CHINESE JOURNAL OF CHEMISTRY
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2022
·Vol. 40
·期 15
·1821-1830
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IF 5.56
Xin Lu,Yijun Liu,Nan Qin,Chenxi Du,Yanyu Hu,Yao Chen,Haopeng Sun
Comprehensive Summary The cholinesterases are essential targets implicated in the pathogenesis of Alzheimer's disease (AD). We have identified tryptophan-tetrahydroisoquinoline derivatives as selective micro-nanomolar butyrylcholinesterase (BChE) inhibitors. Molecular docking was applied for the rational design and binding mode analysis. They were defined according to their target inhibitory activity, low cytotoxicity, predicted permeability through the blood-brain barrier (BBB), and in vivo cognitive improvement. Additionally, the preferred compound showed ability to decrease self-induced Aβ 1-42 aggregation and Aβ 1-42 induced SH-SY5Y cell injury. Altogether, these factors indicated their potential as unique lead compounds for AD treatment.
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Microbial Cell Factories
·
2022
·Vol. 21
·期 1
·1-9
·
IF 6.352
Wang Yingying,Chen Xueman,Chen Qiaoyu,Zhou Ning,Wang Xin,Zhang Alei,Chen Kequan,Ouyang Pingkai
Background l-Tryptophan (l-Trp) derivatives such as 5-hydroxytryptophan (5-HTP) and 5-hydroxytryptamine (5-HT), N-Acetyl-5-hydroxytryptamine and melatonin are important molecules with pharmaceutical interest. Among, 5-HT is an inhibitory neurotransmitter with proven benefits for treating the symptoms of depression. At present, 5-HT depends on plant extraction and chemical synthesis, which limits its mass production and causes environmental problems. Therefore, it is necessary to develop an efficient, green and sustainable biosynthesis method to produce 5-HT.Results Here we propose a one-pot production of 5-HT from l-Trp via two enzyme cascades for the first time. First, a chassis cell that can convert l-Trp into 5-HTP was constructed by heterologous expression of tryptophan hydroxylase from Schistosoma mansoni (SmTPH) and an artificial endogenous tetrahydrobiopterin (BH4) module. Then, dopa decarboxylase from Harminia axyridis (HaDDC), which can specifically catalyse 5-HTP to 5-HT, was used for 5-HT production. The cell factory, E. coli BL21(DE3)△tnaA/BH4/HaDDC-SmTPH, which contains SmTPH and HaDDC, was constructed for 5-HT synthesis. The highest concentration of 5-HT reached 414.5 ± 1.6 mg/L (with conversion rate of 25.9 mol%) at the optimal conditions (substrate concentration,2 g/L; induced temperature, 25℃; IPTG concentration, 0.5 mM; catalysis temperature, 30℃; catalysis time, 72 h).Conclusion sThis protocol provided an efficient one-pot method for converting. l-Trp into 5-HT production, which opens up possibilities for the practical biosynthesis of natural 5-HT at an industrial scale.
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
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2020
·
IF 3.232
Xinyi Zhu,Jie Zhao,Feifei Dai,Weitao Xu,Lixia Chen,Xin Xiao,Zhu Tao,Chao Zhang
Herein we present a simple fluorescence quenching method to selectively recognise and determine L-tryptophan (L-Trp) out of other 19 natural amino acids. Methylpillar[5]arene (MeP5), which is employed as a macrocyclic fluorescent probe, exhibits fluorescence activity in the solution of poor solvents because of aggregation-induced emission (AIE) effect. Fluorescence quenching of MeP5 in the solution of EtOH/CH 2 Cl 2 (98/2, v/v) was observed upon the addition of L-Trp whereas other 19 natural amino acids did not bring about obvious change in fluorescence intensity. 1 H NMR titration, fluorescence spectroscopy, mass spectrometry and theoretical analysis revealed that L-Trp can be encapsulated into the cavity of MeP5 to form a stable 1:1 host–guest inclusion complex which accounts for the quenching characteristics. The proposed procedure in this investigation offers an attractive and promising method for the selective detection of L-Trp in a mixture of natural amino acids.
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APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
·
2020
·Vol. 104
·期 6
·2481-2488
·
IF 3.53
Xu Da,Fang Mengjun,Wang Haijiao,Huang Lei,Xu Qinyang,Xu Zhinan
5-Hydroxytryptophan (5-HTP) is the precursor of the neurotransmitter serotonin and has been used for the treatment of various diseases such as depression, insomnia, chronic headaches, and binge eating associated obesity. The production of 5-HTP had been achieved in our previous report, by the development of a recombinant strain containing two plasmids for biosynthesis of L-tryptophan (L-trp) and subsequent hydroxylation. In this study, the L-trp biosynthetic pathway was further integrated into the E. coli genome, and the promoter strength of 3-deoxy-7-phosphoheptulonate synthase, which catalyzes the first step of L-trp biosynthesis, was engineered to increase the production of L-trp. Hence, the 5-HTP production could be manipulated by the regulation of copy number of L-trp hydroxylation plasmid. Finally, the 5-HTP production was increased to 1.61 g/L in the shaking flasks, which was 24% improvement comparing to the original producing strain, while the content of residual L-trp was successfully reduced from 1.66 to 0.2 g/L, which is beneficial for the downstream separation and purification. Our work shall promote feasible progresses for the industrial production of 5-HTP.
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CARBON
·
2020
·
IF 8.821
Ruanye Zhang,Ruxangul Jamal,Yi Ge,Wenli Zhang,Zongna Yu,Yinqiang Yan,Yingcheng Liu,Tursun Abdiryim
In this study, the functional groups (-OH,-SH) grafted poly (3,4-proplenedioxy thiophene)@nitrogen-doped carbon hollow spheres (N-HCS) composites were prepared by a chemical oxidative polymerization method for the electrochemical detection of tryptophan. The relationship between the structure and electrochemical performance were systematically studied. The improvement of synergetic effect resulted from strong non covalent bonding effect between the functional groups of N-HCS and polymers, as well as the interaction between functional groups (-OH,-SH) of polymers and small biomolecules enhanced the sensitivity and catalytic properties of the composites. The constructed sensors from composites of functionalized polymers@N-HCS modified glassy carbon electrodes displayed higher electrochemical sensing behavior for detection of tryptophan than unfunctionalized polymer@N-HCS. Furthermore, the composites of functional groups (-OH, –SH) grafted poly (3,4-proplenedioxy thiophene)@N-HCS exhibited a wide range (0.2–90 μM and 0.1–100 μM), low detection limit (4.16 nM and 9.2 nM) and good sensitivity (382.16 μAmM −1 cm −2 and 433.12 μAmM −1 cm −2 ), suggesting that the functional groups (-OH,-SH) grafted poly (3,4-proplenedioxythiophene)@N-HCS could be a promising and convenient material for the electrochemical sensing of tryptophan.
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MICROCHIMICA ACTA
·
2020
·Vol. 187
·期 8
·1-7
·
IF 6.232
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
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分析化学
·
纳米技术
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MICROCHEMICAL JOURNAL
·
2024
·
IF 4.9
Wenjing Wang,Yumin He,Suxiang He,Xiaoying Liu,Qing-wen Gui,Lei Deng,Hui Wang,Zhong Cao,Zemeng Feng,Benhai Xiong,Yulong Yin
L - Tryptophan (L-Trp), one of the essential amino acids, is crucial for human physiological homeostasis and a limiting amino acid in animal feed. In addition, L-Trp is a precursor of some important biomolecules in the body, such as pentraxin and melatonin. Disorders of L-Trp metabolism in the body may cause Alzheimer's or Parkinson's disease. Therefore, monitoring L-Trp levels in the body fluids quickly and accurately is essential. A colorimetric biosensor was developed for the rapid detection of L-Trp in solutions by coupling a novel, screened, and validated peptide aptamer with Au nanoparticles via the Au-S bond. The biosensor showed a wide linear detection range of 1 µM − 1000 µM, and in addition, it was simple to construct, and the reaction time was as short as 10 s. In the analysis of L-Trp in actual porcine serum samples, the relative standard deviations were 4.52 % to 3.01 % compared with those of the high-performance liquid chromatography method, and the spiked recoveries were 99.2 % to 100.2 %. This new type of recognition probe is likely to gain attention in the field of bioanalysis owing to its biocompatibility, ease of modification, and easy linkage to nanomaterials.
研究领域:
生物化学
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分析化学
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纳米技术
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MOLECULAR MEDICINE
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2025
·
IF 6.4
Yufei Deng,Xiaoying Hou,Qian Fang,Haiping Wang,Xiaoxuan Li,Zhiyong Hu,Zhaolu Liu,Limei Fan,Yunyi Liu,Zhengqi Fu,Xiji Shu,Binlian Sun,Lijun Huang,Yuchen Liu
Background FOLFOX is the recommended chemotherapy regimen for colorectal cancer (CRC), but its response rate remains low. Our previous studies have established a close relationship between gut microbiota and the anti-CRC effect of FOLFOX, though the underlying mechanisms remain unclear. Diet has been confirmed as a key factor influencing gut microbiota, and high-salt diets, representative of western dietary habits, has been shown to affect gut microbiota, immune function, and the risk of developing CRC. However, the impact of high-salt diets on the anti-CRC efficacy of FOLFOX remains unstudied. Therefore, we aimed to investigate the effect and mechanism of high-salt diets on the anti-CRC effect of FOLFOX. Methods We performed 16 S rRNA sequencing and T500 targeted metabolomics analysis on fecal samples from CRC patients and healthy adults. A CRC orthotopic xenograft mouse model was used to study the effect of a high-salt diet on FOLFOX’s anti-CRC efficacy. 16 S rRNA sequencing and non-targeted metabolomics were conducted on mouse fecal samples. Flow cytometry was used to assess immune cell infiltration in tumor and paracancerous tissues. A mouse macrophage conditioned medium system, with tryptophan metabolites, was employed to annotate the functional metabolites, followed by in vivo verification using the orthotopic xenograft mouse model. Results The structure and metabolic profiles of gut microbiota are significantly different between 9 healthy adults and 6 CRC patients. A high-salt diet significantly reduced the efficacy of FOLFOX in mice, with notable changes in gut microbiota and related metabolites. Correlation analysis revealed a significant relationship between gut microbiota, tryptophan metabolites and FOLFOX efficacy. Flow cytometry indicated that a high-salt diet altered macrophage infiltration (CD45 + F4/80 + ) in both the tumor and paracancerous tissues. In vitro experiments confirmed that the tryptophan metabolite SK reduced FOLFOX efficacy, while IPA enhanced it through macrophage-conditioned medium. In vivo, we verified that under a high-salt diet, SK inhibited the efficacy of FOLFOX, while IPA promoted it. Conclusion A high-salt diet reduces the anti-CRC efficacy of FOLFOX through gut bacterial tryptophan metabolism mediated macrophage immunomodulation. Supplementary Information The online version contains supplementary material available at 10.1186/s10020-025-01122-8.
研究领域:
肿瘤学
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微生物学
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免疫学
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代谢组学
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FOOD CHEMISTRY
·
2024
·
IF 8.5
Wan-zhen Li,Zi-liang Song,Jun-le Li,Jia-hui Yu,Du-jian Deng,Xiao-qing Cai,Martin J.T. Reaney,Zi-zhe Cai,Yong Wang
Linusorbs (LOs), significantly influence oil quality and sensory properties of flaxseed oil. Trp-containing LOs exhibit distinct oxidative behavior when γ-tocopherol (γ-T) is present. Polar fractions of crude flaxseed oil were stripped via silica absorption, and reintroduced (LO and γ-T) separately into the oil matrix to investigate their interaction during storage. Compared with crude oil, LOs account for 18.49% reduction of p -anisidine value, while LOs with γ-T contributed to most of the endogenous antioxidant effect in crude oil. γ-T was found to suppress oxidation of Trp-containing LO at early stage (Met form), while facilitate oxidation while at their mid-stage (MetO form, Methionine sulfoxide). In vitro oxidation shows that CLD more likely cleaved into peptide fragments, while few products retain intact ring structures. LC-MS/MS analysis and silicon simulation revealed proximity between MetO and Trp residues, facilitating inter- or intra-molecular reactions and ring structure rupture. Remarkably, the presence of γ-T facilitate these phenomena.
研究领域:
食品科学
·
生物化学
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MICROPOROUS AND MESOPOROUS MATERIALS
·
2026
·
IF 4.5
Hengchang He,Chenqiu Dai,Ji Zhu,Kaiyin Shi,Yapeng Lu,Peng Wang,Jianqiang Wang
An organo-bridged mesoporous silica with the framework of biomolecule Leucine-Tryptophan dipeptide (Leu-Trp-OBMS) is first constructed through soft-templating sol-gel method. • The dipeptide framework facilitated high naringenin loading through synergistic π-π stacking and hydrogen bonding, conforming to pseudo-second-order kinetics and the Freundlich isotherm. • The optimized 15%-Leu-Trp-OBMS-NAR composite with high SPF values demonstrated excellent UVB shielding performance. • The composite exhibited remarkable retention stability, with less than 3.4% of the loaded naringenin being released in simulated sweat within a 24 h period. The utilization of natural plant polyphenols, such as naringin, as sunscreen agents is hindered by their intrinsic instability. In this research, we devised a novel ultraviolet protection system through the encapsulation of naringin with high capacity (about up to 94.55 mg/g) within a dipeptide organo-bridged mesoporous silica (OBMS), which achieved outstanding UVB protection. A leucine-tryptophan dipeptide-based bridged organosilane precursor (Leu-Trp-BOSP) was synthesized and co-condensed with tetraethyl orthosilicate (TEOS) (5%-20% molar percentage of the precursor) under alkaline conditions, employing cetyltrimethylammonium bromide (CTAB) as a template. The resultant materials (x-Leu-Trp-OBMS) were characterized by XRD, FTIR, SEM, TEM, TG analysis and nitrogen adsorption-desorption analysis, which verified a well-defined mesoporous structure with type IV isotherms. The adsorption of naringin adhered to the pseudo-second-order kinetic model and the Freundlich isotherm, suggesting a multilayer chemisorption process predominantly dominated by cooperative π-π stacking and hydrogen bonding interactions between the tryptophan indole rings, dipeptide amide groups and the aromatic flavonoid core. The optimal formulation (15%-Leu-Trp-OBMS-NAR) attained a sun protection factor (SPF) of 4.45. In simulated sweat release tests, less than 3.4% of the loaded naringin was released over 24 h, demonstrating outstanding retention stability. These results indicate that dipeptide OBMS can serve as an effective scaffold for stabilizing naringin, presenting a promising platform for long-lasting sunscreen formulations. Download: Download high-res image (308KB) Download: Download full-size image
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MICROCHIMICA ACTA
·
2026
·Vol. 193
·期 4
·268
·
IF 5.4
Liu Yan,Yin Zhaojiang,Wang Xin,Li Binghui,Chen Quan,Chen Yuqiang,Tu Peng,You Mei,Li Han,Zhong Zubin,Liao Fusheng,Fan Hao,Zhang Jing
A chiral ruthenium probe (Ru-phe) for determination of amino acids was constructed by conjugating L-phenylalanine to a Ru-MOF precursor via EDC/NHS activation. The stereogenic center and aromatic side chain of L-Phe establish a chiral microenvironment that facilitates π–π stacking and hydrophobic interactions with tryptophan, thereby enabling efficient enantioselective recognition. The Ru-phe electrochemiluminescence (ECL) sensing platform achieved broad linear quantification ranges—0.1 nM – 1 mM for L-Trp and 10 nM – 1 mM for D-Trp. The detection limits were 0.06 nM for L-Trp and 13 nM for D-Trp. Moreover, the method showed strong reproducibility in human serum samples, with relative standard deviations (RSDs) of 0.9–1.8% for L-Trp. Machine-learning-assisted classification further improved enantiomer discrimination accuracy to 96%. Overall, this work introduces an efficient and highly sensitive ECL approach that enables practical enantiomeric determination of tryptophan, offering strong potential for clinical monitoring.
Section
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CHEMICAL ENGINEERING JOURNAL
·
2026
·
IF 12.5
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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