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JOURNAL OF CHROMATOGRAPHY A · 2014 · IF 4.258

Preparation and chromatographic performance evaluation of cucurbit[7]uril immobilized silica

Liyun Ma,Si-Min Liu,Lin Yao,Li Xu

Cucurbit[7]uril (CB7), one host macromolecule, possesses a hydrophobic inner cavity and two identical hydrophilic carbonyl fringe portals, thus interacting with a variety of guest molecules through hydrophobic, hydrogen bonding and ion–dipole interactions. These characteristics make CB7 a good candidate as the stationary phase (SP) modifier in high performance liquid chromatography (HPLC). In the present work, CB7 was immobilized onto silica (CB7-SiO 2 ) by a sol–gel approach. The obtained CB7-SiO 2 was characterized by Fourier transform infrared spectroscopy, thermogravimetric analysis and elemental analysis. The chromatographic performance of CB7-SiO 2 was then studied in detail, in both reversed phase (RP) and hydrophilic interaction liquid chromatographic (HILIC) modes. For probe aromatic compounds and dyes, the typical RP behavior was observed, mainly due to the predominant hydrophobic interaction between the analytes and CB7-SiO 2 . For probe alkaloids, the “U-shape” curves were obtained; in the methanol-rich part, HILIC performance was obvious, probably owing to hydrogen bonding and ion–dipole interactions. Compared to bare SiO 2 SP, the stronger retention and different selectivity were observed on CB7-SiO 2 . The CB7-SiO 2 SP remained stable within at least 11,000 column volumes of the MP, revealing the satisfactory stability of it. The proposed method integrated the advantages of CB7 and sol–gel method provided a feasible way for the wider application of CBs in separation science.

研究领域: 分析化学 · 分离科学
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MICROCHEMICAL JOURNAL · 2024 · IF 4.9

Cucurbit[7]uril-mediated matrix solid phase dispersion extraction strategy combined capillary electrophoresis for detection of biogenic amines in foods

Huiyu He,Rongbin Nie,Nan Dong

Biogenic amines (BAs) are the vital indicators of food freshness, and monitoring the change of BAs content is quite essential for food safety. Herein, we developed a matrix solid phase dispersion (MSPD) extraction technology based on cucurbit[7]uril (Q[7]) to extract BAs from pork and shrimp. Then, the extracted BAs were analyzed by capillary electrophoresis (CE) with low sample consumption and high analytical efficiency. The factors affecting MSPD extraction were optimized by Plackett-Burman and the Box-Behnken design (BBD). The limits of detection (LODs) were ranging from 0.003 to 0.019 mg kg −1 , the recoveries of spiked samples were 80.15 %–110.3 %. The satisfactory accuracy and precision were attributed to the host–guest interaction between Q[7] and BAs. Furthermore, the freshness of pork and shrimp was evaluated by simultaneous determination of four BAs. For its wide linear range, high sensitivity, and cost-effectiveness, the proposed Q[7] mediated MSPD-CE-UV provides meaningful potential prospects in the rapid monitor of food freshness and safety.

CAS / MDL: 107-22-2 57-13-6
研究领域: 食品安全 · 分析化学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2025 · IF 4.6

Development of an extractive spectrophotometric method for the determination of spermidine in urine samples using cucurbit[7]uril-truxene derivative as a fluorescent extractant

Xiaojing Yang,Tingyi Qiao,Fengping Hou,Nan Dong

Spermidine has emerged as a promising biomarker for the early-stage diagnosis of cancer in humans. A novel extractive spectrophotometric analytical method has been developed for the determination of spermidine in urine samples. This technique leverages the selective extraction of spermidine from complex matrices using a cucurbit[7]uril-truxene derivative (Q[7]-Cs-Tr) as a fluorescent extractant. The Q[7]-Cs-Tr forms a stable host-guest complex with spermidine, facilitating its extraction from the aqueous phase to the organic phase. The formation of this complex results in a decrease in the fluorescence intensity of the Q[7]-Cs-Tr in the organic phase. Key factors influencing extraction efficiency, including the type of dispersed organic solvent, extractant concentration, solution pH, extraction times, and equilibrium time, were thoroughly investigated. The method demonstrated minimal interference from various metal ions, anions, amino acids, and other biogenic amines. It also exhibited a low limit of detection (8.6 nM), excellent linearity (R 2  = 0.9972), and high repeatability (RSD = 2.4 % intra-day, RSD = 3.6 % inter-day). The proposed method was successfully applied to determine spermidine levels in urine samples, yielding satisfactory recoveries ranging from 96.3 % to 103.5 %. Compared to existing methods, this approach is simple, reliable, highly sensitive, and exhibits low interference, making it a potential robust tool for clinical diagnostics.

研究领域: 分析化学 · 生物化学 · 临床诊断学
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ACS Applied Optical Materials · 2023 · IF 0

Supramolecular Inclusion Complexes Based on Cucurbit[7]uril and Triazine-Bridged Viologens Displaying Near-Infrared Photochromism and Photomodulable Fluorescence

Long-Jing Wu,Rui Fu,Guozheng Huang,Rui-Lian Lin,Jing-Xin Liu

The design and construction of near-infrared (NIR) photochromic materials that show absorption and responsiveness in the NIR region remain a challenge. In this work, we prepared two triazine-bridged viologens, one being 2,4,6-tri(4-pyridinium)-1,3,5-triazine trichloride (TPA·Cl3) and the other one being its tribenzyl-substituted derivative (TPB·Br3). 1H NMR spectroscopy reveals that the cucurbit[7]uril (Q[7]) can bind with the two viologens to form quaternary inclusion complexes TPA3+@Q[7]3 and TPB3+@Q[7]3. Both inclusion complexes demonstrate NIR photochromic behavior, and the color changed from white to bluish green. Electron-spin resonance (ESR) spectra indicate that their photochromism is due to the formation of free radicals TPA•2+/TPB•2+. In addition, the inclusion complexes show photomodulable fluorescence emission. The excellent photochromic behavior and photomodulable fluorescence endow the inclusion complexes with practical utility in erasable inkless printing and anticounterfeiting.

研究领域: 化学 · 材料科学 · 物理化学
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JOURNAL OF APPLIED POLYMER SCIENCE · 2025 · IF 2.8

Direct Cross-Linking of Cucurbit[7]uril Pseudopolyrotaxanes to Prepare Slide-Ring Hydrogels

Lei Zou,Jiajun Ren,Fangdong Ning,Xianmei Ma,Matthew J. Webber,Yongjun Zhang

Slide-ring hydrogels have been shown to have exceptional toughness and stretchability. Current designs typically rely on polyrotaxane architectures of cyclodextrin (CD) macrocycles treaded onto polyethylene glycol (PEG) chains. The use of alternative macrocycles to prepare slide-ring hydrogels remains largely unexplored. In this study, we present a cucurbit[7]uril (CB[7]) slide-ring hydrogel prepared from multiblock PEG polymers segmented with guest moieties of varying affinity for binding to CB[7]. Following threading with allyl-modified CB[7] to form pseudopolyrotaxane structures, the side-chains are then covalently cross-linked to yield the slide-ring architecture. The resulting hydrogels exhibit unique mechanical properties modulated by host–guest binding affinity and dynamics. Given the exceptional molecular recognition capabilities of the CB[n] family of macrocycles for diverse guests, using these as alternatives to CDs offers an opportunity to expand the design space for slide-ring hydrogel architectures.

研究领域: 材料科学 · 高分子化学 · 超分子化学 · 材料力学性能
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2024 · IF 4.9

Organic room-temperature phosphorescence of imidazole-based films by self-assembly enhancement strategies

Hui Li,Qian Zhang,Hean Zhang,Qianling Cui,Chuanming Liu,Lidong Li

Organic room-temperature phosphorescence (RTP) shows high potential in optical fields, and self-assembly method via various non-covalent interactions is one facile and efficient way to enhance RTP performance. Herein, we investigated the RTP behaviors of three imidazole-based polymer films containing imidazole, methyl imidazolium, and benzyl imidazolium moieties, respectively. Their RTP behaviors and chemical structures were compared and discussed to explore the underlying structure-properties relationships. Owing to plenty of hydrogen bonds of polyacrylamide matrix to lock phosphors, imidazolium-based films gave an obvious green RTP due to cations and iodine anions-enhanced intersystem crossing. The blue RTP signals of imidazole-containing film was aroused by coordination with Zn 2+ ions due to crosslinking and heavy atom effects. Moreover, the RTP performance of benzyl imidazolium-based film was remarkably improved by host-guest complexation with cucurbit[7]uril, showing a long lifetime up to 230.6 ms. By utilizing the difference in their RTP lifetimes, information encryption application was successfully achieved as a proof of concept.

CAS / MDL: 79-06-1
研究领域: 光学材料 · 材料科学 · 物理化学
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NEW JOURNAL OF CHEMISTRY · 2018 ·Vol. 43 ·期 1 ·407-412 · IF 3.201

Supramolecular self-assemblies of inverted cucurbit[7]uril with biogenic amines

Pei-Hui Shan,Zhi-Rui Zhang,Dong Bai,Bing Bian,Zhu Tao,Xin Xiao

The interactions between inverted cucurbit[7]uril (iQ[7]) and six biogenic amines, namely tyramine (TA), 2-phenylethylamine (PEA), histamine (HI), tryptamine (TR), spermine (SPM), and spermidine (SPD), were studied through 1H nuclear magnetic resonance (NMR) spectroscopy, UV/vis absorption spectroscopy, fluorescence spectroscopy, isothermal titration calorimetry (ITC), and matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS). The results showed that iQ[7] exhibits binding affinity towards five of these biogenic amines, with the exception of HI, and that the host–guest binding sites differ depending on the structure of the biogenic amine. For the aromatic amines (TA and PEA), the phenyl groups are completely encapsulated within iQ[7]; for the heterocyclic aromatic amine TR, there is deep inclusion of its indole group in the cavity of iQ[7]; for the fatty amines (SPM and SPD), the central alkyl chain is bound within the central cavity of iQ[7].

研究领域: 化学 · 生物学 · 医学
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ANALYTICAL AND BIOANALYTICAL CHEMISTRY · 2025 · IF 3.8

Self-assembled aggregation-induced emission supramolecular probe for sensitive temozolomide detection and intracellular imaging

Jiang Chenrui,Chen Feifei,Chen Yue,Sun Yu,He Hua,Dramou Pierre,Xu Tao,Xu Hongbin

Temozolomide (TMZ) is a first-line chemotherapy drug for treating malignant glioblastoma but faces challenges due to its short plasma half-life and limited brain distribution. There is a need for a more efficient, cost-effective, and sensitive method for monitoring TMZ in clinical settings. This work presents a novel fluorescent probe based on the host–guest interaction of cucurbit[7]uril (CB[7]) and aggregation-induced emission molecule 1,1,2,2-tetra(biphenyl-4-yl)ethene (TTPE) for trace-level detection of TMZ in serum. The CB[7]@TTPE nanoprobe demonstrated high sensitivity, with a detection range of 1–20 μg/mL and a limit of detection of 0.25 μg/mL. Comprehensive characterization by ITC, FT-IR, NMR, UV–vis, and fluorescence spectroscopy confirmed the sensing behavior of the probe. The system exhibited excellent selectivity for TMZ and was successfully applied to serum samples with good recovery rates. In addition, the probe enabled fluorescence imaging of TMZ in human glioma cells (U87 and T98G), making it suitable for monitoring of drug distribution in cellular environments. The self-assembled CB[7]@TTPE probe provides a highly sensitive and selective method for TMZ detection in biological fluids. Its strong fluorescence and water solubility offer promising potential for both clinical diagnostics and drug resistance monitoring in cancer therapy. Graphical

CAS / MDL: 85622-93-1
研究领域: 分析化学 · 生物化学 · 超分子化学 · 药学 · 生物医学工程 · 肿瘤学
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Aggregate · 2025 · IF 13.7

Cucurbit[7]Uril-Based Supramolecular Polymers With Dual Photochromism and Fluorescence: From Host‒Guest Design to Smart Applications

Long-Jing Wu,Anqi Deng,Jing-Xin Liu,Rui-Lian Lin,Ming-Fu Ye,Guo-Zheng Huang

The development and fabrication of cucurbit[7]uril (Q[7])-based host‒guest supramolecular polymers remain challenging due to the limited cavity size of Q[7]. Herein, we designed and synthesized three thiophene-pyridinium guests and investigated their binding interactions with Q[7]. NMR, ESI-MS spectroscopy, and DFT calculations revealed that Q[7] can encapsulate one or two thiophene groups of the guests to form supramolecular complexes, including discrete inclusion complexes and supramolecular polymers. Importantly, all supramolecular complexes demonstrated reversible photochromism in the solid state, which is attributed to viologen radical generation, as confirmed by UV-vis-NIR, ESR, and DFT studies. Due to the aggregation caused quenching (ACQ) effect induced by the intermolecular π⋯π stacking interaction of thiophene groups within the Q[7] cavity, the Q[7]-based supramolecular polymers remained fluorescence-silent, whereas the discrete inclusion complexes showed enhanced fluorescence compared to their thiophene-pyridinium guests. The dual photochromic and fluorescence properties of the Q[7]-based supramolecular complexes render them suitable for applications in erasable inkless printing, multi-level anti-counterfeiting, and advanced information encryption. This study provides a strategy for constructing dual-functional supramolecular polymers using Q[7]-based host‒guest interactions.

研究领域: 超分子化学 · 材料科学 · 光化学 · 高分子科学 · 应用化学
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JOURNAL OF NANOBIOTECHNOLOGY · 2025 · IF 12.6

Enzyme-assisted nanopore sensor for sensitive and multiplexed detection of microRNAs

Huang Xiaobin,Yi Yakun,Zhou Ke,Liu Lei,Wu Hai-Chen

MicroRNAs (miRNAs) play crucial roles in the pathogenesis of diverse diseases; however, their extremely low abundance in complex biological systems makes highly sensitive and specific multiplexed detection particularly challenging. Here, we report an enzyme-assisted nanopore sensor that enables simultaneous and ultrasensitive detection of multiple miRNAs. Capture DNA (cDNA) immobilized on streptavidin-coated magnetic beads specifically hybridizes with target miRNAs, opening the cDNA hairpin and facilitating the binding of alkaline phosphatase (ALP)-labeled detection DNA to form stable complexes. ALP catalyzes the dephosphorylation of designed phosphorylated peptide probes, inducing conformational and charge changes that yield distinct current blockade signatures in the presence of cucurbit [ 7 ]uril within the nanopore. This strategy reduces background interference via magnetic separation and amplifies detection signals through enzymatic reactions, thereby markedly improving sensitivity for low-abundance miRNAs. The sensor achieves a broad dynamic range from 10.0 fM to 10.0 nM across three target miRNAs, with femtomolar-level limits of detection. By integrating molecular separation, enzymatic amplification, and nanopore sensing, this platform provides a robust approach for precise miRNA analysis, offering strong potential for early disease diagnosis.

CAS / MDL: 60-00-4
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Theranostics · 2019 · IF 8.063

Supramolecular therapeutics to treat the side effects induced by a depolarizing neuromuscular blocking agent

Xiangjun Zhang,Qian Cheng,Lanlan Li,Liqing Shangguan,Chenwen Li,Shengke Li,Feihe Huang,Jianxiang Zhang,Ruibing Wang

Succinylcholine (Sch) is the only depolarizing neuromuscular blocking agent widely used for rapid sequence induction in emergency rooms. Unfortunately, a variety of (sometimes lethal) adverse effects, such as hyperkalemia and cardiac arrest, are associated with its use, and currently there are no specific antidotes to reverse Sch or to treat these side-effects. Methods: The binding behaviors of Sch and several synthetic receptors, including cucurbit[7]uril, sulfo-calix[4]arene and water-soluble carboxylatopillar[6]arene (WP[6]), were first investigated. With a mouse model, a leathal dose of Sch was selected for evaluation of the antidotal effects of these synthetic receptors on Sch induced mortality. The antidotal effects of a selected synthetic receptor, WP[6], on Sch induced cardiac arrhythmias, hyperkalemia, rhabdomyolysis and paralysis were subsequently evaluated with rat and mouse models. The reversal mechanism was also investigated at a cellular level. Results: All of these macrocyclic molecules exhibited relatively high binding affinities with Sch in vitro . In a Sch-overdosed mouse model, immediate injection of these synthetic receptors right after Sch administration increased the overall survival rate, with WP[6] standing out with the most effective antidotal effects. In addition, administration of WP[6] also reversed the paralysis induced by Sch in a mouse model. Moreover, infusion of WP[6] to Sch-overdosed rats reduced the incidence of cardiac arrhythmia, inhibited the otherwise abnormally high serum potassium levels, and relieved the muscular damage. At the cellular level, WP[6] reversed the Sch induced depolarization and reduced the efflux of intracellular potassium. Conclusion: Synthetic receptors, particularly WP[6], exhibited high binding affinities towards Sch, and presented a significant potential as supramolecular therapeutics to treat the various side effects of Sch by specifically sequestering Sch in vivo .

研究领域: 药理学 · 药物化学 · 治疗学
✓ 已验证 DOI PubMed 高影响因子
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INTERNATIONAL JOURNAL OF PHARMACEUTICS · 2024 · IF 5.3

Cucurbit[7]uril-based host–guest complexes for improving bioavailability and reducing side effects of piroxicam

Yan Wang,Xiaodi Yang,Jianguo Luo,Sisi Yi,Tao Guo,Yue Liao,Chao Yu,Xiangjun Zhang

Piroxicam (PX) is a nonsteroidal anti-inflammatory drug (NSAID) commonly associated with gastrointestinal (GI) injuries, including dyspepsia, heartburn, inflammation, bleeding, ulceration, and life-threatening perforation. The β-cyclodextrin (β-CD)-based PX formulation (PX@CD) has been shown to reduce gastric side effects by improving PX’s solubility and dissolution rates. However, the solubility of PX can only be increased to a limited extent by β-CD, due to the low binding constant between PX and β-CD (∼100 M −1 ). As a result, adverse reactions such as epigastric pain and pyrosis are still commonly reported. Cucurbit[7]uril (CB[7]) is a synthetic macrocyclic host compound that binds strongly to various drugs. In this study, we demonstrated that CB[7] forms complexes with PX in the gastric acid environment with a binding constant approximately 70 times higher than that between β-CD and PX. The PX@CB[7] inclusion complexes exhibited rapid dissolution rates in the gastric environment. In addition, PX@CB[7] showed significantly higher oral bioavailability and maximum concentration (C max ) compared to PX and PX@CD (1:2.5), resulting in improved anti-inflammatory effects in both mouse and rat models. Moreover, PX@CB[7] (1:2.5) had the least adhesion to the gastric mucosa and caused the mildest gastric side effects in rat models when compared to PX, PX@CD (1:2.5), and PX@CB[7] (1:1). Lastly, CB[7] demonstrated good oral biocompatibility in a subacute toxicity evaluation study. These findings indicate that CB[7] could be used as an excipient to improve treatment effectiveness and decrease adverse reactions in orally administered formulations with a favorable safety profile.

CAS / MDL: 96684-39-8
研究领域: 药学 · 药物递送系统 · 药理学 · 毒理学
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