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cucurbit[8]uril
DYES AND PIGMENTS · 2022 · IF 5.122

A cucurbit[8]uril-based probe for the detection of the pesticide tricyclazole

Heng Wu,Jie Zhao,Xi Nan Yang,Dan Yang,Li Xia Chen,Carl Redshaw,Li Guo Yang,Zhu Tao,Xin Xiao

A system comprising cucurbit[8]uril (Q[8]) and a fluorescent molecule (E)-1-(2-hydroxyethyl)-4-(4-hydroxystyryl)pyridin-1-ium bromide (HPy) has been utilized to construct a fluorescent probe that is capable of detecting the pesticide tricyclazole (TC). A variety of techniques including 1 H NMR spectroscopy together with fluorescence experiments have been employed to investigate the host-guest properties of the Q[8]/HPy system in aqueous solution. Results indicate that the system forms the stable2:1 inclusion complex HPy 2 @Q[8], and that this inclusion complex imparts fluorescent quenching on HPy. The addition of a number of pesticides was found to have no obvious effect on the fluorescence, however on addition of tricycazole (TC), the fluorescence intensity underwent a dramatic enhancement. The linear relationship between the fluorescence intensity and the concentration of TC allowed for the facile detection of TC concentration in aqueous target solutions as well as in agricultural products. The detection limit was found to be 3.70 × 10 −8  mol L −1 .

研究领域: 分析化学 · 环境科学
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Journal of Materials Chemistry A · 2024 · IF 10.7

Cucurbit[8]uril as a Supermolecular Lock for Designing Dual-chain Conjugated Polymer for Enhanced H2O2 Production Photocatalyst.

Jie Yin,Sizhe Li,Hao Zhang,Yao Lu,Yan Zhao,Kai A. I. Zhang

Conjugated polymers (CPs) have garnered attention for their tailorable structure properties, particularly in the context of efficient photosynthetic hydrogen peroxide (H2O2) production. However, the challenge lies in the precise molecular engineering of CPs to facilitate differing reaction pathways, thereby enhancing H2O2 photogeneration efficiency. In this study, we developed dual-chain CPs (DC-CPs) with a distinctive architecture, employing the supramolecular host cucurbit[8]uril as a "molecular lock" to conjoin two polymer chains. The dual-chain configuration is designed to harbour a central reaction centre conducive to oxygen reduction, providing dual conduction pathways for reactant molecules. The existence of this central reaction center was confirmed through the in-situ diffuse reflectance infrared Fourier transform (DRIFT) spectroscopy measurements and density functional theory (DFT) calculations. In addition, femtosecond transient absorption (fs-TAS), variable temperature fluorescence spectroscopy and time-resolved photoluminescence (TRPL) measurements reveal double-stranded structures favourable for carrier transport and reactive site activation between dual polymer chains. Ultimately, DC-CPs demonstrate up to a threefold increase in H₂O₂ production compared to their respective single-chain CPs (SC-CPs). This work adds significantly to the application of CPs for efficient H2O2 photogeneration through molecular engineering strategy.

CAS / MDL: 30525-89-4
研究领域: 材料科学 · 光催化 · 超分子化学
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JOURNAL OF MOLECULAR STRUCTURE · 2026 · IF 4.9

Cucurbit[8]uril-based supramolecular self-assembly for nitrophenol adsorption

Jinlong Yao,Shangwei Yuan,Li Zeng,Jihong Lu,Baoqiu Yu,Zhichao Yu,Xin Xiao

Three nitrophenol@Q[8] host-guest single crystals are obtained and fully resolved for the first time. • A laboratory-scale recyclable Q[8] adsorption-ethanol desorption procedure is developed for mixed nitrophenol removal. • Q[8]@Nitrophenol host-guest recognition is cross-validated by multiple techniques. Cucurbit[8]uril (Q[8]) was employed as an adsorbent to systematically investigate its adsorption performance, interaction mechanism, and recycling potential toward o-nitrophenol (2-NP), m-nitrophenol (3-NP), and p-nitrophenol (4-NP) in aqueous solutions. Single-crystal X-ray diffraction analysis of the Q[8]-nitrophenol assemblies revealed that π-π stacking and hydrogen-bonding interactions governed the crystalline framework. Furthermore, a cyclic adsorption–desorption process was developed, leveraging the reversible nature of the host–guest interactions, which allowed for the effective regeneration and reuse of Q[8]. After treatment with Q[8], the residual concentrations of all three nitrophenol isomers in the aqueous phase fell below the first-level discharge limit of 2.0 mg·L⁻¹.

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ACS Sensors · 2025 · IF 9.1

Machine Learning-Assisted Chemical Tongues Based on Dual-channel Inclusion Complexes for Rapid Identification of Nonsteroidal Anti-inflammatory Drugs in Food

Lian Xu,Yan Xiao,Kun Yu,Hongshuo Pan,Jiayi Xu,Yiyun Guan,Mengke Wang,Xiangyu Xu,Hao Wang

The improper application of nonsteroidal anti-inflammatory drugs (NSAIDs) presents significant health hazards via vector food contamination. A critical limitation of these traditional existing approaches is their inability to concurrently discern and distinguish among diverse NSAIDs, presenting a notable gap in the analytical capabilities within this domain. Herein, a creative dual-channel fluorescence sensor array was developed for the rapid discrimination and determination of NSAIDs, utilizing complexes of cucurbit[8]uril (CB[8]) with three distinct modified poly(ethylenimines) (PEIs) to address this challenge. The array successfully differentiated and identified 19 NSAIDs with 97% accuracy at a concentration of 1 mM. In addition, it also achieved analyses of individual NSAIDs across a range of concentrations, NSAID mixtures, and impurities of aspirin using statistical analysis methods. More importantly, the approach effectively detected NSAIDs in complex matrices, such as milk and urine, demonstrating its potential for real-world applications.

研究领域: 分析化学 · 食品安全 · 药物检测
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JOURNAL OF MOLECULAR STRUCTURE · 2026 · IF 4.7

Cucurbit[8]uril-mediated efficient separation of o-nitrotoluene from nitrotoluene isomers

Xutao Ding,Li Zeng,Peijian Ma,Rui Wang,Jinlong Yao,Zhichao Yu,Yu Xia,Xin Xiao

Nitrotoluene isomers are vital chemical intermediates, but their separation is challenging due to similar properties. This work introduces a supramolecular strategy using cucurbit[8]uril (Q[8]) to selectively isolate ortho-nitrotoluene (ONT). Through methods including single-crystal XRD, ITC, GC, and theoretical calculations, host–guest interactions in formic acid were characterized. Gradient solvent volatilization of Q[8] with isomer mixtures enabled controlled crystallization. Results show Q[8] strongly prefers ONT, with binding constants of 3.628×10⁶ M⁻¹ (ortho) vs. 8.712×10⁵ M⁻¹ (meta) and 2.173×10⁵ M⁻¹ (para), giving selectivity ratios of 4.16 and 13.37, respectively. Crystal structures reveal stabilization via π–π stacking and hydrogen-bonding networks. These interactions drive multidimensional assembly into ordered architectures through synergistic surface interactions, hydrogen bonding, and aromatic stacking. This work extends cucurbituril applications in adsorption and separation.

CAS / MDL: 88-72-2 99-99-0 99-08-1
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LANGMUIR · 2013 · IF 4.187

Cucurbit[8]uril Supramolecular Assembly for Positively Charged Ultrathin Films as Nanocontainers

Dan-dan Li,Ke-feng Ren,Hao Chang,Hai-bo Wang,Jin-lei Wang,Chao-jian Chen,Jian Ji

The design of positively charged ultrathin films for surface modification is of crucial importance for biomedical applications. Herein, we report the layer-by-layer assembly of pure positively charged ultrathin films based on the host–guest interaction of cucurbit[8]uril (CB[8]). Two positively charged poly(ethylenimine)s (PEI) functionalized with guest moieties methyl viologen (MV) and indole (ID) were alternately assembled with the formation of CB[8] ternary complex under basic conditions. The growth of the (PEI-MV@CB[8]/PEI-ID) films was monitored by spectroscopic ellipsometry and quartz crystal microbalance. The morphology and structure of the films were characterized by scanning electron microscopy and UV–vis spectroscopy, respectively. These positively charged (PEI-MV@CB[8]/PEI-ID) films were very stable in the pH range from 4 to 9 but disassembled immediately when subjected to a competitive guest adamantylamine. Finally, the films were successfully employed as nanocontainers for DNA loading and subsequent directing the transfection of the adhered cells.

CAS / MDL: 553-26-4 830-96-6
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CHEMICAL RESEARCH IN CHINESE UNIVERSITIES · 2023 ·Vol. 39 ·期 6 ·1058-1063 · IF 3.1

Supramolecular Self-assembly Formed from Cucurbit[8]uril and p-Hydroxybenzoic Acid

Wang Chenghui,Yu Zhichao,Bai Qinghong,Pan Dingwu,Prior Timothy J.,Tao Zhu,Redshaw Carl,Xiao Xin

T he binding behavior of cucurbit[8]uril(Q[8]) and p -hydroxybenzoic acid(p-HBA) has been investigated using 1 H NMR titration experiments, UV-Vis absorption, isothermal titration calorimetry(ITC), and X-ray crystallography. Results revealed that the Q[8] can accommodate two p -HBA molecules to form a 1:2 host-guest inclusion complex in solution, namely ( p -HBA) 2 @Q[8]. From a poorly scattering crystal, we were able to identify two symmetry unique Q[8] rings, but with different p -HBA fillings. The structure can be represented as Q[8]+1.5 p -HBA, which gives Q[8]@(p-HBA) 2 ·Q[8]@ p -HBA as the structural formula. This supramolecular structure was screened for its ability to capture iodine. The experimental results showed that the adsorption efficiency of the supramolecular organic framework material for iodine capture was 43.8%, with an equilibrium adsorption capacity of 223.3 mg/g.

CAS / MDL: 153-18-4
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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
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SUPRAMOLECULAR CHEMISTRY · 2017 · IF 1.264

A novel fluorescent indicator displacement assay for sensing the anticancer drug gefitinib

Yun-Yun Xi,Qing Tang,Ying Huang,Zhu Tao,Sai-Feng Xue,Qingdi Zhou,Gang Wei

Fluorescent indicator displacement assays have become popular for converting synthetic receptors into optical sensors. We have now shown that a 1:2 host–guest complex between cucurbit[8]uril (Q[8]) and proflavine (PF) can be used as a fluorescent indicator for sensing the anticancer drug gefitinib. The 2PF@Q[8] complex can be used to detect gefitinib with high selectivity using fluorescence spectrometry with a detection limit of 6.63 × 10−8 mol−L. The proposed sensing mechanism was investigated using 1H nuclear magnetic resonance spectroscopy (1H NMR), isothermal titration calorimetry and electrospray ionisation mass spectrometry. The 2PF@Q[8] complex was shown to be suitable for imaging gefitinib in prostate cancer (PC3) cells, which may help to elucidate relevant biological processes at the molecular level. We have developed a novel F-IDA to detect the anticancer drug GEF with high selectivity. The new indicator has excellent selectivity and a low detection limit for GEF. We have also demonstrated that the F-IDA can be used for the practical determination of drugs in living cells.

CAS / MDL: 184475-35-2
研究领域: 生物化学 · 药物分析 · 分子生物学
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JOURNAL OF MOLECULAR STRUCTURE · 2023 · IF 3.8

A cucurbit[8]uril-based fluorescent probe for the selective detection of pymetrozine

Pei-Hui Shan,Ding-Wu Pan,Li-Xia Chen,Timothy J. Prior,Carl Redshaw,Zhu Tao,Xin Xiao

Herein, we report a simple fluorescence-enhanced system for the selective recognition and determination of the insecticide pymetrozine. 1 H NMR spectroscopic data indicate that 1,2-bis(4-pyridyl)ethylene (BPE) is partially encapsulated in the cavity of the cucurbit[8]uril (Q[8]) in aqueous solution, forming a stable 1:2 host-guest inclusion complex. Good evidence is also provided by other characterization techniques including single crystal X-ray diffraction, UV–Vis and fluorescence spectroscopies. This host-guest inclusion complex shows weak fluorescence in aqueous solution. Interestingly, the addition of pymetrozine greatly enhanced the fluorescence of the host-guest inclusion complex. In contrast, no significant fluorescence enhancement was observed on addition of 10 other pesticides. The concentration of pymetrozine in aqueous solution was easily detected based on the linear relationship between fluorescence intensity and pymetrozine concentration. Therefore, this paper reports a new method to identify and determine pymetrozine by fluorescence enhancement.

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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.

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ACS Applied Materials & Interfaces · 2025 · IF 8.2

Supramolecular Combination Chemotherapy: Directly Inducing Immunogenic Cell Death To Inhibit Tumor Metastasis via Host–Guest Interactions

Qinye Liu,Xueting Sun,Yuanpeng Wang,Yueyue Chen

Tumor metastasis is a difficult clinical problem to solve due to tumor heterogeneity and the emergence of antiapoptotic clones driven by tumor evolution. Clinical combination chemotherapy remains a standard treatment for solid metastasis tumors but with worse treatment efficiency. It is worth exploring a high-efficiency and low-side-effect therapeutic method to solve solid metastases. Herein, we fabricate a supramolecular combination chemotherapeutic system based on host–guest interactions using a cucurbit[8]uril complex (CB[8]–lobaplatin–oxaliplatin, CLO). We explored whether CLO can induce colorectal cancer cell death by activating immunogenic cell death (ICD) to inhibit cancer cell migration in a safe and effective manner. CLO inhibits the viability of human colorectal cancer cells (HCT116) at only 10 μM and alleviates the cytotoxicity induced by lobaplatin–oxaliplatin (LO) in normal colorectal cells (NCM460). Interestingly, CLO can trigger ICD in colorectal tumor cells, and our results verified the upregulations of high mobility group box 1 (HMGB1) and adenosine triphosphate (ATP) release and cell surface calreticulin (CRT) exposure. Besides, we found that CLO can inhibit tumor migration both in vivo and in vitro, and bio-AFM characterization of tumor cellular surface also confirmed this phenomenon. To further investigate the underlying mechanisms of the antitumor effects of CLO, quantitative proteomics was employed, and the results indicated that the citrate cycle (TCA cycle), protein processing in the endoplasmic reticulum, cGMP-PKG signaling pathway, p53 signaling pathway, chemical carcinogenesis, and necroptosis signaling pathway might contribute to CLO-induced antitumor effects. Collectively, our study suggests that the supramolecular combination chemotherapeutic system based on CB[8] host–guest complex can activate ICD to inhibit metastasis in antitumor strategy and exhibits a remarkable potential for supramolecular immunotherapy.

研究领域: 肿瘤学 · 药理学 · 分子生物学
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