SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2021
·
IF 4.098
Qin Wang,Li-Bing Lü,Zhu Tao,Tao Sun,Qing Tang,Ying Huang
In the present work, we have investigated the effect of pH and mercury ions on the host–guest complex formed between cucurbit[7]uril (Q[7]) and Hoechst 33342 (H33342). 1 H NMR, UV–vis and fluorescence spectroscopy revealed that acid/base stimulation could change the binding stoichiometry between Q[7] and H33342. The results suggest that two complexation equilibria (1:1 and 2:1) may exist between H33342 and Q[7] at pH 2.0 and 4.5, respectively. However, a 1:1 host–guest complex was formed between H33342 and Q[7] at pH 7.0 and 10.0. Q[7] shows differential affinities for the protonated and neutral forms of H33342 dye. Moreover, the switching between H33342∙2H + @2Q[7](1:2) at pH 4.5 and H33342∙H + @Q[7](1:1) at pH 7.0 was reversible. Furthermore, as a metal stimulus, Hg 2+ ions could push (i) Q[7] from the piperazine ring to the benzimidazole position with a 1:1 guest–host ratio and (ii) a second Q[7] onto the ethyl position with a 1:2 guest–host stoichiometry. This stimulus response system will have potential applications in the field of molecular switch design.
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高影响因子
INORGANIC CHEMISTRY COMMUNICATIONS
·
2019
·
IF 1.795
Mei-Xiang Yang,Ming Liu,Mei Yang,Qin Wang,Xi Zeng,Zhu Tao,Xin Xiao,Ying Huang
In the present work, a well-known host–guest inclusion complex comprising a cucurbit[7]uril (Q[7]) and an important biological dye, Hoechst-33258 (H33258) was selected as a fluorescence probe. In contrast to the pH conditions in which H33258 is exhibited in the literature, these being, mono- or di-protonated states, in the present work, we selected an extreme case, whereby H33258 was displayed in an anionic state (pH = 11). The investigation of the host–guest interaction demonstrated similar inclusion modes in a wide pH range, that is the dumbbell-like inclusion complex in which one Q[7] includes piperazine moiety and another Q[7] includes the phenol moiety of H33258. Moreover, investigation on the binding capacity of the 15 selected anions under three representative pH levels (pH = 2, pH = 4.5 and pH = 11, respectively) indicated that the H33258@Q[7] probe displayed unique selectivity on HPO 4 2 − anion in medium at pH = 11. More importantly, the probe could open a new platform in Q[ n ]-chemistry, that is the Q[ n ]-based host–guest interaction systems can apply in anion recognition or response.
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INTERNATIONAL JOURNAL OF PHARMACEUTICS
·
2024
·
IF 5.3
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.
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高影响因子
MOLECULAR PHARMACEUTICS
·
2023
·
IF 4.9
Wen-Juan Ma,Hua-Yu Chen,Yong-Liang Huang,Jia-Mei Chen,Tong-Bu Lu
This study is designed to compare drug encapsulation by cucurbit[7]uril and β-cyclodextrin, using fluorofenidone as a model drug. Single-crystal X-ray diffraction analysis was employed to successfully determine the crystal structures of fluorofenidone·H+@cucurbit[7]uril Form, fluorofenidone@cucurbit[7]uril Form, and fluorofenidone@β-cyclodextrin Form. Keto–enol tautomerization of fluorofenidone mediated by cucurbit[7]uril in acid solution is confirmed by crystal structures, pH titration, and nuclear magnetic resonance experiments. However, β-cyclodextrin cannot cause the keto–enol tautomerization of fluorofenidone under similar conditions. The phase solubility study demonstrates that cucurbit[7]uril has a much higher solubilization capacity for fluorofenidone than β-cyclodextrin in 0.1 M HCl since the Kc values of fluorofenidone with cucurbit[7]uril and β-cyclodextrin were 1223.97 ± 452.68 and 78.49 ± 10.56 M–1, respectively. Excellent solubility can be attributed to the keto–enol tautomerization of fluorofenidone under the conditions of cucurbit[7]uril in acid solution. The enol form of fluorofenidone is encapsulated by cucurbit[7]uril by hydrogen bonding interaction and hydrophobic interaction to increase binding affinity. Rat pharmacokinetic studies demonstrate that the area under the plasma concentration–time curve from time 0 to 7 h value of fluorofenidone@cucurbit[7]uril complex is 1.70-fold greater than that of free fluorofenidone, and the mean residence time from time 0 to 7 h is slightly prolonged from 1.29 to 1.76 h (P < 0.01) after oral administration. However, no significant difference is found between fluorofenidone and fluorofenidone@β-cyclodextrin complex. This work indicates that the induction of keto–enol tautomerization of drugs using macrocyclic molecules has the potential to be an effective method to improve their solubility and bioavailability, providing valuable insights for the application of macrocyclic molecules in the biomedical field.
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Journal of Cleaner Production
·
2024
·
IF 9.7
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.
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Advanced Optical Materials
·
2024
·Vol. 12
·期 23
·2400839
·
IF 8
Xiao-Feng Wang,Rui-Lian Lin,Wen-Qi Sun,Jing-Xin Liu,Li-Xin Xu,Carl Redshaw,Xing Feng
Multistimuli-responsive color-changing materials have potential applications in areas such as chemical sensing and anti-counterfeiting. In this work, a fluoro-phenyl-acetyl-substituted viologen derivative (FPAV·Cl 2 ) is synthesized, which can form a supramolecular inclusion complex with cucurbit[7]uril (Q[7]) via self-assembly. Significantly, the resulting inclusion complex FPAV 2+ @Q[7] in the solid-state exhibits visual color changes in response to multiple external stimuli including light, heat, and vapors of ammonia and organic amines. The electron spin resonance (ESR) and ultraviolet–visible (UV–vis) spectra analysis reveals that the photochromic, thermochromic, and vapochromic behavior of FPAV 2+ @Q[7] is due to the generation of FPAV +• free radicals resulting from electron transfer. Furthermore, in the solid-state, FPAV 2+ @Q[7] shows controllable fluorescence regulated by its chromic process. Based on the multi stimuli-responsive color-changes and fluorescence properties of FPAV 2+ @Q[7], its practical applications in erasable inkless printing, multiple anti-counterfeiting processes, visible ammonia/organic amines detection, and information encryption are demonstrated. The supramolecular strategy of encapsulating viologen derivatives into macrocycles provides a general method for fabricating multi stimuli-responsive chromic materials with multiple practical applications.
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ChemSusChem
·
2019
·Vol. 13
·期 2
·394-399
·
IF 7.804
Dengmeng Song,Bo Li,Xin Li,Xuzhuo Sun,Jun Li,Chengbo Li,Tongyu Xu,Yong Zhu,Fei Li,Ning Wang
Graphical Get in or get out : A cobaloxime catalyst and Eosin Y photosensitizer were assembled with macrocyclic cucurbit[7]uril through inclusion and exclusion interactions, respectively. The synchronous self-assembly drove an orthogonal arrangement of the ternary system with significant spatial proximity. The ternary supramolecular system showed better performance for photocatalytic H 2 evolution than multicomponent systems. The fabrication of efficient and convenient photocatalytic H 2 evolution systems is a fascinating research topic in the field of solar energy conversion. A ternary self-assembled photocatalytic H 2 evolution system was fabricated through supramolecular host–guest chemistry. The system consisted of the H 2 evolution catalyst [Co(dmgH) 2 (4-ppy) 2 ]NO 3 ( 1 ; dmgH 2 =dimethylglyoxime, 4-ppy=4-phenylpyridine) and the photosensitizer Eosin Y (EY) assembled with the macrocyclic compound cucurbit[7]uril (CB[7]) to form the 1 @CB[7]/EY complex through inclusion and exclusion interactions, respectively. The synchronous self-assembly drives an orthogonal arrangement of the 1 @CB[7]/EY system. The inclusion complex 1 @CB[7] was successfully characterized by 1 H NMR spectroscopy and single-crystal XRD. The exclusion process of CB[7] with EY was identified by NMR titration and the optimized geometry of the exclusion structure was determined by DFT calculations. The use of CB[7] resulted in a 6-fold increase in turnover number, a 3-fold increase in turnover frequency, and a 3-fold extension of lifetime for photocatalytic H 2 evolution as compared with the system in the absence of CB[7]. The improvement of the light-driven H 2 evolution activity was ascribed to the ability of CB[7] to link the photosensitizer and catalyst.
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CHEMICAL ENGINEERING JOURNAL
·
2024
·
IF 13.3
Dong-Xue Xia,Xin Wang,Wen-Qi Sun,Rui-Lian Lin,Jing-Xin Liu,Ying-Wei Yang
Inspired by Chameleons' skin color tuning in response to environmental changes, we design and prepare three inclusion complexes based on the cucurbit[7]uril (Q[7]) host and three viologen guests. Upon light irradiation, the colors of these inclusion complexes in the solid state turn from light colors to vivid three primary colors, i.e., red, green, and blue, respectively. Ultraviolet–visible (UV–vis) diffuse reflectance and electron spin resonance (ESR) spectra reveal that the photochromism can be attributed to the generation of viologen radicals, originating from the photoinduced electron transfer. The results of quantum chemical calculation indicate that Q[7] in the inclusion complexes acts as the electron donor in the photoinduced electron transfer process. Using a color mixing approach and finely manipulating the proportions of the three inclusion complexes, a series of composite photochromic materials (CPMs) can be manufactured, covering a full-color gamut in visible light. On the other hand, due to the ignorable size and shape change of CPMs during the photochromatic processes, the CPMs-based reversible photochromic “printing” and photofading “erase” properties were also used for quick response (QR) code. Therefore, these prominent intelligent features of CPMs open new avenues to explore optical regulated nano-platforms for multiple anti-counterfeiting, biomimetics, and military camouflage applications.
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DYES AND PIGMENTS
·
2020
·
IF 4.613
Guangliang Hou,Shenxi Min,Yuhan Zhao,Bin Dong,Lina Zhang,Dahua Li,Weichun Wu,Huifang Zhu,Bo Song
In this study, we synthesized an amphiphilic α-cyanostilbene derivative ( E -form)-1-(12-(2-(2-(benzo[d]thiazol-2-yl)-2-cyanovinyl)-5-(diethylamino)phenoxy)dodecyl)pyridin-1-ium bromide (denoted by BCPB). As being dissolved in aqueous solution, BCPB shows strong emission of excimers at around 660 nm due to the formation of aggregates. Addition of different amount of CB[7] into the solution leads to the emission shift from 660 nm, firstly to 540 nm and then to 588 nm. The emission shift is attributed to the two-step assembly driven by the concentration of CB[7], and the molar ratios of CB[7]/BCPB (denoted by R m ) play a critical role for the shift. As R m ≤ 4, CB[7] mainly interacts with the cationic pyridinium group of BCPB to form BCPB@CB[7] complex. As R m > 4, another CB[7] binds to the diethylamino group at one end of α-cyanostilbene to form BCPB@CB[7] 2 complex. The two-step assembly well explains the emission shift of BCPB.
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ANALYTICAL CHEMISTRY
·
2024
·
IF 6.7
Qiuxiang Mao,Lancheng Wang,Dandan Xue,Xiaoxuan Lin,Fang Sun,Pengcheng Xu,Jieru Chen,Wenying Li,Xiuchen Li,Fang Yan,Chi Hu
Although multiple forms of dimers have been described for GPCR, their dynamics and function are still controversially discussed field. Fluorescence microscopy allows GPCR to be imaged within their native context; however, a key challenge is to site-specifically incorporate reporter moieties that can produce high-quality signals upon formation of GPCR dimers. To this end, we propose a supramolecular sensor approach to detect agonist-induced dimer formation of μ-opioid receptors (μORs) at the surface of intact cells. With the macrocyclic host cucurbit[7]uril and its guest hemicyanine dye tethered to aptamer strands directed against the histidine residues, the sensing module is assembled by host–guest complexation once the histidine-tagged μORs dimerize and bring the discrete supramolecular units into close proximity. With the enhanced sensitivity attributed by the “turn-on” fluorescence emission and high specificity afforded by the intermolecular recognition, in situ visualization of dynamic GPCR dimerization was realized with high precision, thereby validating the supramolecular sensing entity as a sophisticated and versatile strategy to investigate GPCR dimers, which represent an obvious therapeutic target.
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Aggregate
·
2025
·
IF 13.7
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.
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RSC Advances
·
2015
·Vol. 5
·期 81
·65775-65779
·
IF 3.84
Rui Han Gao,Ying Fan,Bo Xiao,Peng Chen,Jian Xin Zhang,Qing-di Zhou,Sai Feng Xue,Qian Jiang Zhu,Zhu Tao
A one-pot strategy was employed to synthesize a series of water-soluble cucurbit[7]uril-anchored polyacrylic acids (Q[7]-anchored PAAs) with high yields in the presence of an ammonium persulfate salt as both an initiator and an oxidant. The effects of acrylic acid, Q[7] feed mass and APS concentration on the formation of polymer nanocapsules have been investigated. The Q[7]-anchored PAAs can be further esterified with 2-naphthol to yield water-insoluble derivatives, which are characteristic of the stationary phase for absorption of basic dyes, especially neutral red.
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