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tryptophan
Journal of Inorganic and Organometallic Polymers and Materials · 2013 ·Vol. 23 ·期 6 ·1492-1500 · IF 1.174

Synthesis, Crystal Structure, Fluorescence and Thermostability of Ni(II), Zn(II), Cd(II) Complexes with Schiff Base 2-Acetylpyridine-d-tryptophan

Zhang Nan,Fan Yu-Hua,Bi Cai-Feng,Zhang Xia,Zhang Peng-Fei,Zhang Zhong-Yu,Li Xin

Three novel transition metal coordination polymers, [Ni(C 18 H 16 N 3 O 2 ) 2 ·2CH 3 OH] n ( 1 ), [Zn(C 18 H 16 N 3 O 2 ) 2 ·4CH 3 OH] n ( 2 ) and [Cd(C 18 H 16 N 3 O 2 ) 2 ·2CH 3 OH] n ( 3 ) (C 18 H 16 N 3 O 2 =2-acetylpyridine- d -tryptophan) were synthesized and characterized by elemental analysis, IR, UV, 1 H NMR and X-ray diffraction single crystal analysis. The analyses of the structures indicate that all three materials crystallize in the tetragonal crystal system, space group P 4 1 2 1 2. They have similar structures; i.e., the Schiff base coordinates in its deprotonated form and behaves as a hexadentate (4N+2O) coordinated ligand to form a distorted octahedron geometry. On the other hand, as a result of the alternate arrangement of chains through N–H···O intermolecular hydrogen bonds interactions, 2-D layers are formed for the three complexes. Furthermore, the luminescent properties and thermal stabilities of the three complexes were investigated.

研究领域: 无机化学 · 配位化学 · 材料化学 · 晶体工程 · 光物理化学
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Current Pharmaceutical Analysis · 2023 ·Vol. 19 ·期 5 ·432-440 · IF 0.6

Experimental and Theoretical Study of Biosurfactants Functionalized Gold Nanoparticles for Mixture Detection and Chiral Recognition of Tryptophan by UV-VIS Spectroscopy

Xiangzong Wu,Yanxia Li,Yiting Chen,Zhenli Qiu,Lu Huang

Background: Tryptophan (Trp) is an essential amino acid and plays important roles in biological processes. The detection of Trp is very important for its biological and chemical study. Moreover, Trp is a chiral compound; due to its importance in biological processes, researchers have been long committed to the chiral recognition and sensing of Trp enantiomers. Methods: Two biosurfactants, sodium cholate and sodium deoxycholate, were used for the preparation of functionalized gold nanoparticles (AuNPs) which were characterized by transmission electron microscope and potentiometer. UV-Vis spectra of functionalized gold nanoparticle solutions with different concentrations of Trp, tyrosine, phenylalanine, D-Trp, and L-Trp were analyzed. Then, the discrimination mechanism was further investigated, and the promotion mechanism of biosurfactants was studied by density functional theory (DFT). Results: Trp could induce the aggregation of unmodified AuNPs in 2 h, while phenylalanine and tyrosine could not. Adding biosurfactants promoted the aggregation process, and D- Trp rather than LTrp was found to be responsible for the aggregation. Therefore, there were interaction differences not only between Trp, phenylalanine, and tyrosine but also between Trp enantiomers. Conclusion: UV-vis spectroscopy could be applied for the direct detection of Trp in mixtures as well as the chiral recognition of Trp enantiomers. DFT calculations proved that the interactions of D-Trp with biosurfactants were the strongest, which contributes to the promotion of aggregation.

研究领域: 分析化学 · 纳米技术 · 生物化学 · 材料科学 · 物理化学
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Journal of Environmental Sciences · 2023 · IF 6.9

Pre-mating nitenpyram exposure in male mice leads to depression-like behavior in offspring by affecting tryptophan metabolism in gut microbiota

Sen Yan,Wei Sun,Sinuo Tian,Zhiyuan Meng,Jinling Diao,Zhiqiang Zhou,Li Li,Wentao Zhu

Several studies have confirmed that the health status of the paternal affects the health of the offspring , however, it remains unknown whether paternal exposure to pesticides affect the offspring health. Here, we used untargeted metabolomics and 16S rRNA sequencing technology, combined with tail suspension test and RT-qPCR to explore the effects of paternal exposure to nitenpyram on the neurotoxicity of offspring. Our results found that the paternal exposure to nitenpyram led to the offspring's depressive-like behaviors, accompanied by the reduction of tryptophan content and the disorder of microbial abundance in the gut of the offspring. Further, we determined the expression of tryptophan metabolism-related genes tryptophanase ( tnaA ) and tryptophan hydroxylase 1 ( TpH1 ) in gut bacteria and colonic tissues. We found that tryptophan is metabolized to indoles rather than being absorbed into colonocytes, which coursed the reduce of tryptophan availability after nitenpyram exposure. In conclusion, our study deepens our understanding of the intergenerational toxic effects of pesticides.

CAS / MDL: 7789-20-0
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Biosensors-Basel · 2023 ·Vol. 13 ·期 12 ·1024 · IF 5.4

C-undecylcalix[4]resorcinarene Langmuir–Blodgett/Porous Reduced Graphene Oxide Composite Film as a Electrochemical Sensor for the Determination of Tryptophan

Yanju Wu,Keyu Chen,Fei Wang

In this study, a composite film was developed for the electrochemical sensing of tryptophan (Trp). Porous reduced graphene oxide (PrGO) was utilized as the electron transfer layer, and a C-undecylcalix[4]resorcinarene Langmuir–Blodgett (CUCR-LB) film served as the molecular recognition layer. Atomic force microscopy (AFM), transmission electron microscopy (TEM), Raman spectroscopy, scanning electron microscopy (SEM), and electrochemical experiments were employed to analyze the characteristics of the CUCR-LB/PrGO composite film. The electrochemical behavior of Trp on the CUCR-LB/PrGO composite film was investigated, revealing a Trp linear response range of 1.0 × 10−7to 3.0 × 10−5mol L−1and a detection limit of 3.0 × 10−8mol L−1. Furthermore, the developed electroanalytical method successfully determined Trp content in an amino acid injection sample. This study not only introduces a rapid and reliable electrochemical method for the determination of Trp but also presents a new strategy for constructing high-performance electrochemical sensing platforms.Keywords:Langmuir–Blodgett film;porous reduced graphene oxide;calix[4]arene;electrochemical sensing;tryptophan

✓ 已验证 产品关联 DOI PubMed 高影响因子
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International Journal of Electrochemical Science · 2023 · IF 1.5

An Electrochemical Sensor Based on MB/Ag-ZnO/Graphene Modified Glassy Carbon Electrode for Determination of L- Tryptophan in Biofluid Samples

Yao Wang,Dan Li,Junfeng Kang,Shiye Guan,Daoxin Wu

In this work, graphene (GR) and Ag-ZnO nanocomposites were prepared and used together with methylene blue (MB) as electrode materials to modify a glassy carbon electrode (GCE). The electrochemical behavior of L-tryptophan (L-Trp) on the fabricated MB/Ag-ZnO/GR/GCE was investigated by cyclic voltammetry and differential pulse voltammetry. MB/Ag-ZnO/GR clearly enhanced the electrochemical oxidation of L-Trp. In a 0.1 mol/L phosphate buffer solution at pH 4.0, the peak current response at the modified electrode increased linearly with an increase in the L-Trp concentration from 2.0 x 10 -6 to 1.4 x 10 -4 mol/L, and the detection limit (S/N = 3) was 1.0 × 10 -6 mol/L. The electrode showed good reproducibility, stability, and selectivity. The sensor was used for the determination of L-Trp in biofluid samples (pig serum and pig urine), and the recovery rate ranged from 97.1% to 104.2%. The fabricated electrode was proposed for the electrochemical analysis of L- Trp, indicating the potential for practical applications in the biological field.

CAS / MDL: 61-73-4
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JOURNAL OF MOLECULAR LIQUIDS · 2020 · IF 5.065

Deep-eutectic solvents simultaneously used as the phase-forming components and chiral selectors for enantioselective liquid-liquid extraction of tryptophan enantiomers

Shaoping Ma,Fenfang Li,Liangliang Liu,Liping Liao,Li Chang,Zhijian Tan

Two-phase system was widely used for the enantioselective liquid-liquid extraction (ELLE) of various enantiomers . The organic solvents are generally used as the extractants, moreover, the additional chiral selectors should be added to the extraction system. In this study, a biphasic recognition chiral extraction (BRCE) system based on hydrophilic and hydrophobic DESs was developed for the ELLE of tryptophan enantiomers. DESs can be simultaneously used as the phase-forming components and chiral selectors. The hydrophobic/hydrophilic methyl trioctyl ammonium chloride- L(+)-Diethyl L-tartrate/HP-β-CD-L-(−)-Malic Acid (MTAC-DE/HC-MA) system was screened as the optimal extraction system. The molar ratios of hydrogen-bond acceptor (HBA) and hydrogen-bond donor (HBD) in DESs were optimized for the enantioseparation. The other factors of phase volume ratio, initial tryptophan concentration, pH value, and extraction temperature were studied. The maximum enantiomeric excess ( e.e. ) value of 38.46% was obtained under the optimal conditions by one-step extraction. This BRCE system used for the chiral separation of tryptophan enantiomers has the advantages of environmental friendliness , simple operation, and high efficiency, which has the practical application potentiality in the continuous enantioseparation process.

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ANALYTICA CHIMICA ACTA · 2020 · IF 5.977

Highly sensitive detection of tryptophan (Trp) in serum based on diazo-reaction coupling with Surface-Enhanced Raman Scattering and colorimetric assay

Min Fan,Dechan Lu,Ruiyun You,Cairou Chen,Yudong Lu,Yang Wu,Huiying Shen,Shangyuan Feng

Tryptophan plays an important role in the metabolic pathway and tryptophan metabolism is abnormal in tumor tissues. Therefore, Trp and its metabolites in body fluids can be used as tumor markers for cancer monitoring. However, the traditional tryptophan detection method has many shortcomings, such as low sensitivity, time-consuming and so on, which is difficult to meet the clinical needs. Herein, a rapidly, sensitive and reliable method for indirectly detecting Tryptophan (Trp) in serum was proposed by combining diazo-coupling reaction mechanism with surface-enhanced Raman scattering (SERS). The limit of detection (LOD) of Trp can be as low as 20 nM, which is much lower than existing detection methods. In addition, because of obvious change in color in diazo-coupling reaction, a colorimetric detection was applied for convenient determination of Trp in the concentration ranged from 3 × 10 −5 - 10 −3  M. Furthermore, with the support of good results by SERS assay, the presented method was successfully carried out for the determination of Trp in serum that came from healthy people and colorectal cancer patients. Comparing the difference of Trp content in serum between the two groups, it was found that tryptophan metabolism disorder exists in colorectal cancer patients, which suggested that the accurate detection of tryptophan content may provide important reference for the pathogenesis, prediction and prevention of colorectal cancer.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF CHEMICAL AND ENGINEERING DATA · 2019 · IF 2.298

Measurement of the Thermal Conductivity of 1-Butyl-3-methylimidazolium l-Tryptophan + Water + Ethanol Mixtures at T = (283.15 to 333.15) K

Xing Cui,Hai Zhu,Chao-Hong He,Ke-Jun Wu

The thermal conductivities of 1-butyl-3-methylimidazolium l-tryptophan ([BMIM][l-trp]), water, ethanol, [BMIM][l-trp] + water, [BMIM][l-trp] + ethanol, water + ethanol, and [BMIM][l-trp] + water + ethanol were investigated from 283.15 to 333.15 K covering the whole scale of concentration at atmospheric pressure with the transient hot wire method. The thermal conductivities of pure [BMIM][l-trp] decease linearly from 0.180 to 0.177 W·m–1·K–1 with increasing temperature. The uncertainty of the measurement was less than 2% at the 0.95 confidence level. The experimental data of binary and ternary mixtures were correlated by a second-order Scheffé polynomial as a function of composition and temperature. The average relative deviation of the calculated values with experimental data was 0.58%.

CAS / MDL: 64-17-5
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JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES · 2019 · IF 2.813

Ultra-performance liquid chromatography-tandem mass spectrometry quantitative profiling of tryptophan metabolites in human plasma and its application to clinical study

Yun Chen,Hui Chen,Ganggang Shi,Min Yang,Fuchun Zheng,Zhijie Zheng,Shuyao Zhang,Shilong Zhong

A sensitive, rapid and reliable ultra-performance liquid chromatography-tandem mass spectrometry (UPLC–MS/MS) method was developed and validated to assay tryptophan (TRP) and its nine metabolites, including kynurenine (KYN), kynurenic acid (KYNA), 3-hydroxykynurenine (3-HK), 3-hydroxyanthranilic acid (3-HAA), xanthurenic acid (XA), 5-hydroxytryptamine (5-HT), 5-hydroxyindoleacetic acid (5-HIAA), 3-indolepropionic acid (IPA) and 3-indoleacetic acid (IAA) in human plasma. Tryptophan- d5 (TRP- d5 ) and carbamazepine (CAR) were applied to the method quantification, where TRP- d5 was the corresponding internal standard (IS) for TRP and KYN, and CAR was the corresponding IS for the other analytes. Plasma samples were processed by deproteinisation with acetonitrile , followed by separation on an Acquity UPLC HSS T3 column by using gradient elution with 0.1% ( v / v ) formic acid in water and acetonitrile and detection by electrospray ionisation tandem mass spectrometry in positive ion multiple reaction monitoring (MRM) within a total run time of 5 min. The calibration ranges were 3–600 ng/mL for 3-HK, 1.5–300 ng/mL for 5-HT, 25–5000 ng/mL for KYN, 1–200 ng/mL for XA, 100–20,000 ng/mL for TRP, 5–1000 ng/mL for KYNA, 2–400 ng/mL for 3-HAA, 2.5–500 ng/mL for 5-HIAA and 10–2000 ng/mL for IAA and IPA. All intra- and inter-day analytical variations were acceptable. Matrix effect and recovery evaluation proved that matrix effect can be negligible, and sample preparation approach was effective. The newly developed method can simultaneously determine a panel of TRP metabolites and was successfully applied in the clinical study characterising TRP metabolism in healthy volunteers.

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JOURNAL OF CHEMICAL THERMODYNAMICS · 2018 · IF 2.631

Experimental solubility evaluation and thermodynamic analysis of biologically active D-tryptophan in aqueous mixtures of N,N-dimethylformamide and several alcohols

Xiao Feng,Ali Farajtabar,Hu Lin,Gaoquan Chen,Zhiying Wang,Xinbao Li,Hongkun Zhao

The D-tryptophan solubility in aqueous solutions of methanol, ethanol, isopropanol and N , N -dimethylformamide (DMF) was measured by the saturation shake-flask method at temperatures ranging from 283.15 K to 333.15 K. The maximum solubility was found in water for alcohol (1) + water (2) mixtures, and in neat DMF for DMF (1) + water (2) mixture. When the same temperature and mass fraction of the water is given, the highest mole fraction solubility of D-tryptophan was found in (DMF + water). The solid phases were tested by X-ray powder diffraction (XPRD) showing no polymorphic transformation, solvate formation or crystal   transition. Three solubility models, i.e. the Jouyban-Acree, van’t Hoff-Jouyban-Acree and Apelblat-Jouyban-Acree were employed to correlate the experimental solubility values so as to obtain thermodynamic parameters. The RAD and RMSD data were no more than 1.65% and 9.40 × 10 −5 , respectively. Linear solvation energy relationship analysis based on Kamlet-Taft parameters indicated that the variation of D-tryptophan solubility depended on π ∗ for methanol (ethanol, isopropanol) (1) + water (2), and cavity term for DMF (1) + water (2). The preferential solvation parameters ( δx 1,3 ) for methanol, ethanol, isopropanol and DMF derived by means of the inverse Kirkwood–Buff integrals were negative in the four solvent mixtures with intermediate and alcohol-rich compositions, which indicated that D-tryptophan was preferentially solvated by water. The higher solvation by water could be explained in terms of the higher acidic behaviour of the solvents interacting with the Lewis basic groups of the D-tryptophan. However D-tryptophan is preferentially solvated neither by water nor by DMF in DMF + water mixture.

CAS / MDL: 153-94-6
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2025 · IF 6.2

“Shield” Armed Programmable Probiotics Harboring α-Aminoadipate Aminotransferase Gene Regulate Tryptophan Metabolism and Gut Microbiota to Alleviate the Inflammatory Bowel Disease

Aijiang Liu,Jun Ma,Zengguang Liu,Tianyuan Qiu,Qixuan Zhao,Guangquan Li,Xiao Liang,Quanshun Li

Current treatment of inflammatory bowel disease (IBD) relies on anti-inflammatory and immunosuppressive agents. However, this concept is considered outdated due to its restricted efficacy and unavoidable side effects. Herein, a polynorepinephrine-coated programmable probiotic expressing α-aminoadipate aminotransferase (NE-EcN-pA) was constructed to improve the levels of kynurenic acid and xanthurenic acid in the intestine by modulating the endogenous tryptophan metabolism. The NE layer could protect EcN-pA against the harsh environment of the gastrointestinal tract, enhancing its survival and colonization. In UC mice, oral administration of NE-EcN-pA effectively alleviated intestinal inflammation and restored the intestinal epithelial barrier owing to the activation of the aryl hydrocarbon receptor pathway. Furthermore, NE-EcN-pA promoted the diversity of intestinal flora, improved the imbalance of flora, and enhanced the content of short-chain fatty acids in the colon. Overall, NE-EcN-pA can regulate endogenous tryptophan metabolism and gut microbiota, showing promise in the treatment of gastrointestinal disorders.

CAS / MDL: 89-57-6 9001-75-6
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MedComm · 2024 ·Vol. 5 ·期 5 ·e555 · IF 10.7

Tryptophan deficiency induced by indoleamine 2,3-dioxygenase 1 results in glucose transporter 1-dependent promotion of aerobic glycolysis in pancreatic cancer

Heng Liang,Jiani Zhan,Yunqiu Chen,Zikang Xing,Zhen Ning Tony He,Yuying Liu,Xuewen Li,Yijia Chen,Zhiyao Li,Chunxiang Kuang,Dan Yang,Qing Yang

Indoleamine 2,3-dioxygenase 1 (IDO1), the key enzyme in the catabolism of the essential amino acid tryptophan (Trp) through kynurenine pathway, induces immune tolerance and is considered as a critical immune checkpoint, but its impacts as a metabolism enzyme on glucose and lipid metabolism are overlooked. We aim to clarify the potential role of IDO1 in aerobic glycolysis in pancreatic cancer (PC). Analysis of database revealed the positive correlation in PC between the expressions of IDO1 and genes encoding important glycolytic enzyme hexokinase 2 (HK2) , pyruvate kinase (PK) , lactate dehydrogenase A (LDHA) and glucose transporter 1 (GLUT1) . It was found that IDO1 could modulate glycolysis and glucose uptake in PC cells, Trp deficiency caused by IDO1 overexpression enhanced glucose uptake by stimulating GLUT1 translocation to the plasma membrane of PC cells. Besides, Trp deficiency caused by IDO1 overexpression suppressed the apoptosis of PC cells via promoting glycolysis, which reveals the presence of IDO1–glycolysis–apoptosis axis in PC. IDO1 inhibitors could inhibit glycolysis, promote apoptosis, and exhibit robust therapeutic efficacy when combined with GLUT1 inhibitor in PC mice. Our study reveals the function of IDO1 in the glucose metabolism of PC and provides new insights into the therapeutic strategy for PC.

CAS / MDL: 1799753-84-6
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