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tryptophan
Microbiology Spectrum · 2024 · IF 3.7

Interplay between gut microbiota and tryptophan metabolism in type 2 diabetic mice treated with metformin

Yvhao Xie,Xinxin Li,Qingshi Meng,Jinjun Li,Xin Wang,Liying Zhu,Weiwei Wang,Xiaoqiong Li

Tryptophan (TRP) metabolites have been identified as potent biomarkers for complications of type 2 diabetes mellitus (T2DM). However, it remains unclear whether the therapeutic effect of metformin in T2DM is related to the modulation of TRP metabolic pathway. This study aims to investigate whether metformin affects TRP metabolism in T2DM mice through the gut microbiota. A liquid chromatography-tandem mass spectrometry method was established to determine 16 TRP metabolites in the serum, colon content, urine, and feces of T2DM mice, and the correlations between metabolites and the T2DM mice gut microbiota were performed. The method demonstrated acceptable linearity (R2 > 0.996), with the limit of quantification ranging from 0.29 to 69.444 nmol/L for 16 analytes, and the limit of detection ranging from 0.087 to 20.833 nmol/L. In T2DM mice, metformin treatment effectively restored levels of indole-3-lactic acid (ILA), indole-3-propionic acid (IPA), and the ILA/IPA ratio, along with several aryl hydrocarbon receptor ligands in the serum, with a notable impact in the colon but not in the urine. This restoration was accompanied by a shift in the relative abundance of Dubosiella, Turicibacter, RF39, Clostridia_UCG-014, and Alistipes. Spearman’s correlation analysis revealed positive correlations between Turicibacter and Alistipes with IPA and indole-3-acetic acid. Conversely, these genera displayed negative correlations with ILA and kynurenine. In addition, our study revealed the presence of endogenous indole pathway in germ-free mice, and the impact of metformin on endogenous TRP metabolism in T2DM mice cannot be disregarded. Further research is needed to investigate the regulation of TRP metabolism by metformin.

研究领域: 药理学 · 微生物学 · 代谢组学 · 糖尿病研究 · 分子生物学
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TALANTA · 2018 · IF 4.244

A highly efficient chiral sensing platform for tryptophan isomers based on a coordination self-assembly

Peng Lei,Ying Zhou,Guomei Zhang,Yan Zhang,Caihong Zhang,Shasha Hong,Yajuan Yang,Chuan Dong,Shaomin Shuang

Construction of convenient and effective method for enantiomer identification is of vital significance for biochemistry and medical science. Herein, we design an effective sensor for chiral recognition of tryptophan (Trp) enantiomers, and self-assembly of Cu 2+ -modified β-cyclodextrin on poly- L -arginine/multi-walled carbon nanotubes (Cu-β-CD/PLA/MWCNTs) is studied. Meanwhile, Cu 2+ acts as a cap to prevent the release of the high energy water and compel Trp enantiomer into the smaller opening of β-cyclodextrin. Recognition of L -Trp is accomplished by the formation of hydrogen bonds between the amino of L -Trp and the high energy water confined in cavity of Cu-β-CD. Compared with D -Trp, the sensor exhibits favorable chiral recognition toward L -Trp with a separation coefficient of 3.37. And the chiral sensor presents admirable enantiomers determination with excellent sensitivity, providing a good linear correlation in the range of 1 × 10 −6 M~5.5 × 10 −5 M, and the detection limit can reach 3.3 × 10 −7 M (S/N = 3). Besides, the proposed sensor has been able to predict the percentage of D -Trp in the racemic mixture, suggesting its potential applications in the enantiomer recognition field.

研究领域: 生物化学 · 医学科学 · 分析化学
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ANALYST · 2024 ·Vol. 149 ·期 6 ·1753-1758 · IF 3.6

A chiral metal–organic framework/cyclodextrin sensing interface for the chiral discrimination of tryptophan enantiomers

Haowei Huang,Junyao Li,Wenrong Cai,Datong Wu,Laidi Xu,Yong Kong

A chiral metal–organic framework (CMOF) was synthesized by introducing L-histidine (L-His) to zeolitic imidazolate framework-8 (ZIF-8) and then grafting with carboxymethyl-β-cyclodextrin (CM-β-CD). Compared with L-His-ZIF-8, the CM-β-CD-functionalized L-His-ZIF-8 (L-His-ZIF-8-CD) showed significantly enhanced discrimination ability for the tryptophan (Trp) enantiomers owing to the inherent chirality of CM-β-CD. The specificity of the chiral interface was also studied, and the results indicated that the discrimination ability for Trp enantiomers is significantly stronger than that for the enantiomers of cysteine (Cys) and tyrosine (Tyr), which might be due to the better matching between the indole ring of Trp and the chiral cavity of CM-β-CD.

研究领域: 化学 · 分析化学 · 材料科学
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RSC Advances · 2015 ·Vol. 5 ·期 114 ·93850-93857 · IF 3.84

Enantiomer separation of propranolol and tryptophan using bovine serum albumin functionalized silica nanoparticles as adsorbents

Wei Li,Guo-Sheng Ding,An-Na Tang

The immobilization of popular chiral selectors on the surface of nanomaterials to prepare new chiral adsorbents for preparative chiral separation is a research hotspot in separation science nowadays. In this study, bovine serum albumin (BSA) modified silica nanoparticles were prepared by using polydopamine (PDA) as a versatile multifunctional secondary reaction platform. The preparation method was facile, cost-effective and environmentally friendly. The new chiral adsorbents were then investigated for the separation of representative chiral drug enantiomers. For propranolol and tryptophan, the multi-step adsorption enhanced the chiral performance to a great degree. On increasing the starting percent enantiomeric excess (%, e.e.) of the enantiomeric mixtures, the %, e.e. value of the resulting solution increased to almost 100% under the same operating conditions. For simplicity and rapidness, the results of adsorption were measured by capillary electrophoresis (CE) using carboxymethyl-β-cyclodextrin (CM-β-CD) or α-cyclodextrin (α-CD) as additives into the background electrolyte solution. The experimental results also showed that the thus-prepared nanomaterials could be readily recycled at least three times, demonstrating their great stability and possibility in practical use.

CAS / MDL: 10016-20-3
研究领域: 分离科学 · 纳米技术 · 药物化学 · 分析化学
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MICROCHIMICA ACTA · 2014 ·Vol. 181 ·期 11 ·1407-1413 · IF 3.719

Colorimetric chiral discrimination and determination of enantiometric excess of D/L-tryptophan using silver nanoparticles

Liu Cunwei,Li Baoxin,Xu Chunli

We report on a method for visual differentiation between the D- and L-forms of tryptophan (Trp). It is based on the inherent chirality of citrate-capped silver nanoparticles (AgNPs; ca. 15 nm in diameter) that can be used as chiral selector for D- and L-forms of Trp. On addition of D-Trp to a solution of the AgNPs, a color change from yellow to red can be seen, while no color change is found on addition of L-Trp. The chiral assay can be used to determine the enantiometric excess of D-Trp in the range from −50 % to 100 %. The effect can be detected with bare eyes and quantified by spectrophotometry. Notably, this method does not require any labeling or chiral modification. The method excels by its sensitivity, low cost, good availability of materials, and its simplicity. The silver nanoparticles can discriminate the absolute configuration of Trp and determine the enantiomeric excess of Trp

研究领域: 分析化学 · 纳米技术 · 生物化学
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SENSORS AND ACTUATORS B-CHEMICAL · 2015 · IF 4.097

Simultaneous determination of ascorbic acid, uric acid, tryptophan and adenine using carbon-supported NiCoO2 nanoparticles

Fengchun Yang,Qianjie Xie,Hanzhi Zhang,Sha Yu,Xin Zhang,Yehua Shen

The electrochemical sensor based on carbon-supported NiCoO 2 nanoparticles (NiCoO 2 /C) modified glassy carbon electrode (GCE) was constructed to simultaneously determine small biomolecules such as ascorbic acid (AA), uric acid (UA), tryptophan (Trp) and adenine. The morphology and structure of NiCoO 2 nanoparticles (NPs) were characterized by scanning electron microscopy, transmission electron microscopy, X-ray diffractometry and Fourier transform infrared spectroscopy. Electrochemical studies of simultaneous detection were carried out by differential pulse voltammetry (DPV). The combination of Ni and Co oxides endowed the NiCoO 2 /C modified GCE with electrocatalytic activity, sensitivity, and selectivity with well-separated oxidation peaks toward AA, UA, Trp and adenine. Two linear calibrations for AA, UA, Trp and adenine were obtained over ranges of 5.0   ×   10 −5 –485.4   ×   10 −6 and 485.4   ×   10 −6 –943.4   ×   10 −6   M with detection limit (S/N   =   3) of 3.3   ×   10 −6 , 5.3   ×   10 −6 , 5.7   ×   10 −6 and 3.9   ×   10 −6   M respectively. In addition, the modified electrode was successfully applied for the simultaneous determination of AA, UA, Trp, and adenine in many real samples with reliable recovery.

研究领域: 分析化学 · 生物医学工程
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Analytical Methods · 2016 ·Vol. 8 ·期 17 ·3481-3487 · IF 1.915

Efficient bienzyme nanocomposite film for chiral recognition of L-tryptophan, L-phenylalanine and L-tyrosine

Lili Wang,Wencheng Gong,Fang Wang,Zhenya Yu,Zilin Chen

An efficient bienzyme nanocomposite film-based biosensor for L-amino acid recognition has been developed and characterized. The biosensor was fabricated by immobilizing horseradish peroxidase (HRP) and L-amino acid oxidase (L-AAODx) in poly(toluidine blue) film (polyTB) at the surface of a multi-walled carbon nanotube (CNTs) modified glassy carbon electrode (GCE). Only L-amino acids can be electrochemically oxidized by L-AAODx in the presence of oxygen (O2) to produce hydrogen peroxide (H2O2), which can be further reduced to H2O by HRP at a low potential of −0.1 V. The concentration of L-amino acids was estimated by the reduction current of H2O2. The polyTB film, acting as the enzyme-immobilization carrier and redox mediator, accelerated electron transfer between analytes and the electrode. At the same time, CNTs with excellent conductivity and strong adsorption ability enhanced the utilization of the enzymes. The performance of this biosensor was evaluated by electrochemical techniques and it showed high selectivity and fast response for the chiral recognition of L-amino acids, including L-tryptophan (L-Trp), L-phenylalanine (L-Phe) and L-tyrosine (L-Tyr). The low potential reduced the interference of some coexisting biomolecules for the determination of the L-amino acids. The recovery of the three amino acids in milk indicated the feasibility of this biosensor for use in complex samples.

研究领域: 生物化学 · 分析化学
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ELECTROANALYSIS · 2015 ·Vol. 28 ·期 4 ·868-873 · IF 2.138

Chiral Recognition of Tryptophan Enantiomers Based on β-Cyclodextrin-platinum Nanoparticles/Graphene Nanohybrids Modified Electrode

Juanjuan Xu,Qinghong Wang,Chunzhi Xuan,Qiao Xia,Xia Lin,Yingzi Fu

The nanohybrids which based on β-cyclodextrin, platinum nanoparticles and graphene (β-CD-PtNPs/GNs) were successfully synthesized and characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), fourier transform infrared spectroscopy (FT-IR) and electrochemical impedance spectroscopy (EIS). Then they were used to construct a simple and reliable chiral sensing platform to interact with tryptophan (Trp) enantiomers. Differential pulse voltammetry (DPV) was used to investigate the stereo selectivity of β-CD-PtNPs/GNs to Trp enantiomers. After interaction, the obvious difference of peak currents of L -Trp and D -Trp was obtained, indicating this strategy could be employed to chiral recognition of Trp enantiomers. Under the optimum conditions, the chiral sensor exhibited a good linear response to Trp enantiomers in a linear range of 5.0×10 −5 to 5.0×10 −3 M with a low limit of detection of 1.7×10 −5 M (S/N=3). This approach provided a new available platform to recognize and determine Trp enantiomers.

CAS / MDL: 16941-12-1 111689-03-3
研究领域: 分析化学 · 生物传感 · 电化学
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ELECTROCHEMISTRY COMMUNICATIONS · 2016 · IF 4.569

Potato starch as a highly enantioselective system for temperature-dependent electrochemical recognition of tryptophan isomers

Liping Bao,Yongxin Tao,Xiaogang Gu,Baozhu Yang,Linhong Deng,Yong Kong

A simple but highly enantioselective system based on potato starch (PS) modified electrode was developed for electrochemical recognition of tryptophan (Trp) isomers. Due to favorability of host–guest interactions between PS and D-Trp, PS preferably combined with D-Trp compared with L-Trp, resulting in larger amount of L-Trp penetrating through the left-handed double helices of PS to the electrode surface than D-Trp. And therefore, successful recognition of Trp isomers was achieved at the PS-based electrode. The PS-based chiral recognition was temperature dependent, which was attributed to the significant influence of temperature on the H-bonds between PS and the guest molecules. The recognition efficiency was remarkably decreased after hydroxypropyl groups were introduced to PS, and the decreased recognition efficiency at the hydroxypropyl PS (H-PS) might be due to the extra steric hindrance .

CAS / MDL: 9005-25-8
研究领域: 生物化学 · 分析化学
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Microbiome · 2023 ·Vol. 11 ·期 1 ·1-20 · IF 15.5

High-fat diet-disturbed gut microbiota-colonocyte interactions contribute to dysregulating peripheral tryptophan-kynurenine metabolism

Sun Penghao,Wang Mengli,Liu Yong-Xin,Li Luqi,Chai Xuejun,Zheng Wei,Chen Shulin,Zhu Xiaoyan,Zhao Shanting

Background Aberrant tryptophan (Trp)-kynurenine (Kyn) metabolism has been implicated in the pathogenesis of human disease. In particular, populations with long-term western-style diets are characterized by an excess of Kyn in the plasma. Host-gut microbiota interactions are dominated by diet and are essential for maintaining host metabolic homeostasis. However, the role of western diet-disturbed gut microbiota-colonocyte interactions in Trp metabolism remains to be elucidated. Results Here, 4-week-old mice were fed with a high-fat diet (HFD), representing a typical western diet, for 4 weeks, and multi-omics approaches were adopted to determine the mechanism by which HFD disrupted gut microbiota-colonocyte interplay causing serum Trp-Kyn metabolism dysfunction. Our results showed that colonocyte-microbiota interactions dominated the peripheral Kyn pathway in HFD mice. Mechanistically, persistent HFD-impaired mitochondrial bioenergetics increased colonic epithelial oxygenation and caused metabolic reprogramming in colonites to support the expansion of Proteobacteria in the colon lumen. Phylum Proteobacteria -derived lipopolysaccharide (LPS) stimulated colonic immune responses to upregulate the indoleamine 2,3-dioxygenase 1 (IDO1)-mediated Kyn pathway, leading to Trp depletion and Kyn accumulation in the circulation, which was further confirmed by transplantation of Escherichia coli ( E.coli ) indicator strains and colonic IDO1 depletion. Butyrate supplementation promoted mitochondrial functions in colonocytes to remodel the gut microbiota in HFD mice, consequently ameliorating serum Kyn accumulation. Conclusions Our results highlighted that HFD disrupted the peripheral Kyn pathway in a gut microbiota-dependent manner and that the continuous homeostasis of gut bacteria-colonocytes interplay played a central role in the regulation of host peripheral Trp metabolism. Meanwhile, this study provided new insights into therapies against western diet-related metabolic disorders. Video Abstract

CAS / MDL: 22978-25-2 156-54-7
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PHYSICAL CHEMISTRY CHEMICAL PHYSICS · 2023 ·Vol. 25 ·期 10 ·7239-7250 · IF 3.3

Ultrafast Förster resonance energy transfer from tyrosine to tryptophan in monellin: potential intrinsic spectroscopic ruler

Haoyang Li,Simin Cao,Sanjun Zhang,Jinquan Chen,Jianhua Xu,Jay R. Knutson

Ultrafast Förster Resonance Energy Transfer (FRET) between tyrosine (Tyr) and tryptophan (Trp) residues in the protein monellin has been investigated using picosecond and femtosecond time-resolved fluorescence spectroscopy. Decay associated spectra (DAS) and time-resolved emission spectra (TRES) taken with the different excitation wavelengths of 275, 290 and 295 nm were constructed via global analysis. At two of those three excitation loci (275 and 290 nm), earmarks of energy transfer from Tyr to Trp in monellin are seen, and particularly when the excitation is 275 nm, the energy transfer between Tyr and Trp clearly changes the signature emission DAS shape to that indicating excited state reaction (especially on the red side of fluorescence emission, near 380 nm). Those FRET signatures may overlap with the conventional signatory DAS in heterogeneous systems. When overlap and addition occur between FRET type DAS and “full positive” QSSQ (quasi-static self-quenching), mixed DAS shapes will emerge that still show “positive blue side and negative red sides”, just with zero crossing shifted. In addition, excitation decay associated spectra (EDAS) taken with the different emission wavelengths of 330, 350 and 370 nm were constructed. In the study of protein dynamics, ultrafast FRET between Tyr and Trp could provide a basis for an intrinsic (non-perturbing) “spectroscopic ruler”, potentially a powerful tool to detect even slight changes in protein structures.

CAS / MDL: 7558-79-4 7558-80-7
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DIAMOND AND RELATED MATERIALS · 2023 · IF 4.1

2D/2D porous Co3O4/rGO nanosheets act as an electrochemical sensor for voltammetric tryptophan detection

Shiqi Zhang,Peidong Ling,Yi Chen,Jun Liu,Chun Yang

Herein, 2D/2D porous Co 3 O 4 nanosheets/rGO composites modified GCE (Co 3 O 4 /rGO/GCE) were proposed for electrochemical detection of tryptophan (Trp). The surface morphology and structure of Co 3 O 4 /rGO nanosheets were carried out using SEM, XRD , and Raman spectra . Electrochemical performance of Trp on as-synthesized modified electrodes were discussed by CV and EIS techniques. Moreover, the best electrochemical property was also investigated by varying test condition detailedly. Consequently, oxidation peak intensity and current density were 130.3 μA and 336.7 μA·cm −2 on Co 3 O 4 /rGO/GCE at working potential of 0.78 V ( vs. SCE electrode), respectively. They were more than 23-times greater than these on bare GCE in electrochemical detection of Trp. It was attributed to the synergy effect of 2D porous Co 3 O 4 nanosheets (high catalytic activity) and 2D rGO nanosheets (large electrochemical active area). After the optimization, wide linear determination ranges (from 1.0 to 800 μM) and low LOD of 0.26 μM (S/N = 3) were acquired. In addition, these electrodes were further successfully applied to the determination of Trp in commercial amino acid injection samples. This 2D porous Co 3 O 4 /rGO modified GCE sensor could provide a slight view on the design of 2D/2D composite materials with high electrochemical properties.

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