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tryptophan
Science Bulletin · 2023 · IF 18.9

Sinomenine ameliorates rheumatoid arthritis by modulating tryptophan metabolism and activating aryl hydrocarbon receptor via gut microbiota regulation

Zheng-Meng Jiang,Su-Ling Zeng,Tian-Qing Huang,Yang Lin,Fang-Fang Wang,Xing-Jiao Gao,Jing Li,Ping Li,E-Hu Liu

Gut microbiota dysbiosis is associated with the development of rheumatoid arthritis (RA). Sinomenine (SIN) is an effective immunosuppressive and anti-inflammatory drug used for treating RA, but how SIN regulates gut microbiota to alleviate RA remains underexplored. To identify the critical gut microbial species and microbial metabolites associated with the RA-protective effects of SIN, the microbiota-dependent anti-RA effects of SIN were assessed by 16S rRNA gene sequencing, antibiotic treatment, and fecal microbiota transplantation. Metabolomics analysis, transcriptional analysis, and targeted bacteria/metabolites gavage were conducted to explore how SIN regulates gut microbiota to reduce the severity of RA. SIN could restore intestinal microbial balance by mainly modulating the abundance of Lactobacillus , and significantly relieve collagen-induced arthritis (CIA) symptoms in a gut microbiota-dependent manner. SIN significantly elevated microbial tryptophan metabolites indole-3-acrylic acid (IA), indole-3-propionic acid (IPA), and indole-3-acetic acid (IAA). Tryptophan metabolites supplementation could activate aryl hydrocarbon receptor (AhR) and regulate Th17/Treg balance in CIA rats. Intriguingly, SIN relieved the arthritis symptoms involving the enrichment of two beneficial anti-CIA Lactobacillus species, L. paracasei and L. casei by mono-colonization. The promising therapeutic function of SIN was mostly attributed to the activation of AhR by explicitly targeting the Lactobacillus and microbial tryptophan metabolites. The intestinal bacterium L. paracasei and L. casei may be used to reduce the severity of CIA.

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Food Bioscience · 2019 · IF 3.22

Pepsin-catalyzed plastein reaction with tryptophan increases the in vitro activity of lactoferrin hydrolysates with BGC-823 cells

Chun-Min Ma,Tie-Jing Li,Xin-Huai Zhao

Lactoferrin hydrolysates (LF-H) were digested using pepsin and modified using a pepsin-catalyzed plastein reaction with tryptophan (Trp) to obtain a target product. LF-H, the target product, plastein reaction-modified LF-H alone, and a mixture of LF-H and Trp were evaluated for their activities with human gastric cancer BGC-823 cells at 24 and 48 h. Assay results indicated that the target product had decreased free amino groups and had incorporated Trp. LF-H and the plastein reaction-modified LF-H alone did not show detectable growth inhibition on BGC-823 cells at 1–3 mg/mL; however, the target product at the same dose levels inhibited cell growth, and showed higher activity than the mixture ( P  < 0.05). The target product at 2 and 3 mg/mL stopped cell cycle progression at the G0/G1-phase, induced DNA fragmentation , and showed apoptosis induction, which increased the number of apoptotic cells. Moreover, time- and dose-dependent responses were observed in these experiments. RT-PCR assay results indicated that exposure of the cells to the target product resulted in up- and down-regulated mRNA expression for 7 apoptosis-related genes, namely Bcl-2, Bcl-xl, Bad, Bax, caspase-3, caspase-6, and caspase-9. Thus, the plastein reaction increased in vitr o anticancer activities of LF-H with BGC-823 cells, and more importantly, both the plastein reaction and Trp incorporation contributed to enhanced activities.

CAS / MDL: 73-22-3
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BIOELECTROCHEMISTRY · 2019 · IF 4.474

Rapid recognition and determination of tryptophan by carbon nanotubes and molecularly imprinted polymer-modified glassy carbon electrode

Yiyong Wu,Peihong Deng,Yaling Tian,Ziyu Ding,Guangli Li,Jun Liu,Zavuga Zuberi,Quanguo He

A tryptophan (Trp) molecularly imprinted electrochemical sensor was fabricated by drop-coating an imprinted chitosan film on the surface of a glassy carbon electrode modified with multi-walled carbon nanotubes (MIP-MWCNTs/GCE). The surface morphology and electrochemical properties of the MIP-MWCNTs/GCE were characterized by scanning electron microscopy (SEM) and cyclic voltammetry (CV), respectively. The formation of hydrogen bonds between the functional polymer and the template molecule was confirmed by infrared spectroscopy . The electrochemical performance of the MIP-MWCNTs/GCE with Trp showed that the signal of the oxidation current of Trp obtained with MIP-MWCNTs/GCE was significantly enhanced relative to that of the uncovered GCE, indicating that the modified electrode can accelerate electron transfer and has strong selectivity for Trp. The experimental conditions were optimized in parallel, and under the optimal conditions, the MIP-MWCNTs/GCE showed a good linear relationship between the Trp oxidation peak current and Trp concentrations in the ranges of 2.0 nM–0.2 μM, 0.2 μM–10 μM and 10 μM–100 μM The limit of detection (LOD) was 1.0 nM (S/N = 3), and the modified electrode had good reproducibility and stability. Finally, the MIP-MWCNTs/GCE was successfully applied to the determination of Trp in the human serum samples.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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Biomolecules · 2019 ·Vol. 9 ·期 6 ·245 · IF 4.694

Facile Preparation of Fe3O4/C Nanocomposite and Its Application for Cost-Effective and Sensitive Detection of Tryptophan

Jun Liu,Shuai Dong,Quanguo He,Suchun Yang,Mei Xie,Peihong Deng,Yonghui Xia,Guangli Li

In this study, we reported facile synthesis of Fe3O4/C composite and its application for the cost-effective and sensitive determination of tryptophan (Trp) in human serum samples. Fe3O4/C composites were prepared by a simple one-pot hydrothermal method followed by a mild calcination procedure, using FeCl3∙6H2O as Fe3O4precursor, and glucose as reducing agent and carbon source simultaneously. The Fe3O4/C composite modified glassy carbon electrode (Fe3O4/C/GCE) was prepared by drop-casting method. The microstructure and morphology of Fe3O4/C composite was characterized by powder X-ray diffraction (XRD) and scanning electron microscopy (SEM), respectively. Due to large specific surface area and synergistic effect from Fe3O4nanoparticles and carbon coating, Fe3O4/C composite showed excellent electrocatalytic activity toward the oxidation of Trp. As a result, the proposed Fe3O4/C/GCE displayed superior analytical performances toward Trp determination, with two wide detection ranges (1.0–80 μM and 80–800 μM) and a low detection limit (0.26 μM, S/N = 3). Moreover, successful detection of Trp in human serum samples further validate the practicability of the proposed sensor.Keywords:Fe3O4/C composite;tryptophan;voltammetric detection;second derivative linear scan voltammetry

CAS / MDL: 73-22-3
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JOURNAL OF SOLID STATE ELECTROCHEMISTRY · 2017 ·Vol. 22 ·期 4 ·973-981 · IF 2.316

Highly selective tryptophan enantiomers electrochemical chiral sensor based on poly-lysine and functionalized multi-walled carbon nanotubes

Niu Xiaohui,Mo Zunli,Gao Huhu,Wang Ruijuan,Li Zhenliang,Meng Shujuan,Guo Ruibin

A novel electrochemical chiral sensor was reported for recognizing tryptophan enantiomers based on multi-walled carbon nanotubes functionalized by 3,4,9,10-perylenetetracarboxylic acid binding with the l -lysine (MWCNTs-PTCA-PLL) via electropolymerization. The electrochemical behaviors of the proposed sensors were then characterized by cyclic voltammetry (CV). Differential pulse voltammetries (DPVs) were applied to investigate the stereoselective recognition of tryptophan (Trp) enantiomers. d -Trp and l -Trp showed different responses in DPVs, and a larger selectivity was obtained from d -Trp. pH level and the effect of the incubation time on the chiral recognition were also investigated for optimizing experimental parameters. In addition, the results of analyzing percentage composition revealed this sensor was able to determine the enantiomeric mixtures. The novel strategy with high stability, good sensitivity, and selective characteristics had opened up a new avenue to recognize Trp enantiomers.

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TALANTA · 2022 · IF 6.556

3D Co-doped Ni-based conductive MOFs modified electrochemical sensor for highly sensitive detection of l-tryptophan

Wei Huang,Yao Chen,Lingyan Wu,Mei Long,Zhifeng Lin,Qianqian Su,Fuli Zheng,Siying Wu,Huangyuan Li,Guangxia Yu

L-tryptophan (Trp) is an essential amino acid for humans and plays crucial roles in many metabolic functions. Trp levels can be used for diagnosing different kinds of metabolic disorders and the symptoms associated with those diseases. Herein, a novel, simple and sensitive sensor based on 3D peony-like bimetallic conductive MOFs (Co–Ni-MOFs) was fabricated for the electrochemical determination of Trp. The bimetallic conductive MOFs were synthesized by a facile one-pot hydrothermal process. On account of the synergy between the Ni 2+ and Co 2+ ions, the bimetallic Co–Ni-MOFs showed excellent electrochemical performance, including good conductivity, large effective surface areas, and high electrocatalytic reactivity toward the oxidation of Trp. Consequently, the Co–Ni-MOFs-modified electrodes obtained a wide linear range from 10 nmol L −1 to 300 μmol L −1 and a low detection limit of 8.7 nmol L −1  (S/N = 3) for Trp. Additionally, the prepared sensor also displayed high selectivity, long-term stability and reproducibility. Moreover, the proposed sensor was successfully applied to determine the levels of Trp in the plasma of mice after cadmium intoxication.

CAS / MDL: 100-21-0 73-22-3
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COLLOIDS AND SURFACES B-BIOINTERFACES · 2021 · IF 5.268

Employing metformin-directed carbon dots with room-temperature phosphorescent towards the dual-channel detection of L-tryptophan

Zhiying Feng,Junchen Wang,Xin Chen,Jie Liu,Ying Zhu,Xiaoming Yang

Currently, carbon dots (CDs) with the eminent phosphorescence have been extensively concerned owing to their more widespread applications. Herein, we employed metformin as the carbon source and successfully synthesized one kind of room-temperature phosphorescence (RTP) CDs doped with the elements of N, P through a facile microwave method. Significantly, the RTP emission of CDs appeared while the solution was fixed on the filter paper. To be specific, the hydrogen bonds formed between CDs and the filter paper, which led to the restriction of molecular rotations and motions. Again, the non-radiation attenuation rate of the excited triplet state was reduced by rigidifying the whole system, thus inhibiting the non-radiative transitions and boosting their RTP emission CDs. Interestingly, the proposed CDs could serve as the RTP ink and was applied to paint various patterns and prepare CDs-PVA film with both fluorescence and phosphorescence. Moreover, both their fluorescence and phosphorescence of these CDs was obviously enhanced by introducing L -tryptophan, thus establishing an innovative dual-channel detection of L -trp. Besides, the detection mechanism was also explored, and the increased hydroxyl-groups enhanced their fluorescence of CDs through the radiative recombination by L -trp, while the phosphorescence was enhanced by the narrowed the energy gap (∆ E ST ), thus promoting the singlet-to-triplet intersystem crossing (ISC).

CAS / MDL: 74-79-3 52-90-4 108-78-1
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JOURNAL OF ELECTROANALYTICAL CHEMISTRY · 2021 · IF 4.464

Grain-like chiral metal-organic framework/multi-walled carbon nanotube composited electrosensing interface for enantiorecognition of Tryptophan

Xiaofeng Wei,Lishang Li,Huiting Lian,Xuegong Cao,Bin Liu

Due to the widespread application of chiral substances in current society, the electrochemical strategy to assemble chiral metal–organic frameworks (CMOFs) as sensors has shown great potential for sensitive enantiorecognition. In this paper, an efficient and highly selective electrochemical sensor was proposed based on multi-walled carbon nanotube (MWCNT) and CMOF, and successfully achieved sensitive chiral recognition of Tryptophan (Trp) enantiomers . Numerous MOFs in multiple synthesis conditions were investigated for a regular process to access the electrochemical chiral recognition. A variety of amino acids were introduced into the MOFs skeleton by a simple hydrothermal method for the enantio -specificity. Meanwhile the MWCNT smoothly integrated with the CMOF to form a functional electrosensing interface with the increase of conductivity. Based on the current ratio ( R cp ) of tryptophan enantiomers by different modified electrodes , a series of experimental conditions were optimized for the optimal chiral recognition performance of the CMOF/MWCNT-based sensor, finally reaching 2.9 times of ΔI L/D between enantiomers. In addition, D/ l -Trp showed a good linear relationship with the current in the range from 0.4 μM to 19 μM with the detection limit of 0.11 μM for l -Trp and 0.16 μM for d -Trp. The prepared composite-functionalized sensor owned the desired reproducibility and selectivity to identify Tryptophan enantiomers with robust chiral recognition. The research on the structure–activity relationship of chiral MOFs to Tryptophan enantiomers provides a new path to construct more electrochemical sensors for the application of enantiorecognition in pharmaceutical analysis.

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MICROCHEMICAL JOURNAL · 2021 · IF 4.821

Dual chiral selectors modified magnetic particles for enantioseparation of tryptophan and mandelic acid enantiomers in aqueous medium

Ya Liu,Li Jia

The realization of complete enantioseparation of a racemate in a single step is still a difficulty to be addressed. In this work, L-tryptophan (Trp) imprinted chitosan modified magnetic particles (Fe 3 O 4 @CS@MIP) were fabricated in a three-step process. The particles were spherical with an average diameter of 208.6 ± 9.6 nm. The thicknesses of CS and MIP layers were 3.9 ± 0.9 and 2.5 ± 1.4 nm, respectively. Fe 3 O 4 @CS@MIP possessed the chiral selectivity of CS and the stereoselective cavities of MIP. They were able to achieve the complete chiral separation of Trp racemate in aqueous solutions in a single step. The enantiomeric excess ( ee ) was almost 100%. The imprinting factor of this material for L-Trp was 5.75. Furthermore, Fe 3 O 4 @CS@MIP prepared using S-mandelic acid (S-MA) as a template also exhibited enantioselectivity toward S-MA with an ee value of 30%. The results demonstrate that the strategy for the preparation of chiral adsorbents has great potential in enantioseparation.

CAS / MDL: 10025-77-1 128446-35-5
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CHIRALITY · 2021 ·Vol. 33 ·期 4 ·176-183 · IF 2.437

Enantioselective recognition of tryptophan isomers with molecularly imprinted overoxidized polypyrrole/poly(p-aminobenzene sulfonic acid) modified electrode

Ling Gong,Shan Li,Zhengzhi Yin,Kelin Li,Jiawei Gu,Datong Wu,Yong Kong

Poly( p -aminobenzene sulfonic acid) (pABSA) was electrodeposited onto the surface of a glassy carbon electrode (GCE), which was then used for the preconcentration of l -tryptophan ( l -Trp) due to the electrostatic and π–π interactions between pABSA and l -Trp. Polypyrrole (PPy) was electrodeposited onto the surface of the l -Trp enriched pABSA, and then the l -Trp templates were removed, resulting in molecularly imprinted PPy/pABSA. To avoid the interference from the oxidation peak of PPy on the following electrochemical chiral recognition of Trp isomers, PPy was overoxidized by cyclic voltammetry (CV). The resultant molecularly imprinted overoxidized PPy (OPPy)/pABSA modified GCE exhibits higher affinity toward l -Trp than d -tryptophan ( d -Trp); that is, the oxidation peak current of l -Trp is greatly higher than that of d -Trp at the molecularly imprinted OPPy/pABSA modified GCE.

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JOURNAL OF ELECTROANALYTICAL CHEMISTRY · 2020 · IF 3.807

A novel pH sensor with application to milk based on electrochemical oxidative quinone-functionalization of tryptophan residues

Gengxin Hu,Nanxi Li,Yuwei Zhang,Hong Li

The electrochemical oxidative quinone-functionalization of tryptophan (Trp) residues, and the proton-coupled electron transfer properties between quinonized Trp (Trp=O) and its re-reduced species (Trp-OH) are investigated for potentiometric pH sensors. The Trp=O/Trp-OH couples are assembled on a graphite electrode using multiple cyclic voltammetry, and exhibit a pair of well-defined redox peaks at redox potential of 0.090 V (vs. SCE) at pH 7.0 and 298 K. The proton-coupled electron transfer properties of Trp=O/Trp-OH couples are dependent on electrode substrate material, incubation temperature and pH values, and Trp residue sources including amino acid, peptide and protein. The Trp=O/Trp-OH-based surface-confined exothermic electrode reaction rates show a decrease with increasing incubation temperature from 283 to 323 K at pH 5.0. Both of redox peak potential and open-circuit potential under optimum conditions have a good linear pH dependence between 1.0 and 12.0 with sensitivity of more than 52 mV pH  −1 and relative standard derivation of 1.5%. The proposed potentiometric pH sensor has significant advantages of low cost, good stability and reproducibility, and strong anti-interference ability. The present study shows a new approach to endow Trp, Trp-containing peptides and non-conjugated proteins with analogous proton-coupled electron transfer performance to prosthetic groups of quinoproteins for monitoring pH changes in milk samples.

CAS / MDL: 57-50-1 56570-89-9
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ANALYTICA CHIMICA ACTA · 2022 · IF 6.911

Interfacial superassembly of flower-like NiMn-LDH@poly-l-lysine composites for selective electrochemical sensing of tryptophan

Jing Qian,Juan Yang,Yuanyuan Zhang,Ting Zeng,Qijin Wan,Nianjun Yang

Development of sensitive, selective, and facile electrochemical analytical approaches to monitor tryptophan in different samples is of high significance. For such approaches, efficient electrodes play the key role. Herein, a NiMn-layered double hydroxide (LDH)@poly- l -lysine (PLL) composite has been prepared through in-situ electro-polymerization and further utilized to monitor tryptophan in medicament and biological systems. The as-synthesized NiMn-LDH@PLL composite is highly stable and features a flower-like morphology. It is found that the electron transfer rate of NiMn-LDH@PLL is greatly improved due to the introduction of PLL. The existing Lewis acid—base interaction between LDH and PLL contributes to the increase of unsaturated metal sites and endows this heterojunction composite with high electrocatalytic activity . Especially, the NiMn-LDH (2:1)@PLL composite displays much improved electrochemical response toward tryptophan sensing. This is due to reasonable balance between the outstanding electrocatalytic ability of nickel and the conductivity improvement caused by manganese species. On the other hand, the coordination promotion between NiMn-LDH and PLL is also conducive to improve the sensitivity of electrochemical response. The fabricated sensor exhibits wide linear response in the concentration ranges of 0.1–40 μM and 40–130 μM for tryptophan detection, along with a low detection limit of 52.7 nM. It further displays a high anti-interference ability for tryptophan monitoring even in the presence of other coexistent amino acids and small-sized biological molecules. This study provides a new way to employ LDHs as brilliant sensing platform to ensemble electrochemical sensors for the monitoring of biomolecules.

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