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JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS · 2022 · IF 3.571

Selective enrichment of microbiota-derived tryptophan metabolites in mouse faeces based on molecularly imprinted solid-phase extraction for HPLC analysis

Mengmeng Song,Xianjie Sheng,Genyi Ye,Zhuicheng Xu,Xinru Li,Tong Xie,Haishan Deng,An Kang

Gut microbiota-derived tryptophan (TRP) metabolites, especially the indole derivatives, function as critical modulators of intestinal immune function and integrity via modulating the aryl hydrocarbon receptor pathway. Selective enrichment of these indole metabolites in biological samples is important for quantitative determination by routine methods such as HPLC. Here, we report a molecularly imprinted polymer (MIP) for solid-phase extraction (SPE) of TRP-derived indole metabolites from faeces of mice. The MIP was synthesized by surface polymerization by using indole-3-acetic acid (IAA) and acrylamide after cross-linking by ethylene glycol dimethacrylate (EGDMA) and initialed by 2′,2-azobisisobutyronitrile (AIBN). The MIPs were then characterized by transmission electron microscope (TEM) and fourier transform infrared spectroscopy (FTIR), and the adsorption capacity, selectivity and reusability of MIPs were systematically evaluated. Results showed that IAA-MIPs showed a uniformly distributed nanoshell layer with a thin shell thickness of 26  nm . The IAA-MIPs could selectively adsorb IAA, indole-3-propionic acid (IPA), and indole-3-lactic acid (ILA) in a mixed solution that also contains TRP and tyrosine. The adsorption capacity of IAA-MIPs only slightly decreased with the increase of recycling use. As purification material for SPE, the IAA-imprinted polymers (IAA-MIPs) were successfully applied to extract IAA, IPA, and ILA from normal and colitis mice for HPLC determination. Collectively, these surface molecularly imprinted polymers could find extensive use to selective enrichment of microbiota-derived indole metabolites in biological samples.

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ANALYTICAL AND BIOANALYTICAL CHEMISTRY · 2022 ·Vol. 414 ·期 6 ·2275-2284 · IF 4.478

Distinguish oral-source VOCs and control their potential impact on breath biomarkers

Ge Dianlong,Zhou Jijuan,Chu Yajing,Lu Yan,Zou Xue,Xia Lei,Liu Yawei,Huang Chaoqun,Shen Chengyin,Zhang Liwei,Wang Huanzhong,Chu Yannan

By means of glass bottle sampling followed by solid-phase microextraction gas chromatography-mass spectrometry (SPME-GC-MS) technique, the change characteristics of volatile organic compounds (VOCs) in breaths, between before gargling and after gargling, were investigated, respectively, in 41 healthy subjects and 50 esophageal cancer patients. Using an untargeted strategy, 143 VOC chromatographic peaks were enrolled in the statistical analysis. Based on the orthogonal partial least squares discriminant analysis (OPLS-DA), the VOC variations after gargling for each breath test group were obtained according to the combined criteria of variable importance in projection (VIP > 1.5), Wilcoxon signed-rank test ( P < 0.05), and fold change (FC > 2.0). When gargled, the levels of indole, phenol, 1-propanol, and p-cresol in the breath of healthy people decreased; meanwhile, for esophageal cancer patients, the declined VOCs in breath were indole, phenol, dimethyl disulfide, and p-cresol. Particularly, these substances were previously reported as breath biomarkers in some diseases such as esophageal, gastric, thyroid, breast, oral, and lung cancers, as well as certain non-cancer disorders. The present work indicates that expiratory VOCs involve the prominent oral cavity source, and in the breath biomarkers study, the potential impact that originates from oral volatiles should be considered. In view of the present results, it is also proposed that gargle pretreatment could eliminate possible interference from the oral cavity VOCs that might benefit breath biomarker investigation. Graphical abstract Gargle pretreatment helps to distinguish oral-source VOCs and control their potential impact on breath biomarkers

CAS / MDL: 106-44-5 120-72-9
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ENVIRONMENTAL RESEARCH · 2022 · IF 8.431

Indole metabolism by phenol-stimulated activated sludges: Performance, microbial communities and network analysis

Jing Yang,Fang Ma,Chunxiao Dai,Weize Wu,Shuling Fan,Shengyang Lian,Yuanyuan Qu

Indole and phenol often coexist in the coking wastewater, while the effects of phenol on microbial communities of indole metabolism were less explored. In this study, the microbial interactions within activated sludge microbial communities stimulated by indole (group A) or by indole and phenol (group B) were systematically investigated in sequencing batch reactors (SBRs). The results showed that the removal of indole was increased by adding phenol. By using high-throughput sequencing technology, it was found that α-diversity was reduced in both groups. According to the relative abundance analysis, the indole-degrading genus Comamonas was the core genus in both groups (33.94% and 61.40%). But another indole-degrading genus Pseudomonas was only enriched in group A with 12.22% relative abundance. Meanwhile, common aromatic degrading genus Dyella and Thermomonas were enriched only in group B. It was found that the relative abundance of cytochrome P450 and styrene degradation enzymes were increased in group B by PICRUSt analysis. Based on the phylogenetic molecular ecological networks (pMENs), module hub OTU_1149 ( Burkholderia ) was only detected in group B, and the positive interactions between the key functional genus Burkholderia and other bacteria were increased. This study provides new insights into our understanding of indole metabolism communities stimulated by phenol, which would provide useful information for practical coking wastewater treatment.

CAS / MDL: 120-72-9
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Solar RRL · 2021 ·Vol. 6 ·期 4 ·2100995 · IF 8.582

5-Chloroindole as Interface Modifier to Improve the Efficiency and Stability of Planar Perovskite Solar Cells

Chunyan Wang,Jihuai Wu,Shibo Wang,Zhongliang Yan,Xuping Liu,Guodong Li,Liqiang Chen,Sijia Zhu,Weihai Sun,Zhang Lan

Interface engineering has been proven to be an effective method to improve the performance and stability of perovskite solar cells (PSCs). Herein, 5-chloroindole (Cl-indole) is introduced into the interface of a SnO 2 electron transport layer and perovskite light-absorbing layer to improve the photovoltage performance of the device. The results show that Cl−indole can not only form hydrogen bonds with iodine in the perovskite to optimize the interface contact but also coordinate and passivate the Pb 2+ and Sn 4+ interface defects to alleviate carrier nonradiative recombination. Compared with the pristine SnO 2 -based planar PSCs with a power conversion efficiency (PCE) of 20.58%, the Cl−indole-modified SnO 2 -based device achieves a PCE of 22.47%. Meanwhile, the stability of the modified device is effectively improved and the hysteresis effect is reduced. This work demonstrates a promising strategy for high-efficient and stable PSCs by optimizing interface contact and passivating interface defects.

CAS / MDL: 17422-32-1 120-72-9
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SEPARATION AND PURIFICATION TECHNOLOGY · 2021 · IF 7.312

Highly efficient extraction of indole from model wash oil by using environmentally benign deep eutectic solvents

Xudong Zhang,Junyao Wang,Jun Shen,Yugao Wang,Gang Liu,Yanxia Niu,Qingtao Sheng

Indole is an important organic synthesis intermediate derived from the wash oil fraction in coal tar. Deep eutectic solvents (DESs) have been widely used in the separation field due to their unique properties such as easy preparation, low cost, green and high extraction efficiency, and reusability. In this study, five DESs, including tetramethylammonium chloride/ethylene glycol (TMAC/EG), triethylmethylammonium chloride/ethylene glycol (TEMAC/EG), tetraethylammonium chloride/ ethylene glycol (TEAC/EG), tetrapropylammonium chloride/ethylene glycol (TPAC/EG), tetrabutylammonium chloride /ethylene glycol (TBAC/EG) were prepared and used to extract indole from model wash oil. The results showed that TPAC/EG exhibited the best extraction ability under the same conditions. Then, the main experimental parameters such as mass ratio of DES to model wash oil, extraction temperature, extraction time, standing time and initial concentration of indole, were investigated when using TPAC/EG as extractant. In optimal conditions (25℃, 5 min, mass ratio 1:8), the extraction efficiency, selectivity and distribution coefficient for indole were 90.51%, 79.21% and 61.12, respectively. Moreover, removing neutral oil with petroleum ether, the purity of indole further reached 96.63%, which was much higher than that in the previous studies reported. In addition, accessible and environmentally friendly water instead of diethyl ether was used to regenerate the DES. Reused four times, the TPAC/EG extraction ability for indole almost did not change. Finally, the mechanism of extraction process was investigated by FT-IR analysis. This work provides a new route for extraction and recovery indole from wash oil.

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Polymer Chemistry · 2023 ·Vol. 14 ·期 27 ·3166-3174 · IF 4.6

Poly (aryl sulfone)s containing 5,11-dihydroindolo[3,2-b] carbazole moieties in the main chain: non-conjugated blue-light-emitting materials

Yumiao Su,Wenmu Li

Three types of non-conjugated homopolymer with blue light emission containing 5,11-dihydroindolo[3,2-b]carbazole derivatives in the main chain were prepared via an N–C coupling reaction. Compared with the conjugated small molecule 5,11-dihydroindolo[3,2-b]carbazole derivatives, the emission spectra showed a blue shift after the introduction of nonconjugated diphenyl sulfone as the electron-deficient unit. Meanwhile, the rigid and twisted configuration of the polymers possesses the characteristic of large steric hindrance, which can effectively avoid the aggregation-caused quenching (ACQ) phenomenon in the solid state. From a test of the redox potential and DFT calculations of the small molecular monomers and polymers, the electron distribution and the molecular orbital (HOMO–LUMO) change of 5,11-dihydroindolo[3,2-b]carbazole derivatives with the introduction of electron-withdrawing and electron-donating units was revealed. The non-conjugated polymers exhibited excellent thermal stability and solubility, endowing them with good application prospects. The resultant polymers with different side groups showed blue light emission spectra from 427 nm to 461 nm. This facile and versatile strategy to synthesize non-conjugated polymers with blue light-emission leads to a new avenue for highly efficient and stable blue OLEDs.

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Journal of Cleaner Production · 2021 · IF 9.297

Octamolybdates containing MoV and MoVI sites supported on mesoporous tin oxide for oxidative desulfurization of liquid fuels

Antony Rajendran,Hong-Xia Fan,Tian-You Cui,Jie Feng,Wen-Ying Li

SO x emission, one of the significant contributors to air pollution, is primarily caused by the combustion of sulfur-containing liquid fuels . Thus, ultra-low sulfur or sulfur-free fuels production gains more attention to construct the SO x -free environment. Despite the oxidative desulfurization using polyoxometalates and hydrogen peroxide showing promising results, the requirement of hydrogen peroxide in excess and the complicated synthesis of heterogeneous polyoxometalates are the key drawbacks. So, in this paper, facile hydrothermal synthesis of mesoporous tin oxide-supported octamolybdates containing Mo V and Mo VI sites is reported for oxidative desulfurization with near stoichiometric hydrogen peroxide. The current catalytic system seems competitive among molybdenum-based oxidative desulfurization catalysts due to its higher turnover frequencies of 28.1 h −1 . The straightforward synthesis of catalysts and their excellent oxidative desulfurization activity would be attractive in building the SO x -free environment via clean transport energy.

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POLYMER INTERNATIONAL · 2023 · IF 3.2

A toughening indole-based epoxy film with efficient anti-counterfeiting properties driven by cation–π interaction

Qiaolin Tang,Lu Yuan,Ming Kang,Ying Huang,Li Yang,Qiang Yin,Guanjun Chang

A strong and tough indole-based epoxy film driven by cation– π interaction is designed, evading the trade-off between stiffness and extensibility in epoxy resins. The film with high strength, toughness and effective anti-counterfeiting properties induced by cation– π interaction is promising in the development of the fields of aerospace and electronic devices. © 2023 Society of Industrial Chemistry.

CAS / MDL: 1675-54-3 120-72-9
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Arabian Journal of Chemistry · 2023 · IF 6

Theoretical insight and experimental exploration of indole extraction from wash oil with deep eutectic solvents

Lan Yi,Xiaoqin Wu,Shuguang Ouyang,Li Guo,Jialing Chen,Mario Gauthier,Wen-Ying Li

The extraction of indole from wash oil is of economic value and practical significance. In this study, deep eutectic solvents (DESs) are investigated to extract indole from wash oil. Initially, density functional theory calculations were used to explore the association of indole with aromatic compounds in wash oil, and the feasibility of indole extraction with a tetraethylammonium chloride/ p -toluenesulfonic acid (TEAC/2TsOH) DES. Then, the influence of the temperature, stirring time, DESs dose, initial indole concentration, and amount of water added were investigated, followed by discussions on the comparison with other extractants and the performance of extracting of indole from real wash oil. The results show that indole associates with aromatic compounds in wash oil through π−π interactions, but that a large electrostatic interaction energy of −52.8 kJ/mol between indole and the DESs is the main driving force for the extraction process. Under optimal conditions, TEAC/2TsOH extracts more than 63.5 ± 3% of indole from wash oil, and its extraction capacity is superior to other extractants.

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FUEL · 2023 · IF 7.4

N-N self-inhibition effect of aromatic N-heterocyclic compounds on NiWS supported γ-Al2O3 hydrotreating catalyst

Wenbin Huang,Qiang Wei,Haoran Liu,Han Yang,Zhen Xu,Zhengyu Chen,Dongdong Chen,Yasong Zhou

The reason for high-difficulty nitrogen removal of aromatic N-heterocyclic compounds in petroleum fractions was investigated from the main thought of “NiWS property - Reaction behavior - DFT calculation”. The properties of the used catalyst were characterized by a series of techniques with the aim of providing the basis for model construction in the DFT calculations. The kinetic experiments in fixed-bed reactor revealed that although 1,2,3,4-tetrahydroquinoline (THQ1) and decahydroquinoline (DHQ), o-ethylaniline (OEA) exhibited relatively high yields in the HDN reaction of quinoline and indole respectively, they were all able to show high conversions and HDN rates when reacted as feedstocks alone. The study of product normalizations in the reaction system of the mixed feedstocks demonstrated that the difficulty of conversion of THQ1 and DHQ in quinoline HDN was mainly due to the inhibition effect of quinoline feedstock. While in the HDN of indole, the presence of the intermediate product OEA was the main factor for the low conversion of indole. This phenomenon of inhibition originating from within the molecular reaction network was proposed as N-N self-inhibition effect for the first time. The DFT calculations suggested that the inhibition of quinoline on THQ1 could be attributed to the adsorption advantage of quinoline, while the inhibition on DHQ was mainly due to the steric hindrance effect of DHQ itself. And the inhibition effect of OEA on indole can be mainly attributed to its greater nucleophilicity and stronger adsorption ability on the active sites compared with IND.

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JOURNAL OF MOLECULAR LIQUIDS · 2024 · IF 5.3

Mechanism exploration of deep eutectic solvents extraction of indole in wash oil

Lan Yi,Zhihao Cheng,Shisen Lv,Hao Luo,Jialing Chen,Li Guo,Xiaoqin Wu,Wen-Ying Li

Deep eutectic solvents (DESs) have gained significant interest for extracting indole from wash oil due to their exceptional characteristics and excellent extraction performance. An in-depth comprehension of the intermolecular interactions within the DES-wash oil system is crucial for developing principles that can guide the design of highly efficient DESs for indole extraction. The intermolecular interactions, molecular associations , and density profile in the DES-wash oil system were investigated using molecular dynamics simulation and FT-IR/ 1 H NMR characterization. The DES was composed of tetraethylammonium chloride and glycerol (TEAC/GLY), which was selected based on its exceptional experimental performance. Both the simulation and spectra results show that indole has strong hydrogen bond with TEAC/GLY. The hydrogen bond promotes indole extraction while van der Waals interactions cause aromatics entrainment. The components in wash oil exhibit two distinct molecular associations before and after the extraction of indole. A well-defined interface is established between the wash oil molecules and DES components, and indole has a preference for accumulating at the interface. The results provide an insight into the mechanism of extracting indole from wash oil using DES .

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PLoS Genetics · 2021 ·Vol. 17 ·期 7 ·e1009527 · IF 5.917

Identification of a gustatory receptor tuned to sinigrin in the cabbage butterfly Pieris rapae

Jun Yang,Hao Guo,Nan-Ji Jiang,Rui Tang,Guo-Cheng Li,Ling-Qiao Huang,Joop J. A. van Loon,Chen-Zhu Wang

Glucosinolates are token stimuli in host selection of many crucifer specialist insects, but the underlying molecular basis for host selection in these insects remains enigmatic. Using a combination of behavioral, electrophysiological, and molecular methods, we investigate glucosinolate receptors in the cabbage butterfly Pieris rapae . Sinigrin, as a potent feeding stimulant, elicited activity in larval maxillary lateral sensilla styloconica, as well as in adult medial tarsal sensilla. Two P . rapae gustatory receptor genes PrapGr28 and PrapGr15 were identified with high expression in female tarsi, and the subsequent functional analyses showed that Xenopus oocytes only expressing PrapGr28 had specific responses to sinigrin; when ectopically expressed in Drosophila sugar sensing neurons, PrapGr28 conferred sinigrin sensitivity to these neurons. RNA interference experiments further showed that knockdown of PrapGr28 reduced the sensitivity of adult medial tarsal sensilla to sinigrin. Taken together, we conclude that PrapGr28 is a gustatory receptor tuned to sinigrin in P . rapae , which paves the way for revealing the molecular basis of the relationships between crucifer plants and their specialist insects. Preference of crucifer specialist insects to glucosinolates is well known in the field of insect-plant interactions, but its molecular basis is unclear. This study uses an integrative approach to investigate the molecular basis of glucosinolate detection by gustatory receptor neurons in the larval mouthparts and adult forelegs of the cabbage butterfly Pieris rapae , and finally reveal that PrapGr28 is a bitter receptor tuned to sinigrin. The current work takes a significant step towards identifying gustatory receptors tuned to glucosinolates, crucial recognition signals in crucifer host plants, providing insights into co-evolution of herbivorous insects and their host plants.

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