of polyrotaxane‐based functional materials.

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Section: Introductionmentioning

confidence: 99%

Polyrotaxane‐Based Functional Materials Enabled by Molecular Mobility and Conformational Transition^†

Cui

Zhang

2023

Chin. J. Chem.

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“…Collectively, these data unfold the factors that biomedical researchers need to consider (among others) to get more efficient drug delivery systems in cancer therapy that involve a macromolecular system or other drug vehicles. Specifically, the present work offers a new supramolecular architecture that utilizes the unique properties of the 4,4′-bipyridine unit, which follows the most recent current literature 40,41 in the context of their prospect implications on developing stimuli-responsive hydrogels in biomedicine, exploring and promoting more applications of smart materials in practical production.…”

Section: Supramolecular Effects On Cellular Internalization (Role Of ...mentioning

confidence: 95%

Alginate supramolecular hydrogels based on viologen and cucurbit[8]uril: Host‐induced caveolae‐mediated endocytosis to white blood cancer cells

Chandra,

Bykova,

Poulose

et al. 2023

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The cellular uptake of drug carriers to the cytosol of a specific cell remains challenging, and a non‐classical supramolecular strategy is motivated. Here, we select a model host–guest complex in which a diamino‐viologen (1,1′‐bis(4‐aminophenyl)‐[4,4′‐bipyridine]−1,1′‐diium dichloride [VG]) fluorescent tag was engulfed by cucurbit[8]uril (CB8) and covalently linked to alginate polysaccharides (alginic acid [ALG]) as the modified drug vehicle. When adsorbed on the ALG surface, the encapsulation of VG was first confirmed utilizing Fourier transform infrared and nuclear magnetic resonance spectroscopic methods. Solid optical measurements (diffuse reflectance spectroscopy, photoluminescence, and time‐resolved photoluminescence) revealed emissive materials at around 650 nm and that CB8 enhanced the rigidity of the modified hydrogel. The molar composition of 2:1 for the complexation of VG to CB8 on the alginate surface and the thermal stabilities were also confirmed using thermogravimetric analysis and differential scanning calorimetry techniques. CB8 induced a dramatic decrease in the average size of the VGALG polysaccharides from 485 to 165 nm and a turnover in their charge from –19.8 to +14.4 mV. Flow cytometry with inhibitors of various endocytosis pathways was employed to track the cellular uptake across different blood cell types: human T‐cell leukemia 1301 and peripheral blood mononuclear cells. Noticeably, complexation of VG with the CB8 host on top of the sugar platform dramatically enhanced the internalization into 1301 cells (viz. from 1% to 99%) at a concentration of 1.8 mg/mL via caveolae‐mediated endocytosis because of the size reduction, turnover in the charge from negative to positive, and rigidity induction. These observations reveal a more profound understanding of the macrocyclic effects on drug delivery.

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“…Mechanically interlocked molecules have attracted significant interest due to their fascinating topological structure and unique functions. 46 Liu and coworkers designed a series of mechanically self-locked molecules by condensing P[5]-dicarboxylic acid and α, ω-diamine (Fig. 11a).…”

Section: Mechanically Self-locked Macrocyclic Arenesmentioning

confidence: 99%

Chiroptical regulation of macrocyclic arenes with flipping-induced inversion of planar chirality

Zhao,

Wu,

Yang

2023

Chem. Commun.

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Stimuli-responsive mechanically interlocked molecules constructed from cucurbit[n]uril homologues and derivatives

Abstract: This review covers the important advances in the field of cucurbit[n]uril-based mechanically interlocked molecules over the past two decades.

Cited by 65 publications

References 179 publications

Polyrotaxane‐Based Functional Materials Enabled by Molecular Mobility and Conformational Transition^†

Polyrotaxane‐Based Functional Materials Enabled by Molecular Mobility and Conformational Transition^†

Alginate supramolecular hydrogels based on viologen and cucurbit[8]uril: Host‐induced caveolae‐mediated endocytosis to white blood cancer cells

Chiroptical regulation of macrocyclic arenes with flipping-induced inversion of planar chirality

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Stimuli-responsive mechanically interlocked molecules constructed from cucurbit[n]uril homologues and derivatives

Abstract: This review covers the important advances in the field of cucurbit[n]uril-based mechanically interlocked molecules over the past two decades.

Cited by 65 publications

References 179 publications

Polyrotaxane‐Based Functional Materials Enabled by Molecular Mobility and Conformational Transition†

Polyrotaxane‐Based Functional Materials Enabled by Molecular Mobility and Conformational Transition†

Alginate supramolecular hydrogels based on viologen and cucurbit[8]uril: Host‐induced caveolae‐mediated endocytosis to white blood cancer cells

Chiroptical regulation of macrocyclic arenes with flipping-induced inversion of planar chirality

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Product

Resources

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Polyrotaxane‐Based Functional Materials Enabled by Molecular Mobility and Conformational Transition^†

Polyrotaxane‐Based Functional Materials Enabled by Molecular Mobility and Conformational Transition^†