Cucurbit[n]uril-based amphiphiles that self-assemble into functional nanomaterials for therapeutics

Abstract

In this feature article, the two types (molecular amphiphile and supramolecular amphiphile) of CB-based amphiphiles, their self-assemblies and their applications for useful nanotherapeutics and theranostics are presented with future perspectives.

pH/ROS Dual-Responsive Supramolecular Vesicles Fabricated by Carboxylated Pillar[6]arene-Based Host–Guest Recognition and Phenylboronic Acid Pinacol Ester Derivative

“…Among the various noncovalent interactions employed to fabricate supra-amphiphiles, host–guest interactions have attracted considerable interest because of their designability and strong complexation. , The emergence of various macrocycles, such as crown ethers, cyclodextrins, calix­[ n ]­arene, cucurbit­[ n ]­uril, and pillar­[ n ]­arene, has promoted the development of supra-amphiphiles formed with intriguing host–guest binding motifs. − Among these macrocycles, pillar­[ n ]­arene is a kind of distinctive host on account of its good solubility and readily functionalizable nature. , The past few years have witnessed a boom in constructing stimuli-responsive supra-amphiphiles and self-assemblies involved in pillar­[ n ]­arene as building blocks. − The development of novel multiple-stimuli-responsive systems through a novel recognition motif is of significant interest and still desired.…”

Simultaneous analyte indicator binding assay (SBA) for the monitoring of reversible host–guest complexation kinetics

“…in molecular devices, drug delivery vehicles, stimuli-responsive materials, functional nanostructures, and supramolecular polymeric hydrogels. [1][2][3][4][5][6][7][8] The understanding of the major factors influencing the rate constants of association and dissociation is crucial also for the application of cavitands in the biomedical field, 9 catalysis, 10,11 and self-sorting multicomponent systems. 12,13 Time-resolved measurements provide insights into the subtle mechanistic details of the inclusion of simple 14,15 and ditopic guests [16][17][18] as well as those of the cationinduced release of encapsulated molecules.…”

Alkyl-Substituted Cucurbit[6]uril Bridged β-Cyclodextrin Dimer Mediated Intramolecular FRET Behavior

“…The residue was purified by column chromatography (silica gel, petroleum ether/CH 2 Cl 2 = 1:2, v/v) to give compound 1 as a white powder (2.42 g, 95% yield). 1 H NMR (400 MHz, DMSOd 6 , TMS): δ1.66 (m, 6H, H of adamantane), 1.82 (m, 6H, H of adamantane), 1.98 (s, 3H, H of adamantane), 4.98 (s, 2H, H of CH 2 ), 6.60−6.62 (d, J = 8 Hz, 2H, H of benzene), 6.82−6.84 (d, J = 8 Hz, 2H, H of benzene) 6.93−7.18 (m, 14H, H of benzene); 13 Preparation of Compound 3. To a solution of 2 16 (30 mg, 0.027 mmol) and N,N′-dihexylviologen bromide salt (13.10 mg, 0.027 mmol), in anhydrous DMSO (2 mL), NaH (10 mg, 0.4 mmol) was added and stirred at room temperature for 15 min.…”

“…The introduction of functional groups on skeletons of CB­[ n ]­s has been a huge challenge in CB­[ n ] chemistry due to the chemical stability of CB­[ n ]­s. In 2003, Kim and co-workers first prepared a series of CB­[ n ] derivatives, hydroxy-substituted (HO) 2 n CB­[ n ]­s, by simple oxidation of the native CB­[ n ]­s with K 2 S 2 O 8 in water, and this served as an accelerator for the application of functionalized CB­[ n ]­s in vesicles, polymers, nanomaterials, artificial ion channels, and so on. − However, the yields for alkyl-substituted CB­[ n ]­s in this method was too low for practical use. In 2016, Bardelang and Ouari reported a photochemical method by UV and hydrogen peroxide to introduce a limited number of alcohol functional groups on CB­[ n ]­s ( n = 5, 6, 7, and 8) .…”