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Cucurbit[7]Uril
JOURNAL OF APPLIED ELECTROCHEMISTRY · 2022 ·Vol. 53 ·期 5 ·1023-1032 · IF 2.925

Sensitive detection of barium ion based on its enhancing effect on luminol electrochemiluminescence at cucurbit[7]uril-modified electrode

Luo Yuhua,Yao Haifeng,Zhang Yahui,Dong Yongping

Abstract In this paper, a sensitive electrochemiluminescence (ECL) method for the detection of Ba 2+ was proposed based on its apparent enhancing effect on the anodic luminol ECL at a cucurbit[7]uril (Q[7])-modified glassy carbon electrode (Q[7]/GCE). The cavity of the modified Q[7] could accommodate more dissolved oxygen at the electrode surface which reacted with luminol to generate strong anodic ECL signal compared with a bare GCE. Ba 2+ ions exhibited further enhancing effect on luminol ECL when they were immobilized at the portal of Q[7] through chelating with carbonyl group of Q[7]. The increment of ECL signal varied linearly with the concentration of Ba 2+ , as a result, an ECL sensor for the quantitative detection of Ba 2+ was constructed. Under the optimal condition, Ba 2+ could be sensitively detected in the range of 1.0 × 10 –7 to 1.0 × 10 –4  mol L −1 , and the detection limit was calculated as 10 nM (3σ). The proposed ECL sensor exhibited satisfactory analytical performance and could be used in real samples analysis, which provided a new strategy for metal ions detection. Graphic abstract The encapsulation of dissolved oxygen by Q[7] can enrich oxygen concentration at the electrode surface, which can react with luminol to emit enhanced ECL. The presence of Ba 2+ can increase the amount of O2 •- at the electrode surface through the formation of barium-peroxide species, which can further enhance luminol ECL. Thus, an ECL sensor for the sensitive detection of Ba 2+ was built.

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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.

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ACS Omega · 2018 · IF 0

4-Sulfocalix[4]arene/Cucurbit[7]uril-Based Supramolecular Assemblies through the Outer Surface Interactions of Cucurbit[n]uril

Xiao Tian,Li Xia Chen,Yu Qing Yao,Kai Chen,Min-Dong Chen,Xi Zeng,Zhu Tao

Upon mixing of aqueous solutions of the freely soluble building blocks cucurbit[7]uril (Q[7]) and 4-sulfocalix[4]arene (SC[4]A), white microcrystals instantly separate in near-quantitative yield. The driving force for this assembly is suggested to be the outer-surface interaction of the Q[n]. Dynamic light scattering, scanning electron microscopy, and NMR (diffusion-ordered NMR spectroscopy) analyses have confirmed the supramolecular aggregation of Q[7] and SC[4]A. Titration 1H NMR spectroscopy and isothermal titration calorimetry have shown that the interaction ratio of Q[7] and SC[4]A is close to 3:1. Moreover, the Q[7]/SC[4]A-based supramolecular assembly can accommodate molecules of some volatile compounds or luminescent dyes. Thus, this work offers a simple and highly efficient means of preparing adsorbent or solid fluorescent materials.

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Analytical Methods · 2021 ·Vol. 13 ·期 36 ·4090-4098 · IF 2.896

An “on–off” fluorescent probe based on cucurbit[7]uril for highly sensitive determination of ammonia nitrogen in aquaculture water

Zhen Li,Tan Wang,Xianbao Xu,Cong Wang,Daoliang Li

A novel “on–off” fluorescent probe was synthesized for highly sensitive and ultra-trace determination of ammonia nitrogen in aquaculture water. Ammonium can react with formaldehyde and sodium hydroxide to form a ring substance (urotropine), which shows no fluorescence signal. Palmatine hydrochloride (PAL) can enter the hydrophobic cavity of cucurbit[7]uril (CB[7]), eventually forming a 1 : 1 host guest complex called PAL@CB[7] under neutral or acidic conditions, which has strong green fluorescence with the maximum excitation (λex) wavelength at 343 nm, and the maximum emission (λem) wavelength at 500 nm, while urotropine has a fluorescence quenching effect on the fluorescence enhancement system of PAL@CB[7]. Therefore, a fluorescent chemosensor based on PAL@CB[7] and the reaction of ammonia nitrogen with formaldehyde was developed. The results indicate that the linearity range and the limit of detection of the proposed method are 1–300 μg L−1 with a good correlation coefficient (r2 = 0.9966) and 1.8 × 10−2 μg L−1, respectively. Under the optimal conditions, the method was employed for the detection of ammonia nitrogen in real aquaculture water samples, revealing high selectivity and sensitivity. In the future, the combination of the “on–off” fluorescence method, a portable hardware system and intelligent algorithms will provide technology support for the design of on-line sensors for measuring ammonia nitrogen in aquaculture water.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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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
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ANALYTICA CHIMICA ACTA · 2026 · IF 6.1

Molecular recognition-based affinity chromatography strategy for selective separation of cucurbit[5]uril and cucurbit[7]uril on hybrid monolithic materials

Xiaolong Shen,Ruizhi Tang,Shujuan Ma,Yangyang Bian,Zichao Tang,Junjie Ou

Background As a class of star macrocyclic molecules, cucurbit [n]urils (CB[n]) have gained extensive applications across multiple fields, including perovskite batteries, adsorption separation, room-temperature phosphorescence and biomolecular science and so on. The acquisition of high-purity CB[n] presents a significant challenge, especially for researchers without a dedicated background in organic synthesis and purification. The separation of individual CB[n] homologues is notoriously difficult, especially in the case of CB[7] and CB[5] due to their similar solubility and chemical properties. Therefore, development of specific and selective chromatographic methods is necessary for efficient separation of CB[n] homologues. Results In this work, three types of bipyridine-containing hybrid monolithic materials were designed and fabricated through “one-pot” approach, and then employed as an adsorption platform for the separation of CB[5] and CB[7] via supramolecular affinity chromatography strategy. This novel method offers efficient separation based on the differential molecular recognition mechanism of CB[5] and CB[7] toward the guest bipyridine moiety. Compared with the guests within the polymer chains, exposing the guests at the terminal ends of the adsorbent surface would benefit the specific adsorption capability of CB[7]. After optimizing the chromatographic conditions, the separation of CB[5] and CB[7] was successfully achieved on hybrid monolithic materials modified with 4,4′-bipyridine (Monolith-Ⅱ-Bp), enabling the isolation of 12 mg CB[5] and 10 mg CB[7] with high-purity from 40 mg of the crude product, corresponding to yields of 30.0% and 25.0%, respectively. Significance This work is the first to introduce hybrid monolithic materials and a separation strategy based on specific and reversible host-guest interactions, enabling simplified purification of CB[5] and CB[7] and accurate determination of their purity by MALDI-TOF MS. This approach is expected to serve as a reliable laboratory-scale method for the preparation of high-purity CB[n] homologues.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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TALANTA · 2021 · IF 6.057

A novel electrochemical aptasensor for exosomes determination and release based on specific host-guest interactions between cucurbit [7]uril and ferrocene

Qian Liu,Xinmin Yue,Yixian Li,Fang Wu,Meng Meng,Yongmei Yin,Rimo Xi

The superior supramolecular recognition ability of macrocyclic compounds will enhance the sensitivity and selectivity of electrochemical detection , which has a great application potential in electrochemical sensing. Herein, we developed a novel electrochemical aptasensor based on the specific host-guest interactions between cucurbit [7]uril and ferrocene (Fc) for capture, determination and release of exosomes. Macrocyclic compounds, cucurbit [7]uril is modified on the surface of the gold nanoparticles composed electrode by self-assembling. CD63 aptamer linked ferrocene is introduced into this platform to capture exosomes specifically by CD63 protein on the exosomes. The dual specificity of macrocyclic compounds and aptamers enables highly selective and sensitive electrochemical detection of exosomes. The limit of detection (LOD) was 482 particles μL -1 . In addition, the captured exosomes could be released on demand in a very mild manner through aminoferrocene (NH 2 -Fc) because of its higher affinity to cucurbit [7]uril. The proposed electrochemical aptasensor showed good performance in detecting exosomes even in plasma samples, thus demonstrating its great potential in early clinical diagnosis. Simultaneously, exosomes could be released undamaged by this protocol, exhibiting good applicability in comprehensive studies of exosomes. Moreover, this strategy can be applied to other target biomolecules by changing the recognition pairs.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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Scientific Reports · 2017 ·Vol. 7 ·期 1 ·1-10 · IF 4.259

An easy gene assembling strategy for light-promoted transfection by combining host-guest interaction of cucurbit[7]uril and gold nanoparticles

Du Jianwei,Zhang Peng,Zhao Xiao,Wang Youxiang

Cucurbit[7]uril (CB[7]), a representative member of the host family cucurbit[n]uril, can host-guest interact with many guest molecules such as adamantane, viologen and naphthalene derivatives. This host-guest interaction provides an easy strategy in gene vector assembling. Furthermore, CB[7] can self-assemble on gold nanospheres (AuNSs). Herein, the combination of CB[7] and AuNSs provides both advantages of host-guest interaction and photo-thermal effect of AuNSs. In this study, polyethyleneimine (PEI) and polyethylene glycol (PEG) were separately interacted with CB[7] via host-guest interaction. Then by assembling on AuNSs, PEI and PEG were combined together to condense DNA into polyplexes as well as enhance circulation stability of the polyplexes. These gene vectors were found to have high cellular uptake efficiency and low cytotoxicity. Furthermore, the well distributed AuNSs in the polyplexes could transform light into heat under light exposure because of the photo-thermal effect. This was found to effectively promote the entry of gene into cytoplasm and highly enhanced gene transfection efficiency.

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JOURNAL OF BIOMATERIALS APPLICATIONS · 2026 · IF 2.5

Zoledronic acid/cisplatin-loaded cucurbit[7]uril-modified upconversion nanoformulations drive tumor-associated macrophage polarization and potentiate the efficacy of cancer immunotherapy

Yakun Ge,Pengcheng Li,Jiatong Zhang,Ruolan Wang,Renwen Zhang,Hongyu Xu,Zhenming Hao,Yuanxin Zhang

Tumor-associated macrophages (TAMs) play a pivotal role in establishing a tumor immunosuppressive microenvironment (TIME) by inducing a phenotypic shift in macrophage from the pro-inflammatory M1 to the anti-inflammatory M2 phenotype. This polarization facilitates tumor growth, progression, metastasis, immune evasion, and chemoresistance. Consequently, reprogramming the TIME by repolarizing TAMs has emerged as a promising approach in cancer therapy. In this study, we synthesized core-shell structured nanoparticles (UCNPs@CB-Zol-Pt) utilizing host-guest interactions between NaYF4:Yb/Er (UCNPs) and cucurbit[7]uril (CB). These nanoparticles were designed to polarize M2-like macrophages into M1-like macrophages and release tumor-associated antigens (TAAs), thereby potentially inducing the release of immunogenic cell death (ICD). Furthermore, the M1-type macrophages could ingest, process, and present TAAs generated from platinum-based chemotherapy through MHC class II molecules. This process simultaneously enhances the infiltration of helper and effector T cells into the TIME, thereby potentiating the efficacy of checkpoint blockade immunotherapy.

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ANALYST · 2023 ·Vol. 149 ·期 4 ·1160-1168 · IF 4.2

Electrochemiluminescence of an iridium complex doped with SiO2 nanoparticles to detect 2-adamantanamine based on the host–guest interaction of cucurbit[7]uril

Yahui Zhang,Haifeng Yao,Yongping Dong

The poor solubility of iridium complexes severely hampers its application in the electrochemiluminescence (ECL) sensing field. The doping of an iridium complex with silica (SiO2) nanospheres provides feasible solution for this problem. Herein, one kind of water insoluble iridium complex ([Ir(dFppy)2(d(CF3)bpy)](PF6)) was doped with SiO2 nanoparticles to obtain a luminescent nanocomposite (SiO2@Ir) which could generate strong ECL signals to act as a beacon molecule. An “off–on–off” mode ECL sensor was proposed based on the competitive host–guest interactions between 2-adamantanamine (2-ADA), ferrocene (Fc) and cucurbit[7]uril (Q[7]). Fc could be used as an inhibitor to decrease the ECL signal, while Q[7] could wrap Fc to recover the ECL signal. Q[7] has a stronger binding ability with 2-ADA than Fc. As a result, 2-ADA could replace Fc from the cavity of Q[7], and the ECL signal was inhibited again. Under the optimal conditions, the ECL intensity varied linearly with 2-ADA concentration in the range of 1.0 × 10−8 to 1.0 × 10−6 mol L−1 with a detection limit of 2.5 × 10−10 mol L−1. The results not only provided a new avenue for the application of water insoluble iridium complexes in ECL sensing, but also revealed the attractive potential of host–guest interactions in the fabrication of biosensors.

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CHEMISTRY OF MATERIALS · 2014 · IF 8.535

Mesoporous Silica Nanoparticles Coated by Layer-by-Layer Self-assembly Using Cucurbit[7]uril for in Vitro and in Vivo Anticancer Drug Release

Qing-Lan Li,Yanfang Sun,Yu-Long Sun,Jijie Wen,Yue Zhou,Qi-Ming Bing,Lyle D. Isaacs,Yinghua Jin,Hui Gao,Ying-Wei Yang

Mesoporous silica nanoparticles (MSNs) are promising solid supports for controlled anticancer drug delivery. Herein, we report biocompatible layer-by-layer (LbL) coated MSNs (LbL-MSNs) that are designed and crafted to release encapsulated anticancer drugs, e.g., doxorubicin hydrochloride (DOX), by changing the pH or by adding competitive agents. The LbL coating process comprises bis-aminated poly(glycerol methacrylate)s (BA-PGOHMAs) and cucurbit[7]uril (CB[7]), where CB[7] serves as a molecular bridge holding two different bis-aminated polymeric layers together by means of host–guest interactions. This integrated nanosystem is tuned to respond under specific acidic conditions or by adding adamantaneamine hydrochloride (AH), attributed to the competitive binding of hydronium ions or AH to CB[7] with BA-PGOHMAs. These LbL-MSN hybrids possess excellent biostability, negligible premature drug leakage at pH 7.4, and exceptional stimuli-responsive drug release performance. The pore sizes of the MSNs and bis-aminated compounds (different carbon numbers) of BA-PGOHMAs have been optimized to provide effective integrated nanosystems for the loading and release of DOX. Significantly, the operating pH for the controlled release of DOX matches the acidifying endosomal compartments of HeLa cancer cells, suggesting that these hybrid nanosystems are good candidates for autonomous anticancer drug nanocarriers actuated by intracellular pH changes without any invasive external stimuli. The successful cellular uptake and release of cargo, e.g., propidium iodide (PI), in human breast cancer cell line MDA-231 from PI-loaded LbL-MSNs have been confirmed by confocal laser scanning microscopy (CLSM), while the cytotoxicities of DOX-loaded LbL-MSNs have been quantified by the Cell Counting Kit-8 (CCK-8) viability assay against HeLa cell lines and fibroblast L929 cell lines. The uptake of DOX-loaded LbL-MSNs by macrophages can be efficiently reduced by adding biocompatible hydrophilic poly(ethylene glycol) or CB[7] without destroying the capping. In vivo tumor-growth inhibition experiments with BALB/c nude mice demonstrated a highly efficient tumor-growth inhibition rate of DOX-loaded LbL-MSNs, suggesting that the novel type of LbL-MSN materials hold great potentials in anticancer drug delivery.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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BIOSENSORS & BIOELECTRONICS · 2022 · IF 12.545

Sensitive and selective detection of carbamazepine in serum samples by bionic double-antibody sandwich method based on cucurbit[7]uril and molecular imprinted polymers

Zhaorui Song,Xinhui Zhai,Chenrui Jiang,Rong Chen,Sijing Ye,Jinzhe Tong,Pierre Dramou,Hua He

A novel bionic enzyme-linked immunosorbent assay (BELISA) based on double-antibody sandwich method is firstly designed for the detection of carbamazepine (CBZ) in human serum samples. In this BELISA system, cucurbit[7]uril (CB[7]) is employed as an artificial capture antibody (cAb), and molecularly imprinted polymers (MIPs) is used as an artificial detection antibody (dAb). Nanozymes (PdNPs) as signal generators are integrated with MIPs. This couple of bionic antibodies exhibits not only the excellent physical and chemical stability, but also the superior molecular recognition ability. Based on two bionic antibodies that can selectively recognize different sites of CBZ molecule, a new BELISA method has been constructed for the first time. The proposed BELISA method displays a good linear relationship ranging from 2 to 20 μg mL -1 . The detection limit is 0.37 μg mL -1 , which can well meet clinical testing demand. It provides a more stable and economical method for clinical therapeutic drug monitoring (TDM).

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