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BIOCHEMICAL ENGINEERING JOURNAL · 2023 · IF 3.9

Chirality of tyrosine controls biofilm formation via the regulation of bacterial adhesion

Hongyi Li,Yifu Wang,Xinxin Zhao,Zhen Yan,Chao Song,Shuguang Wang

Biofilm is the main cause of membrane biofouling and microbial corrosion . One of the most efficient strategies for biofilm reduction is inhibiting bacteria adhesion. In this study, we selected D -tyrosine to inhibit the adhesion of Escherichia coli , and the molecular response and metabolic pathways of E. coli were explored with transcriptome analysis . D -tyrosine could obviously inhibit the bacterial adhesion via lowering the adhesion force. The number of extracellular proteins decreased by 45% in the presence of D -tyrosine, leading to less hydrophobicity and autonomous aggregation of cells. Furthermore, transcriptome analysis showed that the inhibitory ability of D -tyrosine to the adhesion of E. coli decreased with time. At the initial stage, D -tyrosine could regulate tryptophan , curli, peptidoglycan , and adhesion-like protein synthesis , leading to less extracellular protein and lower cell hydrophobicity, and thus reduce cell aggregation and surface adhesion. This study provides a better understanding for the roles of D -amino acids in bacterial adhesion and develops a new strategy for biofilm reduction to mitigate membrane biofouling and microbial corrosion.

CAS / MDL: 556-02-5 60-18-4
研究领域: 微生物学 · 环境科学
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MICROCHEMICAL JOURNAL · 2023 · IF 4.8

2D Zn-MOF fluorescence probe for detecting D-tyrosine in methanol or aqueous systems

Ying-ying Hu,Xiao-qin Wu,He-ping Shi,Xue-hong Wei

The nature of amino acids as the building blocks of proteins leading to detection and identification is a current hot topic. Therefore, {[Zn 3 (L − ) 2 (HBTC 2− ) 2 ]·2H 2 O·CH 3 CN} n ( Zn-1 , H 3 BTC = 1,3,5-benzenetricarboxylic acid, HL = 6-aminonicotinic acid, CH 3 CN = acetonitrile), a 2D Zn-MOF which can sensitively detect and selectively recognize D -tyrosine was synthesized by solvothermal method . Identification of D -tyrosine was determined by increasing fluorescence intensity and red-shifting of the emission wavelength . Zn-1 is highly stable in methanol (MeOH) and aqueous solution (H 2 O), so it was dissolved in them as fluorescence probes, namely Zn-1/MeOH probe and Zn-1/H 2 O probe , respectively. The two probes worked for lower limits of detection, 8.93 × 10 −2 μM for Zn-1/MeOH probe and 79.70 × 10 −2 μM for Zn-1/H 2 O probe . The Stern-Volmer quenching constant of Zn-1/MeOH probe is 1.28 × 10 4 M −1 and of Zn-1/H 2 O probe is 4.55 × 10 2 M −1 . In addition, the two probes still show excellent immunity to interference under the interference of 18 amino acids. Zn-1/H 2 O probe was also applied to the determination of D -tyrosine in real milk samples with good results. This study provides a fast, simple, convenient and relatively accurate method for detecting D -tyrosine.

CAS / MDL: 75-05-8
研究领域: 生物化学 · 分析化学 · 材料科学
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CHEMICAL ENGINEERING JOURNAL · 2016 · IF 5.31

Polyethersulfone membranes modified with D-tyrosine for biofouling mitigation: Synergistic effect of surface hydrophility and anti-microbial properties

Bei-Bei Jiang,Xue-Fei Sun,Lin Wang,Si-Yu Wang,Ru-Dong Liu,Shu-Guang Wang

Biofouling is a critical issue in membrane separations . Development of novel approaches for biofouling mitigation is of crucial importance for membrane-based technologies . In this research, D-tyrosine was immobilized on a polyethersulfone (PES) ultrafiltration membrane (UF) to mitigate biofouling with the synergistic effects of surface hydrophilicity and anti-microbial properties. Results showed that the grafting of D-tyrosine increased the surface hydrophilicity and imparted a smoother surface to the membrane without altering its transport properties. During bovine serum albumen (BSA) filtration tests, the unified membrane fouling index (UMFI) of D-tyrosine-polydopamine (PDA)/PES membrane was only 0.00162, probably half of the PDA/PES membrane’s UMFI without D-tyrosine. The flux recovery ratio (FRR) of the D-tyrosine-PDA/PES membrane was up to 79%, higher than the virgin PES membrane. Moreover, the D-tyrosine-PDA/PES membrane showed better anti-biofouling performance when inoculated with E. coli culture. The proposed membrane surface modification technique paves the way toward realization of biological control for mitigating biofouling by simultaneously enhancing the anti-adhesive and antimicrobial properties of the membrane.

CAS / MDL: 62-31-7 556-02-5
研究领域: 环境科学 · 材料科学 · 生物学
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Journal of Environmental Chemical Engineering · 2023 · IF 7.7

Biofouling mitigation by D-tyrosine in membrane bioreactor: Short-term performance

Xinying Su,Jintao Luo,Yu Wang,Jinghao Dong,Yu Tian

D -amino acids can inhibit the formation of biofilm without affecting bacterial growth, which is a new strategy to control membrane biofouling. This paper investigated the effects of D -tyrosine on the performance of membrane bioreactor (MBR) during short-term operation. The results showed that the critical flux of activated sludge in MBR increased with the existence of D -tyrosine. The removal efficiencies of wastewater were not affected by D -tyrosine. The fouling propensities of soluble microbial products (SMP) in both MBRs were almost the same. Extracellular polymeric substance (EPS) in D -tyrosine group exhibited weaker fouling propensity. Further research indicated that the addition of D -tyrosine did not have a significant impact on SMP. D -tyrosine lead to the reduction of EPS polysaccharides and the great fluctuation of EPS protein. Microbial community analysis demonstrated that the addition of D -tyrosine changed the microbial community structure in MBR, which might be one of the reasons for the change of EPS.

CAS / MDL: 556-02-5
研究领域: 环境工程 · 微生物学
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JOURNAL OF MEMBRANE SCIENCE · 2023 · IF 9.5

Polydopamine and d-tyrosine-functionalized PTFE membrane for membrane distillation of secondary effluent: Fouling mitigation and mechanism

Yang Li,Bingxuan Ji,Ziyang Chen,Zhenghua Zhang

Secondary effluent from municipal wastewater treatment plants can be used to produce reclaimed water through membrane distillation (MD), providing a potential solution to the current global water crisis. However, membrane fouling over extended periods of operation reduces the separation performance of MD systems and significantly shortens the operational life-span of the membrane. Herein, in order to overcome these limitations, a novel surface-modified PTFE membrane was fabricated by depositing polydopamine and grafting dextro ( d )-tyrosine (Tyr/PDA@PTFE). This synergistic coating was designed to reduce surface hydrophobicity of the PTFE membrane and provide anti-adhesive properties for bacteria, while enhancing flux and anti-fouling performance during MD. The Tyr/PDA@PTFE membranes demonstrated enhanced MD performance and the Tyr-300/PDA@PTFE membrane (with d -tyrosine coating solution concentration of 300 μM) exhibited the best MD performance during direct contact membrane distillation (DCMD) of the secondary effluent, with the highest flux (49.1 LMH) compared with the pristine PTFE membrane (34.7 LMH), achieving a flux increase of 41.5%. Long-term DCMD operation showed that the Tyr-300/PDA@PTFE membrane exhibited improved anti-fouling performance compared with the pristine PTFE membrane, with 43.8% flux decay observed after three cycles of use, while the pristine PTFE membrane was unable to complete three cycles of use with an 87.2% decrease in flux observed by middle of the third round. The quality of permeate formed by the Tyr/PDA@PTFE membranes during MD, indicated that they could be operated stably for three cycles of use over a 40 h period, intercepting organic matter in the feed solution. The Tyr-300/PDA@PTFE membrane was especially effective for the removal of low molecular weight and humus-like substances, achieving rejection rates of 89.5% and 86.7%, respectively. Additionally, the Tyr/PDA@PTFE membrane carried the more negative charge and exhibited a high level of resistance to bio-adhesion. This study demonstrates the feasibility of use of this novel Tyr/PDA@PTFE membrane in MD, for the effective treatment of secondary effluent from wastewater treatment plants and the production of reclaimed water.

CAS / MDL: 556-02-5
研究领域: 环境工程 · 水处理 · 膜科学 · 废水回用
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Heliyon · 2023 · IF 4

d-tyrosine enhances disoctyl dimethyl ammonium chloride on alleviating SRB corrosion

Jingyi Zhou,Hongyi Li,Shichu Gong,Shuguang Wang,Xianzheng Yuan,Chao Song

Microbiologically influenced corrosion (MIC) caused by sulfate reducing bacteria (SRB) is a serious challenge in many industries, but biofilm greatly decreases the toxicity of bactericides to cell inside. d-amino acids are potential enhancers for bactericides due to their excellent performance on biofilm inhibition. However, the mechanism of d-amino acid cooperating with bactericides for MIC inhibition is still unknown. In this study, d-tyrosine(D-Tyr)and disoctyl dimethyl ammonium chloride (DDAC) were selected as the typical d-amino acid and bactericide, respectively, to evaluate their synergetic inhibition on the corrosion caused by Desulfovibrio vulgaris . D-Tyr obviously enhanced the role of DDAC in inhibiting corrosion with high corrosion inhibition efficiency at 77.23 %. The attachment of EPS and live cells on the coupon surface decreased in the presence of D-Try, leading to more cells directly exposed to DDAC. Besides, D-Try decreased the amount of live cells on the surface and thus reduced the utilization of Fe by SRB and corrosion current. Moreover, dead cells settling to the coupon surface may form a protective lay to retard the contact between live SRB and Fe, leading to slow cathode reaction and less corrosion. Therefore, D-Tyr can reduce the coverage of biofilm, thereby reducing its protective effect on SRB and achieving better corrosion inhibition effect. This work provides a new strategy for improving bactericides and inhibiting MIC.

研究领域: 腐蚀科学 · 微生物学 · 材料科学
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Asian Journal of Pharmaceutical Sciences · 2024 · IF 10.7

Charge Adaptive Phytochemical-based Nanoparticles for Eradication of Methicillin-Resistant Staphylococcus aureus Biofilms

Xilong Cui,Fanhui Liu,Shuang Cai,Tingting Wang,Sidi Zheng,Xinshu Zou,Linlin Wang,Siqi He,Yanhua Li,Zhiyun Zhang

The intrinsic resistance of MRSA coupled with biofilm antibiotic tolerance challenges the antibiotic treatment of MRSA biofilm infections. Phytochemical-based nanoplatform is a promising emerging approach for treatment of biofilm infection. However, their therapeutic efficacy was restricted by the low drug loading capacity and lack of selectivity. Herein, we constructed a surface charge adaptive phytochemical-based nanoparticle with high isoliquiritigenin (ISL) loading content for effective treatment of MRSA biofilm. A dimeric ISL prodrug (ISL-G2) bearing a lipase responsive ester bond was synthesized, and then encapsulated into the amphiphilic quaternized oligochitosan. The obtained ISL-G2 loaded NPs possessed positively charged surface, which allowed cis-aconityl-D-tyrosine (CA-Tyr) binding via electrostatic interaction to obtain ISL-G2@TMDCOS-Tyr NPs. The NPs maintained their negatively charged surface, thus prolonging the blood circulation time. In response to low pH in the biofilms, the fast removal of CA-Tyr led to a shift in their surface charge from negative to positive, which enhanced the accumulation and penetration of NPs in the biofilms. Sequentially, the pH-triggered release of D-tyrosine dispersed the biofilm and lipase-triggered released of ISL effectively kill biofilm MRSA. An in vivo study was performed on a MRSA biofilm infected wound model. This phytochemical-based system led to ∼2 log CFU (>99%) reduction of biofilm MRSA as compared to untreated wound ( P < 0.001) with negligible biotoxicity in mice. This phytochemical dimer nanoplatform shows great potential for long-term treatment of resistant bacterial infections.

研究领域: 纳米技术 · 药学 · 微生物学 · 生物医学工程
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Advanced Healthcare Materials · 2023 · IF 10

A Multifunction Hydrogel-Coating Engineered Implant for Rescuing Biofilm Infection and Boosting Osseointegration by Macrophage-Related Immunomodulation

Yao Ding,Genhua Liu,Shaopeng Liu,Xuan Li,Kun Xu,Peng Liu,Kaiyong Cai

Innovative methodologies combined with scavenging reactive oxygen species (ROS), alleviating oxidative stress damage and promoting macrophage polarization to M2 phenotype may be ideal for remodeling implant-infected bone tissue. Herein, a functionalization strategy for doping Tannic acid- d -tyrosine nanoparticles with photothermal profile into the hydrogel coating composed of konjac gum and gelatin on the surface of titanium (Ti) substrate is accurately constructed. The prepared hydrogel coating exhibits excellent properties of eliminating biofilm and killing planktonic bacteria, which is based on increasing susceptibility to bacteria by the photothermal effect, biofilm-dissipation effect of D-tyrosine, as well as the bactericidal effect of tannic acid. In addition, the modified Ti substrate has effectively alleviated proinflammatory responses by scavenging intracellular excessive ROS and guiding macrophages polarization toward M2. More interesting, conditioned medium from macrophage indicates that paracrine is conducive to osteogenic proliferation and differentiation of mesenchymal stem cells. Results from rat model of femur infection in vivo demonstrate that the modified Ti implant significantly eliminates the residual bacteria, relieves inflammation, mediates macrophage polarization, and accelerates osseointegration. Altogether, this study exhibits a new perspective for the development of advanced functional implant with great application potential in bone tissue regeneration and repair.

CAS / MDL: 1401-55-4
研究领域: 生物材料 · 生物医学工程 · 免疫学 · 骨科 · 组织工程
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CHEMICAL ENGINEERING JOURNAL · 2024 · IF 13.3

Construction of chiral nanozymes with high enantioselectivity for visual detection via smartphone-based paper sensors

Qing Li,Congnan Wu,Jiaxing Zhang,Rongxin Su,Yuefei Wang,Wei Qi

The development of enantioselective nanozymes holds profound significance in synthesizing chiral compounds and elevating analytical precision. Herein, we have synthesized chiral gold/iron hierarchically organized particles (Cys@Au/Fe Hops) possessing peroxidase-like catalytic activity, through a one-pot method using cysteine as a chiral inducer. The nanozymes exhibited remarkable enantioselective catalytic activity to 3,4-dihydroxy-phenylalanine (DOPA) enantiomer. Notably, L -Cys@Au/Fe Hops, comprising right-handed helical nanopetals, exhibited elevated catalytic efficiency for L -DOPA over D -DOPA, whereas the reverse held for D -Cys@Au/Fe Hops. The molecular dynamics simulations demonstrated hydrogen bonding interactions between the active site and substrate, thereby revealing how steric effects affected the enantioselective catalysis of chiral DOPA by L/D -Cys@Au/Fe Hops. Moreover, the chiral nanozymes were developed into a test paper sensor due to their exceptional stability, which can achieve the visual detection of DOPA enantiomer combined with a smartphone platform. This work is significant in advancing the design and practical utility of highly selective enzyme mimics.

研究领域: 生物化学 · 纳米技术 · 分析化学
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TALANTA · 2024 · IF 5.6

Colorimetric discrimination and spectroscopic detection of tyrosine enantiomers based on melamine induced aggregation of l-cysteine/Au nanoparticles

Haibo Chen,Yan Luo,Wenrong Cai,Laidi Xu,Junyao Li,Yong Kong

Au nanoparticles (AuNPs) are decorated by l -cysteine (L-Cys), and the resultant chiral L-Cys/AuNPs can be used for colorimetric discrimination and spectroscopic detection of the tyrosine (Tyr) enantiomers . Melamine (Mel) can induce the aggregation of the L-Cys/AuNPs through ligand exchange, leading to a distinct color change from wine red to purple. Owing to the same rotatory direction of L-Cys/AuNPs and L-Tyr, the L-Cys/AuNPs exhibit a significantly higher binding affinity toward L-Tyr than D-Tyr, and thus the Mel induced aggregation of the L-Cys/AuNPs is greatly alleviated by the protection from the L-Tyr protective layer. Therefore, the Tyr enantiomers can be simply discriminated by naked eyes. In addition, the absorbance of the aggregated L-Cys/AuNPs at ∼630 nm increases linearly with decreasing concentrations of L-Tyr ranging from 10 nM to 1 mM due to the weakened protection effect from L-Tyr, and thus spectroscopic detection of L-Tyr can also be accomplished by the developed L-Cys/AuNPs with a limit of detection (LOD) of 5.3 nM.

CAS / MDL: 52-90-4 556-02-5 60-18-4
研究领域: 生物化学 · 分析化学 · 纳米技术
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ANALYTICAL CHEMISTRY · 2026 · IF 7.3

Soft-Chain-Induced Ultrahigh-Resolution Chiral Separation of Amino Acids via Bimetallic Immobilization in MALDI-TIMS-MS

Simin Zhang,Xiangfeng Chen,Yaping Shi,Xiangyu Zhu,Zongwei Cai

As bioactive compounds, chiral amino acids (AAs) have been demonstrated to play pivotal roles in different physiological processes, thereby influencing human health. The assessment of the relative enantiomeric ratio through analytical methods is essential for indicating the abnormal status of disease progression, which drives the development of effective methods for resolving and identifying enantiomers. This work presents a robust strategy for the ultrahigh-resolution analysis of chiral AAs using MALDI-TIMS-MS. By employing a chiral derivatization process using S-NIFE and stabilizing the soft chain of the derivatization reagent with bimetal ion addition, the separation of 19 pairs of proteinogenic AAs was successfully achieved. This method not only demonstrates outstanding separation capability but also proves its efficiency in determining enantiomeric ratios, extending its applicability to real sample analysis.

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ACS Applied Nano Materials · 2025 · IF 5.5

Trypsin Electrochemical Biosensor Based on the Chiral Recognition Capability of Gold Nanoparticles/Bovine Serum Albumin

Junyao Li,Yujie Wang,Chen Jin,Zheng-Zhi Yin,Hongyu Zhang,Peiming Liu,Wenrong Cai,Datong Wu,Fengxiang Yin,Yong Kong

Trypsin (TRY) is an essential digestive enzyme, and its concentration level is regarded as a reliable indicator of pancreatic diseases. In this work, a highly sensitive and stable TRY electrochemical biosensor has been developed by taking advantage of the regulatable chiral recognition capability of gold nanoparticles/bovine serum albumin (AuNPs/BSA). Bovine serum albumin (BSA) is a protein with intrinsic chirality, which can be utilized to coat gold nanoparticles (AuNPs) through Au–S bonds and form AuNPs/BSA. Notably, the chiral recognition capability of AuNPs induced by d-Cysteine toward tyrosine (Tyr) enantiomers is opposite to that of BSA. For AuNPs/BSA, the chiral recognition capability is dominated by BSA adsorbed on the surface of AuNPs. By introducing varying concentrations of TRY, the structural integrity of BSA on the surface of AuNPs/BSA is gradually disrupted, resulting in a reversal of its chiral discrimination capability toward Tyr enantiomers, thereby enabling precise regulation of the chiral recognition capability of AuNPs/BSA relying on the specific hydrolysis of TRY. Therefore, the concentration of TRY can be sensitively detected by measuring the different recognition efficiencies of AuNPs/BSA/TRY toward Tyr enantiomers, namely, the peak current ratio of l-tyrosine to d-tyrosine (IL/ID) in differential pulse voltammetry. Additionally, the integration of dual electrochemical signals is conducive to enhancing the stability of the TRY detection results, manifesting the considerable application potential of the TRY electrochemical biosensor in biological analysis and medical diagnostics.

研究领域: 生物分析化学 · 电化学传感器 · 纳米生物技术 · 医学诊断 · 蛋白质工程
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