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Soft Matter · 2019 ·Vol. 15 ·期 47 ·9797-9804 · IF 3.399

Dual-cross-linked dynamic hydrogels with cucurbit[8]uril and imine linkages

Jin Zhang,Shengzhen Hou,Yanru Chen,Jing Zhou,Hao Chen,Yebang Tan

The strategy of dual cross-linking was investigated by enhancing the performance of dynamic hydrogels. To this end, phenylalanine modified ε-polylysine was synthesized and employed as the polymer backbone of hydrogels. The phenylalanine moieties and amine groups of the polymer could be cross-linked with cucurbit[8]uril (CB[8]) and the dialdehyde cross-linker, respectively. Single CB[8] linkage with fast dynamics led to an increase in the viscosity of the polymer solution, and single imine linkage with slow dynamics led to the formation of weak and brittle hydrogels. However, the two linkages were combined together to form a dual-cross-linked hydrogel and the performance of the hydrogel could be well enhanced. Compared with the single imine cross-linked hydrogel, the dual-cross-linked hydrogel demonstrated a higher mechanical strength, better extensibility and faster self-healing rate. It is anticipated that this line of research could provide a useful method to enhance the performance of dynamic hydrogels.

CAS / MDL: 3674-06-4 25322-68-3
研究领域: 材料科学 · 生物化学
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AUSTRALIAN JOURNAL OF CHEMISTRY · 2019 ·Vol. 72 ·期 7 ·533-541 · IF 1.226

Trans-4-[4-(dimethylamino)styryl]-1-methylpyridinium Iodide@Hemimethylcucurbit[6]uril Fluorescent Probe for Anion Recognition

Sai Huang,Mei Yang,Xin-Yu Deng,Qian Jiang Zhu,Ying Huang,Zhu Tao,Kai Chen

In the present work, a host–guest system of a hemimethyl-substituted cucurbit[6]uril derived from 3α-methyl-glycoluril (HMeQ[6]) and a hemicyanine dye, trans-4-[4-(dimethylamino)styryl]-1-methylpyridinium iodide (t-DSMI) showing strong fluorescence emission has been evaluated as a fluorescent probe. The results of a preliminary systematic study on the detection of a series of inorganic anions have revealed that this Q[n]-based host–guest fluorescent probe shows clear responses to BF4− and H2PO4− anions through distinct fluorescence quenching. Application of this Q[n]-based host–guest interaction system in anion recognition or detection opens a new avenue in Q[n] chemistry.

CAS / MDL: 7631-99-4
研究领域: 化学 · 分析化学
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MICROCHIMICA ACTA · 2019 ·Vol. 186 ·期 8 ·1-8 · IF 5.479

Magnetic cucurbit[6]uril-based hypercrosslinked polymers for efficient enrichment of ubiquitin

Jiang Dandan,Li Zheng,Jia Qiong

The design and preparation of magnetic cucurbit[6]uril hypercrosslinked with polymers are described. The materials have a large specific surface, abundant mesopores and cavities, and display superparamagnetism. They were applied to the enrichment of ubiquitinated peptides from standard protein digests. Following desorption with 0.15% TFA, the peptides were quantified by MALDI-TOF MS. The method has a detection limit of 2 fmol·μL −1 and a mass ratio selectivity of 1:5000 as shown for ubiquitin and bovine serum albumin. The materials enable selective capture of ubiquitinated peptides from genuine samples comprising of oyster mushroom and human serum. This demonstrates their potential for the analysis of low-level ubiquitin in complex samples. Schematic presentation for the synthesis of magnetic cucurbit[6]urils hypercrosslinked polymers (MagCB[6]-HCPs).

研究领域: 生物化学 · 分析化学
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ACS Omega · 2023 · IF 4.1

Supramolecular Assembly of Tetramethylcucurbit[6]uril and 2-Picolylamine

Ying Fan,Ran Cen,Peihui Shan,Carl Redshaw,Hang Cong,Xin Xiao,Qingmei Ge

The supramolecular assembly of symmetrical tetramethylcucurbit[6]uril (TMeQ[6]) and 2-picolylamine (AMPy) has been investigated via various techniques, including ultraviolet–visible (UV–vis) and nuclear magnetic resonance spectroscopy, isothermal titration calorimetry (ITC), and X-ray crystallography. The results indicated that TMeQ[6] could encapsulate the AMPy guest molecule to form a stable inclusion complex. The rotational restriction of the guest in the cavity of TMeQ[6] resulted in a large negative value of entropy. The X-ray crystal structure of the 1:1 inclusion complex between TMeQ[6] and AMPy revealed that AMPy exists in the elliptical cavity of TMeQ[6].

CAS / MDL: 61-19-8
研究领域: 化学 · 材料科学
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Journal of Cleaner Production · 2024 · IF 9.7

Supramolecular porous phase change materials for encapsulation of nitrate with amino-expanded graphite by cucurbit[7]uril

Jingxin Kang,Huihui Wang,Changjun Zou,Yuqin Li,Jianwei You,Enxing Liu,Wenyue Tang,Yezhong Wang,Bo Wen,Yixuan Cao

The demand for oil and natural gas energy is increasing dramatically, and the extraction of conventional oil and gas reservoirs is in a stage of exhaustion. In order to stabilize the functionalized properties of oil-based drilling fluids (OBDF) during the extraction of oil and gas reservoirs in ultra-deep wells, the present experiments were carried out on the material (EG-NIT/CB[7]) obtained by encapsulating nitrate (NIT) in expanded graphite (EG) with porous structure through the supramolecular self-assembly property of cucurbit[7]uril (CB[7]). The structural properties were analyzed using various analytical tools and the results showed that our material synthesis was successful. And the effect of mass fraction of EG, CB[7] on the heat transfer and storage of EG-NIT and EG-NIT/CB[7] materials was investigated. The increase in mass fraction of EG can increase the thermal conductivity of EG-NIT up to 7.4 times and the introduction of CB[7] further improves the thermal conductivity of EG-NIT/CB[7] by up to 1.38 W/m·k. The latent heat value of EG-NIT/CB[7] decreased by only 4.7% after 200 cycles. Meanwhile, under the condition of 150 °C, adding EG-NIT/CB[7] to drilling fluids can reduce the temperature of drilling fluids by 2.8 °C. And it improves the stability of drilling fluids, the viscosity almost does not change, and it can also play a certain role in inhibiting the leakage of drilling fluids. Therefore, the EG-NIT/CB[7] developed by us can be practically applied in ultra-deep drilling projects.

研究领域: 材料科学 · 能源工程
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EUROPEAN JOURNAL OF INORGANIC CHEMISTRY · 2019 ·Vol. 2019 ·期 9 ·1212-1219 · IF 2.578

Recognition of Different Metal Cations by a trans-4-[4-(Dimethylamino)styryl]-1-methylpyridinium Iodide@Tetramethylcucurbit[6]uril Probe

Xin Yu Deng,Kai Chen,Ming-Dong Chen,Li Bin Lü,Zhu Tao

Graphical The probe responds to Cs + cations in alkali metal systems, Ba 2+ and Sr 2+ cations in alkaline earth metal systems; Eu 3+ , Tm 3+ , and Yb 3+ cations in lanthanide systems, and Cr 3+ , Fe 3+ , and Hg 2+ cations in systems containing transition and other metal cations, by obvious fluorescence quenching. Based on the study of a known host–guest inclusion complex comprising cucurbit[6]uril (Q[6]) and a hemicyanine dye, trans -4-[4-(dimethylamino)styryl]-1-pyridinium iodide ( t -DSMI), a water-soluble symmetric tetramethylcucurbit[6]uril (TMeQ[6]), was selected to construct a t -DSMI-based probe to test the response to various metal cations in neutral water. The experimental results revealed that the probe responded to Cs + cations in alkali metal systems, Ba 2+ and Sr 2+ cations in alkaline earth metal systems, Eu 3+ , Tm 3+ and Yb 3+ cations in lanthanide systems, and Cr 3+ , Fe 3+ and Hg 2+ cations in systems containing transition and other metal cations, via obvious fluorescence quenching.

研究领域: 化学 · 分析化学
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DYES AND PIGMENTS · 2021 · IF 4.889

Supramolecular tandem assay for tyrosinase based on cucurbit[8]uril induced peptide inclusion

Yong-Qi Cai,Gao Li

Many fluorometric methods have been developed for detecting tyrosinase activity, yet many of them require the sophisticated synthesis of relatively complex fluorescent molecules. Here, we report the utilization of a label-free supramolecular tandem assay for measuring tyrosinase activity based on an easily available reporter pair. Cucurbit[8]uril (CB[8]) can bind with thioflavin-T (ThT) and increase its fluorescence intensity , while the tripeptides YLA and Dopa-LA can decrease the fluorescence intensity of CB[8]-ThT complex. YLA and Dopa-LA can be oxidized by tyrosinase, and the products have lower binding affinity with CB[8], leading to an increase of fluorescence in the intensity of CB[8]-ThT-YLA or Dopa-LA. We were able to continuously monitor tyrosinase activity with CB[8]-ThT-YLA or Dopa-LA.

研究领域: 生物化学 · 分析化学
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MICROCHIMICA ACTA · 2019 ·Vol. 187 ·期 1 ·1-12 · IF 5.479

A polymer monolith composed of a perovskite and cucurbit[6]uril hybrid for highly selective enrichment of phosphopeptides prior to mass spectrometric analysis

Zheng Haijiao,Jia Qiong

A hybrid monolith was prepared from perovskite and cucurbit[6]uril [poly(hydroxyethyl methacrylate-pentaerythritol triacrylate) monolith] for the enrichment of phosphopeptides. By coupling with mass spectrometry, three goals were simultaneously realized, viz. (a) selective enrichment of phosphopeptides from non-phosphopeptides, (b) identification of mono- and multi-phosphopeptides, and (c) recognition of tyrosine phosphopeptides. The perovskite introduced into the monolith warrants high selectivity for phosphopeptides even at a high (10,000:1) ratio of non-phosphopeptides to phosphopeptides, and and enables identification of eight mono- and multi-phosphopeptides from standard β-casein tryptic digests. Tyrosine phosphopeptides were specifically detected via the recognition capability of cucurbit[6]uril integrated into the monolith. The method has remarkably specific enrichment capacity for phosphopeptides from samples including human serum, nonfat milk, and human acute myelocytic leukemia cell lysate. Schematic representation of a monolith integrated with perovskite and cucurbit[6]uril. The monolithic column was coupled with mass spectrometry and applied to the enrichment of phosphopeptides. The method has remarkably specific enrichment capacity for phosphopeptides from complex biological samples.

研究领域: 分析化学 · 生物化学 · 蛋白质组学
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POLYMER INTERNATIONAL · 2021 ·Vol. 70 ·期 9 ·1376-1385 · IF 2.99

Synthesis of cucurbit[6]uril pendent upper critical solution temperature type copolymers: self-assembly and multi-stimuli-responsive behavior

Yanli Li,YeFang Yang,Xinqi Pei,Yu Li,Yuhui Yuan,Xiaoling Huang

Cucurbit[6]uril-derivatized vinyl monomer (cucurbit[6]uril methacrylate) was synthesized. Acrylic acid (AA) was used as the comonomer for copolymerization with the cucurbit[6]uril-derivatized monomer. A series of copolymers of poly(acrylic acid- co -cucurbit[6]uril methacrylate) (PAA- co -CB[6]MA) were synthesized by free radical polymerization. The cucurbit[6]uril-derivatized monomer and PAA- co -CB[6]MA copolymers were characterized by 1 H NMR spectra, high-resolution mass spectroscopy and gel permeation chromatography. The solution behavior was examined using UV–visible spectroscopy and dynamic light scattering. The PAA- co -CB[6]MA showed an upper critical solution temperature (UCST) in water. The UCST-type thermoresponsive behavior of these CB[6]-derivatized copolymers was highly dependent on the composition of the copolymer. For the same type of copolymer, changes in its composition gave rise to different UCSTs. Additionally, the PAA- co -CB[6]MA copolymers were successful in trapping azocarmine B. The stimuli-responsive release of encapsulated azocarmine B was achieved by a combination of temperature and pH value stimuli. According to the results, the novel PAA- co -CB[6]MA copolymers can be used as carriers. © 2021 Society of Industrial Chemistry.

CAS / MDL: 2638-94-0 920-46-7
研究领域: 高分子化学 · 材料科学
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TALANTA · 2025 · IF 6.1

Cucurbit[6]uril host-guest interaction assisted N-terminal epitope imprinted particles for cytochrome c recognition prepared by reversible addition-fragmentation chain transfer strategy

Nurimangul Muntiza,Wenbin Zhang,Yuzeng Li,Wenquan Ji,Jin Zhao,Hongfeng Zhang,Qinran Li,Qiliang Deng,Donglan Sun,Tianjun Liu

A novel strategy for cytochrome c selective recognition assisted with cucurbit[6]uril by host-guest interaction via N-terminal epitope imprinting and reversible addition-fragmentation chain transfer (RAFT) polymerization was developed. N-terminal nonapeptide of cytochrome c (GI-9) was used as the epitope template to achieve highly selective recognition of cytochrome c . As a common supramolecule in recent years, cucurbit[6]uril can encapsulate the butyrammonium group of lysine residue to capture the peptide and improve the corresponding spatial orientation by the host-guest interaction for GI-9 or cytochrome c recognition. After cucurbit[6]uril modification and epitope immobilization, the imprinted polymer was synthesized by RAFT polymerization with 2-dodecylsulfanylcarbothioylsulfanyl-2-methylpropanoic acid as chain transfer agent. After template removal, the obtained imprinted particles showed good binding ability to GI-9 (20.28 mg g −1 , IF = 4.11) and cytochrome c (36.12 mg g −1 , IF = 3.91). With the successive addition of cucurbit[6]uril and RAFT agent, the step-by-step improvement of the IF for cytochrome c recognition further illustrated the effects of supramolecular host-guest interaction and regulation of imprinted polymer chain. The imprinted polymers showed obvious advantages for cytochrome c recognition compared to competitive proteins and had good reusability with the repeated reproduction rate 80.8 % after five cycles of adsorption and desorption. Furthermore, the selective recognition for cytochrome c in adult bovine serum proved its potentiality to be applied in practical samples. All these results demonstrated that the combination of epitope imprinting, cucurbit[6]uril host-guest interaction and RAFT strategy presented an efficient new feasible control method for protein recognition with good selectivity, stability and reusability.

研究领域: 生物化学 · 分子生物学 · 材料科学
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MICROCHIMICA ACTA · 2019 ·Vol. 186 ·期 12 ·1-10 · IF 5.479

Monohydroxycucurbit[7]uril-coated stir-bar sorptive extraction coupled with high-performance liquid chromatography for the determination of apolar and polar organic compounds

Dong Nan,Zhang Lingxue,Yao Jianmei,Ma Peijian,He Jing,Li Tao,Wang Yuan

A detailed study has been carried out on monohydroxycucurbit[7]uril-based stir-bar sorptive extraction (SBSE). A polydimethylsiloxane coating was produced by a sol–gel technique and doped with monohydroxycucurbit[7]uril ((HO) 1 Q [7]) as a selective sorbent phase. (HO) 1 Q [7] was chemically bound to the sol–gel silica substrate through hydrolysis and polycondensation. The coating possesses a porous surface, shows strong solvent resistance and good thermal stability, and has a long lifespan. Four groups of compounds, with polarities ranging from apolar polycyclic aromatic hydrocarbons to polar ketones, aromatic amines and phenols, were selected as test analytes. They were extracted with the coated stir bar, then desorbed with methanol and quantified by high-performance liquid chromatography with ultraviolet detection. The limits of detection range between 1.3 and 15 μg L −1 , the linear ranges extend from 5 to 10,000 μg L −1 , and the relative recoveries from spiked samples range between 76.4 and 97.9%. The intraday relative standard deviations range from 2.3 to 8.6% (for n  = 3, at 500 μg L −1 ). Compared with a commercial PDMS-coated stir bar and a polyether sulfone-coated stir bar, the new stir bar shows wider applicability and better extraction efficiency for each group of compounds. In addition, the stir bar can simultaneously extract mixtures of chemicals of different polarities. This endows it with the potential for recovering a broad group of polar organic compounds. A stir bar for sorptive extraction based on monohydroxycucurbit[7]uril has been prepared by a sol–gel technique. The stir bar coupled with HPLC with UV detection allows for the determination of a variety of polar compounds and multicomponent mixtures, respectively.

研究领域: 分析化学 · 环境科学
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Polymer Chemistry · 2013 ·Vol. 4 ·期 15 ·4192-4198 · IF 5.231

Supramolecular ternary polymer mediated by cucurbituril and cyclodextrin

Qian Wang,Yong Chen,Yu Liu

A novel supramolecular ternary polymer mediated by macrocyclic molecules cucurbit[8]uril (CB[8]) and cyclodextrin was successfully constructed, based on the CB[8]-stabilized charge-transfer (CT) interaction and cyclodextrin–adamantane host–guest interaction. Herein, we synthesized a naphthol-modified β-cyclodextrin (Np-β-CD) and an adamantane–viologen ditopic guest to obtain a ditopic host–guest complex with a preorientational donor–acceptor pair. Furthermore, after addition of CB[8] to the complex, the donor–acceptor pair of naphthol–viologen was encapsulated into the cavity of CB[8] leading to a linear supramolecular polymer which was well characterized by various methods, including DOSY, DLS, SEM, TEM and AFM. This work enriches the field of supramolecular polymers and provides a novel method to fabricate supramolecular architectures with multiple macrocyclic host molecules.

CAS / MDL: 2094-72-6 34626-51-2
研究领域: 超分子化学 · 材料科学
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