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INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES · 2021 ·Vol. 22 ·期 11 ·5680 · IF 5.924

Design, Synthesis, and Biological Evaluation of Novel 6H-Benzo[c]chromen-6-one Derivatives as Potential Phosphodiesterase II Inhibitors

Long Tang,Jianchun Jiang,Guoqiang Song,Yajing Wang,Ziheng Zhuang,Ying Tan,Yan Xia,Xianfeng Huang,Xiaoqing Feng

Urolithins (hydroxylated 6H-benzo[c]chromen-6-ones) are the main bioavailable metabolites of ellagic acid (EA), which was shown to be a cognitive enhancer in the treatment of neurodegenerative diseases. As part of this research, a series of alkoxylated 6H-benzo[c]chromen-6-one derivatives were designed and synthesized. Furthermore, their biological activities were evaluated as potential PDE2 inhibitors, and the alkoxylated 6H-benzo[c]chromen-6-one derivative1fwas found to have the optimal inhibitory potential (IC50: 3.67 ± 0.47 μM). It also exhibited comparable activity in comparison to that of BAY 60-7550 in vitro cell level studies.Keywords:alkoxylated 6H-benzo[c]chromen-6-one;phosphodiesterase II;inhibitors;biological activities

研究领域: 药理学 · 有机化学 · 神经科学
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COLLOIDS AND SURFACES B-BIOINTERFACES · 2012 · IF 3.456

Fabrication of biodegradable micelles with reduction-triggered release of 6-mercaptopurine profile based on disulfide-linked graft copolymer conjugate

Xuzhu Zhang,Fang Du,Jin Huang,Wei Lu,Shiyuan Liu,Jiahui Yu

This research is aimed to develop a biodegradable micelle delivery system with sheddable poly (ethylene glycol) shell to achieve the reduction-triggered intracellular sustained release of 6-mercaptopurine (6-MP) and decreased toxicity. Firstly, the amino-disulfide linked poly (ethylene glycol) monomethyl ether (mPEG-SS-NH 2 ) was synthesized by the amidation reaction between cystamine and active ester of mPEG and p-nitrophenyl chloroformate (p-NPC) (mPEG–NPC). And then, the five-member rings in poly ( l -succinimide) (PSI) were successively opened by mPEG-SS-NH 2 and 2-(pyridyldithio)-ethylamine (PDA) to produce the graft copolymer of mPEG-SS-NH- graft -PAsp-PDA. To avoid the drug initial burst, 6-MP was covalently conjugated with mPEG-SS-NH- graft -PAsp-PDA by thoil–disulfide exchange reaction to give the resultant product mPEG-SS-NH- graft -PAsp-MP. The product was found to form spherical micelles in aqueous media because of its amphiphilic nature with average particle size of 160   nm measured by dynamic light scattering (DLS). It was found that the mPEG-SS-NH- graft -PAsp-MP micelles, though stable in phosphate buffer solution (PBS), were prone to aggregation in the presence of dithiothreitol (DTT). The in vitro drug release studies revealed the release of 6-MP were distinct from the conventional micelles whose drugs loaded by physical encapsulation. Sustained release profile of 6-MP over 85   h was found in the presence of DTT (40   mM) simulating the intracellular condition while minimal drug release was observed within 24   h at the level of DTT corresponding to extracellular environment. Remarkably, the cell viability results showed there was essential decrease of cytotoxicity to HL-60 cell line compared to free 6-MP.

研究领域: 药剂学 · 生物材料学 · 肿瘤学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2025 · IF 6.2

Streptomyces-Induced 6-Nitrocoumarin Coordinates Rhizosphere Microbiome Recruitment for Pepper Blight Suppression

Tianbing Zhou,Yuxin Xu,Yingtong Chen,Zhengbin Tang,Erxin Wang,Mengmeng Li,Mingrui Dou,Zhijia Zhang,Tao Zhang,Shujun Huang,Shuxian Gu,Shuai Wang,Ranfeng Sun,Dong Li

Phytophthora capsici causes devastating losses in global pepper production. This study deciphers a sophisticated plant-microbe-metabolite collaboration initiated by rhizosphere-colonizing Streptomyces. We demonstrate that Streptomyces specifically primes pepper root biosynthesis of 6-nitrocoumarin, a nitrated coumarin derivative exhibiting potent broad-spectrum antioomycete activity (EC50: P. capsici 44.39 mg/L, Phytophthora palmivora 47.06 mg/L, Peronophythora litchii 34.92 mg/L). Crucially, this Streptomyces-recruited metabolite functions as a keystone rhizosphere signal, selectively enriching beneficial bacterial consortia while directly disrupting the ABC transporters of pathogens. The restructured microbiome synergistically amplifies plant systemic resistance through upregulating defense genes and enhancing root immunity. Our work establishes 6-nitrocoumarin as a dual-functional inoculant, a direct actinomycete compound and microbiome modulator, revealing a novel plant-microbe codefense paradigm driven by Streptomyces-induced metabolic rewiring for sustainable crop protection.

CAS / MDL: 2725-81-7
研究领域: 植物病理学 · 微生物生态学 · 分子植物-微生物互作 · 农业生物技术 · 天然产物化学 · 作物保护 · 根际生物学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2025 · IF 8.5

Preparation of 6-gingerol loaded chitosan/polyvinyl alcohol active films and applications in the preservation of grouper fillets

Jiaqi Yuan,Huihui Liu,Jian Zhang,Jing Xie,Jun Yan

The limited shelf-life and vulnerability to microbial contamination of grouper fillets pose a pressing challenge. 6-gingerol exhibits both antimicrobial and antioxidant properties, which have the potential for application in food preservation. This study aimed to assess the antibacterial effect of 6-gingerol, prepare a 6-gingerol loaded CS/PVA active films, and evaluate the preservation effect on grouper fillets. Results indicated that the incorporation of 6-gingerol (1.8 mg/mL) significantly enhanced the elongation at break, antimicrobial, and antioxidant activities by 64.35 %, 72.85 %, and 87.13 %, respectively, compared to CS/PVA film. The total volatile basic nitrogen, thiobarbituric acid reactive substance, and the total sulfhydryl of grouper fillets on day 12 were reduced by 35.39 %, 38.96 %, and 36.52 %, respectively, along with improved sensory ratings. The shelf-life of grouper fillets was extended from 9 days to 12 days. This study provides a novel approach for preserving grouper fillets and the high-value utilisation of ginger, providing a valuable reference for developing natural active packaging materials with antimicrobial and antioxidant properties.

CAS / MDL: 56-81-5
研究领域: 食品科学 · 生物化学
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SENSORS AND ACTUATORS B-CHEMICAL · 2018 · IF 5.667

Highly reproducible and fast detection of 6-thioguanine in human serum using a droplet-based microfluidic SERS system

Wen-Shu Zhang,Ya-Ning Wang,Yue Wang,Zhang-Run Xu

6-thioguanine is an anticancer drug with narrow safe dose range and intense toxic reactions, so it is urgently necessary to evaluate its clinical usage. Reproducibility and analysis speed are important factors to take into account when analyzing drug concentration in body fluids. In this work, we fabricated a droplet-based microfluidic chip for detecting 6-thioguanine in human serum by using the surface-enhanced Raman scattering (SERS) technique. The easily-prepared Au nanoparticles were used as SERS substrates, and reagent mixing and signal acquiring happened in droplets one by one. This assay device is endowed with the superiority in improving determination repeatability with coefficient of variation of no more than 5% (n = 25) and high speed of 10 s each assay. The SERS peak at 1295 cm −1 originated from N1-C6 stretching vibration mode of purine ring was selected for quantitating 6-thioguanine. The signals indicated a satisfied linear relationship with the concentrations of 6-thioguanine in the range of 0.010 μM to 10 μM, with a detection limit of 0.032 μM. The droplet-based microfluidic SERS system was successfully applied for credible and rapid analysis of 6-thioguanine in human serum, and is pretty promising for performing the therapeutic drug monitoring.

CAS / MDL: 70-18-8 154-42-7
研究领域: 分析化学 · 药理学 · 临床医学
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INTERNATIONAL BIODETERIORATION & BIODEGRADATION · 2015 · IF 2.131

Efficient metabolism of the azo dye methyl orange by Aeromonas sp. strain DH-6: Characteristics and partial mechanism

Lin-Na Du,Gang Li,Yu-Hua Zhao,He-Kun Xu,Yang Wang,Ying Zhou,Liang Wang

We investigated biodegradation of the azo dye methyl orange (MO) by Aeromonas sp. DH-6. Nearly 100% decolorization of MO (100 mg l −1 ) by the strain was observed at pH 3.0–7.0 and a broad temperature range (5–45 °C) after incubation for 12 h. Most of the tested carbon and nitrogen sources could significantly enhance MO decolorization, but of the metal ions , only Mg 2+ , Mn 2+ , and 1.5 mM of Ca 2+ could increase the decolorization. The strain still showed a high capacity for decolorizing MO even at a concentration of up to 1000 mg l −1 . Based on the gas chromatography-mass spectrometry analysis (GC-MS) and high performance liquid chromatography analysis (HPLC) data, N,N-dimethyl- p -phenylenediamine and 4-aminobenzenesulfonic acid were identified as the main intermediates of MO biodegradation, and a possible degradation pathway was proposed. Moreover, results of enzyme analysis indicated that laccase, NADH-DCIP reductase, and azo reductase were responsible for the degradation. Overall, high biodegradation efficiency at a broad range of temperatures and dye concentrations suggested that strain DH-6 would have high potential in the bioremediation of azo dyes.

CAS / MDL: 121-57-3 99-98-9
研究领域: 环境科学 · 微生物学 · 染料降解
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CHEMISTRY & BIODIVERSITY · 2025 · IF 2.5

High-resolution Performance of Leaning Pillar[6]arene Functionalized with Imidazolium Ionic Liquids for Gas Chromatography

Yuanyuan Zhang,Haixin Liu,Xiang Xu,Xin Shen,Haolong Qi,Yilin Xing,Mengyi You,Tao Sun,Zhiqiang Cai,Xiaoyan Zhang

Leaning pillar[6]arene (LP6A) is an expanded version of pillar[6]arene (P6A), possessing not only the nanometer-sized cavity of P6A but also a unique desymmetrized leaning tower-like structure, which offers better structural flexibility and cavity adaptability. Here we report the first example of the utilization of imidazolium ionic liquid (IMIL) functionalized LP6A (LP6A-C10-IM-C8[NTf 2 ]) as a stationary phase in capillary gas chromatography (GC). The LP6A-C10-IM-C8[NTf 2 ] capillary column was prepared by the static coating method, showing medium polarity (average polarity 155) and high column efficiency (3758 plates/m). Using long alkyl chains modified LP6A (LP6A-C10) as a reference column, its retention behaviour and resolving performance were elucidated by a mixture of 30 analytes. Importantly, the LP6A-C10-IM-C8[NTf 2 ] column exhibited advantageous separation performance for the challenging isomers of halogenated benzenes, benzaldehydes, phenols, and anilines over the LP6A-C10 and commercial HP-5, HP-35, and DB-17 columns. In addition, the LP6A-C10-IM-C8[NTf 2 ] column has been used to determine the purity of isomer impurities in actual samples, demonstrating good potential in GC separations. Graphical This work reported the first example of utilization of imidazolium ionic liquid (IMIL) functionalized leaning pillar[6]arene (LP6A-C10-IM-C8[NTf 2 ]) as a stationary phase in capillary gas chromatography separations and obtained a high resolution performance for multiple anayltes.

研究领域: 分析化学 · 分离科学 · 材料科学 · 气相色谱
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Surfaces and Interfaces · 2025 · IF 6.3

Cucurbit[6]uril-regulated polyamide thin-film composite membranes for organic solvent nanofiltration

Fuzhi Li,Jian Zhang,Bo Yu,Jianqiang Meng

The simultaneous optimization of permeability and selectivity remains a cardinal challenge in advancing organic solvent nanofiltration (OSN). However, conventional OSN membranes are fundamentally constrained by the “trade-off” problem between permeability and selectivity. To break this limitation, we successfully prepared polyamide thin-film composite (PA-TFC) OSN membranes with both high permeability and high selectivity by incorporating cucurbit[6]uril (CB[6]) into the PA layer. The water insolubility of CB[6] was addressed through complexation with polyethyleneimine (PEI). The successful complexation of CB[6] was verified using techniques such as Ultraviolet-visible spectrophotometer (UV–Vis), Field emission scanning electron microscope (FE-SEM), and other testing approaches. The impact of CB[6] on the chemical composition and surface morphology of the PA layer was also systematically analyzed. In addition, we investigated the effects of monomer concentration on the membrane of permeability-selectivity performance. Experimental results show that the modified membrane, by building the solvent transport channels, showed significantly enhanced methanol permeability (increased by 164 %, 3.19 vs 1.21 L·m -2 ·h -1 ·bar -1 ), while preserving the satisfactory rejection capacity for small molecules (390 Da) (>90 %). Based on the physical parameters of different solvents, we further analyzed the solvent transport mechanism of the prepared OSN membrane. This study provides new insights and approaches for the design of high performance nanofiltration membranes with the aid of macrocycles.

研究领域: 膜科学 · 纳滤 · 材料科学 · 化学工程 · 分离技术
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CHEMISTRY-A EUROPEAN JOURNAL · 2024 · IF 3.9

Narrowband Blue Circularly Polarized Luminescence Emitter Based on BN-Doped Benzo[6]helicene with Stimuli-Responsive Properties

Meiyan Liu,Chenglong Li,Guanming Liao,Fenggui Zhao,Chunxia Yao,Nan Wang,Xiaodong Yin

Graphical Two 1,4-azaborinine [6]helicenes, H[6]BN1 and H[6]BN2 , exhibit blue fluorescence with narrow FWHMs below 31 nm and high PLQY up to 92 %. Desirable circularly polarized luminescence with g lum reaching 4~5×10 −4 and good configurational stability are relized for H[6]BN1 and H[6]BN2 . Mechanochromism occurs between H[6]BN1 ′s crystalline and amorphous states by modulationg π-π intermolecular interanctions. An turquoise OLED based H[6]BN1 is manufactured with the external quantum efficiency (EQE) of 3.18 %. Boron-doped helicenes, known for their unique electronic and photophysical properties, are of great interest for numerous applications. This research introduces two new azabora[6]helicenes, H[6]BN1 and H[6]BN2 , synthesized through an efficient method. These molecules have boron and nitrogen atoms in opposing positions, enhancing their distinctive attributes. Both helicenes show excellent emission properties, with H[6]BN1 and H[6]BN2 exhibiting narrowband blue fluorescence and circularly polarized luminescence (CPL), achieving g lum values of 4~5×10 −4 which is beneficial for chiroptical applications. The addition of a donor group, 3, 6-di-tert-butyl-9H-carbazole, in H[6]BN2 improves luminescence, likely due to enhanced molecular orbital overlap and electron delocalization. H[6]BN1 ′s needle-like single crystals exhibit mechanochromism, changing luminescent color from yellow to green under mechanical stress, which is promising for stimulus-responsive materials. In conclusion, this study presents a novel class of BN[6]helicenes with superior chiroptical properties. Their combination of electronic features and mechanochromism makes them ideal for advanced chiroptical materials, expanding the potential of helicene-based compounds and offering new directions for the synthesis of molecules with specific chiroptical characteristics.

研究领域: 有机光电材料 · 光学材料科学
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Heliyon · 2024 · IF 3.4

A sensitive and specific LC–MS/MS method for determination of a novel antihypertensive peptide FR-6 in rat plasma and pharmacokinetic study

Yu Yang,Xingyan Bao,Jiangyue Ning,Ruiyan Huang,Yuan Liang,Zelong Yan,Haotian Chen,Li Ding,Chang Shu

The investigation of peptide drugs has become essential in the development of innovative medications for hypertension. In this study, a sensitive high-performance liquid chromatography tandem mass spectrometry (HPLC-MS/MS) method was developed to determine the plasma concentration and stability of the antihypertensive peptide FR-6 in rats. An isotopically labeled peptide (with an unchanged sequence) was utilized as an internal standard (IS) for validation purposes. Subsequently, this assay was employed to examine the pharmacokinetics of different administration methods (tail vein and gavage) in Sprague Dawley (SD) rats. Extracted plasma samples underwent sample preparation through methanol protein precipitation, followed by elution of FR-6 on Wondasil C18 Superb column (4.6 × 150 mm, 5 μm), using a mobile phase consisting of formic acid (0.1%) in water (A) and formic acid (0.125%)-ammonium formate (2 mM) in methanol (B). Ion pairs corresponding to FR-6 and IS were monitored via multiple reaction monitoring (MRM) under positive ion mode: m / z 400.7 → 285.1 for FR-6 and m / z 406.1 → 295.1 for IS detection respectively. The method exhibited excellent linearity with respect to FR-6 concentrations. In addition, the inter-day and intra-day precision were 0.61–6.85% and 1.76–11.75%; the inter-day and intra-day accuracy were −7.28–0.13% and −7.20–2.28%, respectively. In conclusion, the matrix effect, extraction recovery, and stability data were validated according to FDA recommended acceptance criteria for bioanalytical methods. This validated method serves as a reliable tool for determining the concentration of antihypertensive peptide FR-6, and has been successfully applied in pharmacokinetic studies involving rats.

CAS / MDL: 64-18-6 9041-08-1
研究领域: 药理学 · 分析化学
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Analytical Methods · 2018 ·Vol. 11 ·期 2 ·157-162 · IF 2.073

Electrochemical determination of PIK3CA gene associated with breast cancer based on molybdenum disulfide nanosheet-supported poly(indole-6-carboxylic acid)

Jimin Yang,Xuesong Yin,Wei Zhang

In our study, we report the development of molybdenum disulfide (MoS2) nanosheet-supported poly(indole-6-carboxylic acid) (PIn6COOH) and its usage for the electrochemical determination of circulating tumor DNA (ctDNA) such as PIK3CA gene associated with breast cancer. The MoS2 nanosheets prepared by the solvent exfoliation method from commercial bulk MoS2 were first immobilized on the surface of a carbon paste electrode; then, PIn6COOH, a novel electroactive material, was electropolymerized on the MoS2 substrate by the potentiostatic method to form a unique nanocomposite structure. The physical adsorption between aromatic In6COOH monomers and MoS2 efficiently improved the electropolymerization efficiency, resulting in increased electrochemical response of PIn6COOH. Owing to the presence of abundant carboxyl groups, probe ssDNA was covalently immobilized on the carboxyl-terminated PIn6COOH/MoS2 nanocomposite through free amines of DNA sequences based on 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide and N-hydrosulfosuccinimide crosslinking reaction. The covalently immobilized probe ssDNA could selectively hybridize with its target DNA to form dsDNA on the surface of the PIn6COOH/MoS2 nanocomposite. The self-signal changes of PIn6COOH induced by DNA immobilization and hybridization could be sensitively recognized via cyclic voltammetry and electrochemical impedance spectroscopy. This developed biosensor showed high performance of DNA hybridization with a detection limit of 1.5 × 10−17 mol L−1 for the detection of PIK3CA gene. The easy construction of this biosensor besides its fine sensitivity and very low time consumption can make this PIn6COOH/MoS2 nanocomposite very highly competitive for further applications in carcinoma diagnostic and therapeutic fields.

研究领域: 生物医学工程 · 分子诊断学 · 癌症研究
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ADSORPTION-JOURNAL OF THE INTERNATIONAL ADSORPTION SOCIETY · 2024 · IF 3

18-Crown-6-ether assembly of cesium ion-imprinted polymer enabling efficiently selective separation of cs(I) from aqueous solution

Ma Licheng,Qi Jungang,Gao Leqi,Wei Tao,Guo Yanhua

In this study, a cesium ion imprinted polymer (Cs(I)-IIP) was prepared by free radical thermal polymerization using 18-crown-6-ether (18C6) as ligand, methacrylic acid (MAA) as functional monomer, and ethylene glycol dimethacrylate (EGDMA) as crosslinking agent, which can be used for adsorption and separation of cesium ions from low-concentration solutions. The adsorption kinetic and isotherm results showed that the adsorption of Cs + fitted to the pseudo-second-order kinetic model and Langmuir model, indicating that the adsorption of Cs + on Cs(I)-IIP was the monolayer chemical adsorption. The maximum adsorption capacity was 84.21 mg·g − 1 . The selective adsorption properties are performed in Cs + , Li + , Na + , and K + multicomponent systems. The results showed that the Cs(I)-IIP has a high selectivity in the presence of coexisting Li + , Na + , and K + , and the selectivity coefficients ( K’ ) of Cs(I)-IIP for Cs + /Li + , Cs + /Na + , Cs + /K + are 2.1, 1.56, and 1.33, respectively. The high adsorption capacity and selectivity are attributed to the introduction of imprinting technology to form specific Cs + recognition adsorption sites, and the 18C6 cavity was easier to recognize Cs + in the competitive adsorption process. Finally, the Cs(I)-IIP can be regenerated and reused for 10 times with the adsorption capacity only decreased by 8.1%, indicating that the polymer has good reuse performance.

研究领域: 材料科学 · 环境科学
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