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tryptophan
JOURNAL OF PINEAL RESEARCH · 2024 ·Vol. 76 ·期 3 ·e12954 · IF 8.3

Gut microbially produced tryptophan metabolite melatonin ameliorates osteoporosis via modulating SCFA and TMAO metabolism

Yueqi Chen,Chuan Yang,Zihan Deng,Tingwen Xiang,Qingrong Ni,Jianzhong Xu,Dong Sun,Fei Luo

Osteoporosis (OP) is a severe global health issue that has significant implications for productivity and human lifespan. Gut microbiota dysbiosis has been demonstrated to be closely associated with OP progression. Melatonin (MLT) is an important endogenous hormone that modulates bone metabolism, maintains bone homeostasis, and improves OP progression. Multiple studies indicated that MLT participates in the regulation of intestinal microbiota and gut barrier function. However, the promising effects of gut microbiota-derived MLT in OP remain unclear. Here, we found that OP resulted in intestinal tryptophan disorder and decreased the production of gut microbiota-derived MLT, while administration with MLT could mitigate OP-related clinical symptoms and reverse gut microbiota dysbiosis, including the diversity of intestinal microbiota, the relative abundance of many probiotics such as Allobaculum and Parasutterella , and metabolic function of intestinal flora such as amino acid metabolism, nucleotide metabolism, and energy metabolism. Notably, MLT significantly increased the production of short-chain fatty acids and decreased trimethylamine N-oxide-related metabolites. Importantly, MLT could modulate the dynamic balance of M1/M2 macrophages, reduce the serum levels of pro-inflammatory cytokines, and restore gut-barrier function. Taken together, our results highlighted the important roles of gut microbially derived MLT in OP progression via the “gut-bone” axis associated with SCFA metabolism, which may provide novel insight into the development of MLT as a promising drug for treating OP.

研究领域: 药理学 · 微生物学 · 骨生物学 · 代谢组学
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CHEMICAL RESEARCH IN TOXICOLOGY · 2025 · IF 3.8

Region-Specific Metabolic Alterations in the Tryptophan Pathway in Cisplatin-Induced Acute Kidney Injury

Yue Feng,Ying Zhang,Jinxin Li,Junzhe Yu,Yuan Tian,Zunjian Zhang,Fengguo Xu,Pei Zhang

Cisplatin (DDP) is widely utilized in the clinical treatment of malignant tumors, but its effectiveness is significantly compromised by the adverse effects of acute kidney injury (AKI). Renal tubular cells are primarily responsible for DDP-induced AKI (DDP-AKI); however, the responses of heterogeneous renal tubular cells to DDP exposure have not been thoroughly explored. In this study, we employed a targeted metabolomics approach to investigate the metabolic responses of renal tubular cells in DDP-AKI rats. Tubular cells were isolated from the renal cortex and outer medulla, and a chemical derivatization-based liquid chromatography–tandem mass spectrometry (LC–MS/MS) metabolomics method was applied. Our findings revealed distinct metabolic profiles in tubular cells from the renal cortex and outer medulla, with outer medullary cells exhibiting greater sensitivity to DDP exposure. Further analyses identified the tryptophan pathway as a critical factor contributing to these regional differences. Additional functional investigations showed that intermediate metabolites of the tryptophan pathway alleviated DDP cytotoxicity in both cortical and outer medullary tubular cells primarily through modulation of the Bcl2/Bax and Caspase-3 pathway. This study enhances our understanding of the metabolic characteristics of tubular cells across heterogeneous renal regions in DDP-AKI and facilitates further exploration of the underlying mechanisms of DDP-induced nephrotoxicity.

CAS / MDL: 63562-33-4
研究领域: 药理学 · 肾病学 · 代谢组学 · 毒理学 · 细胞生物学
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Food Analytical Methods · 2025 · IF 3

Novel Silicon-Based Carbon Quantum Dots: An Efficient Fluorescent Probe for Precise Tryptophan Detection

Hu Jianan,Hong Dilong,Zhang Huan,Jiang Yuliang

Tryptophan, an essential amino acid for the human body, plays a crucial role in various physiological processes, including protein synthesis, fatty acid metabolism, enhancing energy levels, and being converted into neurotransmitters to regulate sleep and mood. It is also used in the prevention and treatment of pellagra. However, excessive intake of tryptophan can cause adverse effects, so detecting its concentration is of great significance. In this paper a silicon-based carbon quantum dot (N,Si-CDs) tryptophan probe was prepared. The structure and composition of N,Si-CDs were characterized by TEM, FT-IR, and XPS. Fluorescence studies revealed that N,Si-CDs exhibited high selectivity for tryptophan with minimal interference from other substances. There was a good Linear relationship between the fluorescence intensity of N,Si-CDs and the concentration of tryptophan in the range of 5–25 μM, and the detection Limit was as low as 19 nM. N,Si-CDs were successfully applied to detect tryptophan in complex Matrices such as honey, Yili milk powder, water-soluble vitamin C, sour plum soup, and lemon tea, with recovery rates ranging from 81.3% to 106.4%. Cell experiments demonstrated that N,Si-CDs had low toxicity to T24 cells and could be used for live-cell imaging. This N,Si-CDs shows great potential in fields such as food safety, environmental monitoring, and biomedical research.

CAS / MDL: 875-74-1
研究领域: 分析化学 · 纳米材料 · 生物传感器 · 食品安全 · 生物医学研究 · 环境监测
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ANALYTICAL CHEMISTRY · 2025 · IF 6.7

Quantification of Tryptophan Enantiomers in a Single Cell by β-Cyclodextrin-Modified Carbon Nanopipettes

Binghan Li,Xiaoyue Shen,Rujia Liu,Yingjie Zhao,Hongli Cao,Dengchao Wang

Tryptophan levels in the human body are closely related to disease development and metabolic processes, but identification and quantification of tryptophan enantiomers at the single-cell level is still very challenging now. Herein, the mono-(6-ethanediamine-6-deoxy)-β-cyclodextrin (β-CD)-modified carbon nanopipet (CNP) was fabricated, and high-enantioselective electrochemical detection of tryptophan was achieved. Interestingly, the selectivity of the prepared CNP toward l-tryptophan (l-Trp) and d-Tryptophan (d-Trp) could be modulated by adjusting the solution pH. Moreover, besides measuring the l-Trp concentration in a preserved cell environment, the fabricated tip could also be used to monitor the dynamics of l-Trp metabolism in the presence of representative amino acids. This work would offer a new approach to measure Trp enantiomers and reveal tryptophan metabolic pathways at the single-cell level.

CAS / MDL: 153-94-6 73-22-3
研究领域: 生物化学 · 分析化学 · 医学
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CLINICA CHIMICA ACTA · 2025 · IF 2.9

Targeted LC-MS/MS metabolomics reveals distinctive tryptophan pathway signatures in pneumocystis jirovecii pneumonia

Feng Chen,Xiaoxia Yang,Yayun Tan,Huanhuan Li,Yan Yan,Xiang Zhao,Chengfeng Qiu

Pneumocystis jirovecii pneumonia (PJP) is a high-mortality fungal infectious disease, and the changes in tryptophan metabolism and its diagnostic value in PJP remain unclear. This study aimed to elucidate the specific tryptophan metabolic profile in PJP patients by establishing and validating an LC-MS/MS method for the simultaneous quantification of tryptophan and its nine key metabolites in human serum. Serum samples from 46 PJP patients, 35 pulmonary tuberculosis (PTB) patients and 40 healthy controls were analyzed. The method achieved complete chromatographic separation within 5.5 min, with an extraction recovery rate > 95.8 % and matrix effects ranging from 86.0 % to 106.8 %, meeting the comprehensive validation criteria set by FDA and EMA guidelines. PJP patients exhibited significantly higher serum levels of 3-hydroxykynurenine (3−HK) compared to the PTB and healthy control groups (26.0 vs. 11.5 vs. 8.94 ng/mL, p  < 0.001), while levels of 5-hydroxytryptophan and indole-3-acetic acid were significantly lower ( p  < 0.05). The 3-Hydroxyanthranilic Acid/3-hydroxykynurenine ratio was also markedly reduced in the PJP group. ROC analysis demonstrated strong diagnostic performance for PJP with 3-hydroxykynurenine (AUC = 0.919), 5-hydroxytryptophan (AUC = 0.816), indole-3-acetic acid (AUC = 0.705), and the 3-Hydroxyanthranilic Acid/3-hydroxykynurenine ratio (AUC = 0.743). The validated LC-MS/MS method is rapid, sensitive, high-throughput and enables precise analysis of tryptophan metabolism. The distinct metabolic signature—particularly elevated 3-hydroxykynurenine, reduced 5-hydroxytryptophan and indole-3-acetic acid, and an altered 3-Hydroxyanthranilic Acid/3-hydroxykynurenine ratio—provides novel biomarkers for PJP diagnosis and offers new insights into its immunometabolic mechanisms.

研究领域: 传染病学 · 代谢组学 · 临床化学 · 免疫代谢 · 分析化学
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MICROCHIMICA ACTA · 2020 ·Vol. 187 ·期 8 ·1-7 · IF 6.232

Molecularly imprinted polymer functionalized silica nanoparticles for enantioseparation of racemic tryptophan in aqueous solution

Li Ling,Li Zhenqun,Jia Li

A method has been developed for preparation of surface molecularly imprinted polymer functionalized silica nanoparticles (SiO 2 @MPS@MIP). Firstly, the silica nanoparticles are prepared by a one-pot sol-gel method using tetraethylorthosilicate and 3-methacryloxypropyltrimethoxysilane as functional monomers. Next, the template molecule (L-Trp) is self-assembled with the functional monomer (acrylamide). Finally, SiO 2 @MPS@MIP are prepared using N,N′ -methylenebisacrylamide as the cross-linker. The prepared SiO 2 @MPS@MIP have an average diameter of about 6.3 ± 1.2 nm. They exhibit good selectivity toward L-Trp with an imprinting factor of 6.3. The adsorption isotherm data was well described by the Langmuir model. The maximum adsorption capacities of SiO 2 @MPS@MIP for L-Trp and D-Trp were calculated to be 11.1 ± 0.9 and 2.66 ± 0.16 mg g −1 , respectively. An enantiomer excess value of 100% was achieved after adsorption of racemic Trp by the material. The work suggests that SiO 2 @MPS@MIP are a promising material for enantioseparation of Trp racemate in aqueous media. Graphical abstract

研究领域: 材料科学 · 分析化学 · 纳米技术
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CHEMICAL ENGINEERING JOURNAL · 2026 · IF 12.5

Stereospecific chiral carbon dots hydrogel for dual-mode fluorescence/phosphorescence discrimination of tryptophan enantiomers

Shijing Li,Haoyue Wang,Nan Du,Hebing Pei,Nijuan Liu,Ruibin Guo,Zunli Mo

Chiral recognition is crucial for precision analysis and manufacturing in contemporary chemistry, pharmacology, and materials science, serving as a vital prerequisite for ensuring food and drug safety. This study successfully developed a chiral-selective hydrogel (CCHG) based on chiral carbon dots (CCDs), cellulose nanocrystals (CNCs), and β-cyclodextrin (β-CD) for the fluorescence/phosphorescence recognition of tryptophan (Trp) enantiomers. This hydrogel integrates the molecular recognition capability of β-CD, the photoluminescence properties of CCDs, and the signal amplification/structural support function of CNCs, establishing a stable gel-based sensing platform for L-tryptophan detection. Experimental results demonstrate a significant fluorescence enhancement effect for L-Trp in CCHG, while D-tryptophan exhibits negligible response. Furthermore, the system exhibits visible long-lived delayed emission (afterglow) lasting approximately 4 s after UV light removal, enabling visual discrimination between tryptophan enantiomers. Density functional theory (DFT) calculations were based on a simplified, β-CD-centered local recognition model. The results indicate that L-Trp exhibits a stronger binding affinity at this primary host-guest recognition site than D-Trp, providing theoretical support for the enantioselectivity observed experimentally. CCHG enables quantitative detection of L-tryptophan with a linear range of 100–800 μM and a detection limit of 1.21 μM. The method showed satisfactory spiked recoveries in Yellow River water and milk, together with good precision in 10-fold diluted serum. This study provides a new strategy for developing chiral recognition materials with high selectivity, visual readout capability, and improved mechanistic clarity.

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Frontiers in Microbiology · 2023 · IF 5.2

Study on secondary metabolites of endophytic fungus Diaporthe sp. AC1 induced by tryptophan analogs

Shikai Zhang,Qing Xu,Changbo Ji,Xiaoyu Han,Yang Zhou,Chao Liang,Linran Ma,Weijian Sun,Yanling Li,Zhengyou Yang,Fengchun Zhao,Yuan Tian

Small molecule-induced fermentation of the endophytic fungus Diaporthe sp. AC1 originated from Artemisia argyi was executed to investigate its secondary metabolites. It was fermented in a culture medium containing 5-hydroxytryptophan (5-HTP), 1-methyl-L-tryptophan (1-MT), and tryptamine (TA), respectively. The antibacterial activities of crude extracts against pathogenic bacteria and pathogenic fungi were determined by using the Oxford cup method, while the cytotoxicity of crude extracts against cancer cells was determined by using the MTT method. The results showed that the secondary metabolites of Diaporthe sp. AC1 induced by 1-MT exhibited optimal antibacterial activity and tumor cytotoxicity. The induction conditions of 1-MT were optimized, and the antibacterial activities and tumor cytotoxicity of crude extracts under different induction conditions were investigated. As indicated, the optimal moment for 1-MT addition was before inoculation and its optimal concentration was 0.25 mM. Under these conditions, Diaporthe sp. AC1 was fermented and approximately 12 g of crude extracts was obtained. The crude extracts were then separated and purified to acquire nine monomer compounds, including three new compounds ( 1 – 3 ) and six known compounds ( 4 – 9 ). The antibacterial activities of the compounds against pathogenic bacteria and pathogenic fungi were investigated by using the microdilution method, while their cytotoxicity against cancer cells was analyzed by using the MTT method. The results demonstrated that Compound 1 exhibited moderate antibacterial activities against Verticillium dahlia , Fusarium graminearum, and Botrytis cinerea , as well as a low inhibitory activity against Listeria monocytogenes . Nevertheless, Compound 1 showed significant cytotoxicity against five cancer cells, with IC 50 ranging from 12.26 to 52.52 μM. Compounds 2 and 3 exhibited negligible biological activity, while other compounds showed detectable inhibitory activities against pathogenic bacteria and cancer cells.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF MOLECULAR LIQUIDS · 2023 · IF 6

A specific purple–blue color reaction between tryptophan and tyrosine in concentrated acidic medium

Rui Wang,Jie Huang,Yubing Dong,Qiao Xu,Xiuyan Deng,Wenbin Jiang,Yaqin Fu

Electron transfer between tryptophan (Trp) and tyrosine (Tyr) is often accompanied with transient emission of visible blue-purple light, which is very common in numerous laser-induced photolysis experiments. However, recent experiments have shown that in the absence of pulse radiolysis, by mixing Trp and Tyr in concentrated aqueous hydrochloric acid can also produce a blue–purple color as it was observed in photolysis experiments. Unexpectedly, this color is quite stable in strong acid media (it can be kept at room temperature for at least a week). It is proposed that after initial formation of Trp radical products (TrpH ▪+ /Trp ▪ ) by the solvent radical oxidation, charge-transfer complexes were generated via electron transfer reactions between Trp radical products and phenol of Tyr or their directly hole-trapping mechanism, which exhibit a blue-purple color. In this work, HPLC analysis and density functional calculations show that there are loosely reversible associations in the charge-transfer complexes which can be stabilized by strong hydrogen bonding. A Trp radicals signal was observed but the intensity was not so strong as expected. This color reaction exhibits high selectivity towards Trp and Tyr, and thus it can be a convenient method for naked-eye identifying the coexistence of these two amino acids or protein modifications of related to them.

CAS / MDL: 1310-73-2
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ANALYTICAL CHEMISTRY · 2023 · IF 7.4

Highly Reliable Chiral Discrimination of Tryptophan Enantiomers through Two Different Modes: Electrochemistry and Temperature

Pengjing Jing,Tai Wen,Junyao Li,Wenrong Cai,Baozhu Yang,Yong Kong

Reliable chiral discrimination of enantiomers with simple devices is of great importance for chiral analysis. Here, a chiral sensing platform is developed for chiral discrimination through two different modes: electrochemistry and temperature. Au nanoparticles (AuNPs) are grown in situ on the nanosheets of MXene by utilizing the strong metal reduction ability of MXene, which can be further used for the anchoring of N-acetyl-l-cysteine (NALC), a commonly used chiral source, through Au–S bonds. Owing to the excellent electrical conductivity and photothermal conversion efficiency of MXene, the resultant MXene-AuNPs-NALC is applied in the construction of a chiral sensing platform for the discrimination of tryptophan (Trp) enantiomers through two different modes: electrochemistry and temperature. Compared with conventional single-mode chiral sensors, the proposed chiral sensing platform can integrate two different indicators (currents and temperature) into one chiral sensor, greatly improving the reliability of chiral discrimination.

CAS / MDL: 73-22-3 153-94-6
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Biomolecules · 2019 ·Vol. 9 ·期 7 ·294 · IF 4.694

A Simple and Efficient Molecularly Imprinted Electrochemical Sensor for the Selective Determination of Tryptophan

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

In this paper, a tryptophan (Trp) molecularly imprinted chitosan film was prepared on the surface of an acetylene black paste electrode using chitosan as the functional polymer, Trp as the template molecule and sulfuric acid as the crosslinking agent. The surface morphologies of non-imprinted and imprinted electrodes were characterized by scanning electron microscopy (SEM). The formation of hydrogen bonds between the functional polymer and the template molecule was confirmed by infrared spectroscopy. Some factors affecting the performance of the imprinted electrode such as the concentration of chitosan, the mass ratio of chitosan to Trp, the dropping amount of the chitosan-Trp mixture, the solution pH, and the accumulation potential and time were discussed. The experimental results show that the imprinted electrode exhibit good affinity and selectivity for Trp. The dynamic linear ranges of 0.01–4 μM, 4–20 μM and 20–100 μM were obtained by second derivative linear sweep voltammetry, and the detection limit was calculated to be 8.0 nM. The use of the imprinted electrode provides an effective method for eliminating the interference of potentially interfering substances. In addition, the sensor has high sensitivity, reproducibility and stability, and can be used for the determination of Trp in pharmaceutical preparations and human serum samples.Keywords:molecularly imprinted chitosan film;electrochemical sensor;tryptophan;selective determination

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TRANSACTIONS OF TIANJIN UNIVERSITY · 2017 ·Vol. 24 ·期 1 ·16-24 · IF 0

Morphological Control of Gold Nanoparticles by Green Synthesis Using l-Tryptophan and Other Additives

Sun Jinsheng,Wei Dongmei,Lv Hao

This study focuses on shape-controlled synthesis of gold nanoparticles, using the green reducing agent l -Tryptophan ( l -Trp), which is non-toxic and eco-friendly. This specific agent was investigated to realize certain morphology controlling effects by changing the relative growth rates among various crystal planes. Experimental samples were characterized by transmission electron microscope, UV–Vis spectrophotometer and X-ray diffraction (XRD) for size and morphological information. The effects of the specific additives of PVP ((C 6 H 9 NO) n ), CTAB (C 16 H 33 (CH 3 ) 3 NBr), and KBr were examined for their morphological control individually and synergistically in this system. Hexagonal gold nanoparticles were successfully obtained via the PVP/CTAB and PVP/KBr systems. Particular amounts of PVP/KBr produced various polyhedron structures, such as cubes, and others with triangular and rhombic straight-side cross sections.

CAS / MDL: 25249-54-1 9003-39-8
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