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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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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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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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POLYHEDRON · 2022 · IF 2.975

Supramolecular self-assembly between symmetric tetramethyl cucurbit[6]uril and dimethylphenylpiperazine hydrochloride

Jian-Hang Hu,Zhi-Chao Yu,Jia-Yi Zhang,Zhi-Nian Liu,Run-Xin Hou,Yu Xiong,Carl Redshaw,Zhu Tao,Xin Xiao

The interaction between symmetric tetramethyl cucurbit[6]uril (TMeQ[6]) and 2,3-dimethylphenylpiperazine hydrochloride (PMY) has been studied in the presence of [CdCl 4 ] 2− . Each port of the TMeQ[6] is connected to PMY through weak interactions such as ion dipole interactions and C H⋯O hydrogen bonding interactions, whilst the [CdCl 4 ] 2− is connected with the portal carbonyl oxygen, glycoside urea methylene and a bridging methylene of a TMeQ[6] molecule via ion–dipole interactions. These interactions were evident from a single crystal X-ray diffraction study of TMeQ[6]-PMY-[CdCl 4 ] 2− . In addition, the complex can form a one-dimensional supramolecular chain structure, and then assemble into a two-dimensional supramolecular framework, which can be described as a TMeQ[6]-PMY-[CdCl 4 ] 2− based supramolecular framework (QSF).

研究领域: 化学 · 材料科学
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RSC Advances · 2021 ·Vol. 11 ·期 6 ·3470-3475 · IF 3.361

Host–guest modes and supramolecular frameworks of complexes of tetramethyl cucurbit[6]uril with 4-chloroaniline and 4,4′-diaminostilbene

Ye Meng,Weiwei Zhao,Jun Zheng,Daofa Jiang,Jie Gao,Yanmei Jin,Peihua Ma

Since the first reportal on decamethylcucurbit[5]uril (Me10Q[5]) in 1992, substituted cucurbit[n]urils have attracted considerable research interest. In this study, the host–guest modes between the tetramethyl cucurbit[6]uril (TMeQ[6]) as a host and 4-chloroaniline and 4,4′-diaminostilbene (G1 and G2) as guests were investigated by single-crystal X-ray diffraction, NMR, ITC, UV-Vis spectrum, and MALDI-TOF mass spectrometry analyses. The experimental results showed that TMeQ[6] formed a 1 : 1 inclusion compound with G1, and the carbonyl portal of TMeQ[6] formed a 1 : 1 self-assembly with G2. Further, multi-dimensional supramolecular frameworks were formed driven by weak interaction forces in the system (hydrogen bonding, C–H⋯π interactions, ion–dipole interactions, and dipole–dipole interactions).

研究领域: 化学 · 超分子化学 · 结构化学
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Journal of Chemistry · 2020 ·Vol. 2020 ·期 1 ·9619461 · IF 1.79

Synthesis, Adsorption, and Recognition Properties of a Solid Symmetric Tetramethylcucurbit[6]uril-Based Porous Supramolecular Framework

Fei-Yang Tian,Rui-Xue Cheng,Yun-Qian Zhang,Zhu Tao,Qian-Jiang Zhu

In this work, we reported a porous supramolecular framework ( A ) constructed of a symmetric tetramethylcucurbit[6]uril (TMeQ[6]) in aqueous HCl solutions; the driving force was the outer surface interaction of cucurbit[ n ]urils, as well as hydrogen bonding between latticed water molecules and portal carbonyl oxygens of TMeQ[6]. Adsorption experimental results revealed that the porous supramolecular framework can absorb certain fluorophore guests ( FG s) to form luminescent assemblies ( FG @ A s) by fluorescence enhancement or colour change, and some of them can respond to certain volatile organic compounds. Thus, the TMeQ[6]-based supramolecular framework could be used as a sensor for certain gas or volatile compounds.

研究领域: 化学 · 材料科学 · 分析化学
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