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JOURNAL OF FOOD COMPOSITION AND ANALYSIS · 2024 · IF 4

Hybrid polymer dots with isothiocyanate functional groups for rapid sensing tyramine in aquatic products

Gan Wu,Qi Cheng,Zhaoyang Ding,Jing Xie

Biogenic amines are critical indicators for the quality and safety of aquatic products, and biogenic amine poisoning could threaten human health. Therefore, it is crucial to develop easily operated and efficient analytical sensors for strict tyramine detection. To address this need, ratiometric fluorescent sensors have been developed for the detection of tyramine. F8BT-RBI polymer dots and PVK-FITC polymer dots were prepared by the semiconductor polymers Poly [(9, 9-di-n-octylfluorenyl-2, 7-diyl)-alt-(benzo [2,1,3] thiadia-zol-4, 8-diyl)] (F8BT) and Poly (9-vinylcarbazole) (PVK), combined with rhodamine B isothiocyanate (RBI) and fluorescein isothiocyanate (FITC) through reprecipitation methods. The ratiometric fluorescent sensors rely on the changes in fluorescence intensity in dual channels caused by the intramolecular charge transfer (ICT) resulting from the reaction between isothiocyanate dyes and tyramine. This approach enables accurate detection of tyramine content within specific linear ranges. For instance, PF8BT-RBI covers a range of 2.74–20.6 mg L −1 with a limit of detection (LOD) of 0.14 mg L −1 , while PPVK-FITC covers 20.6–61.7 mg L −1 with an LOD of 0.59 mg L −1 . PF8BT-RBI and PPVK-FITC had potential for fluorescence detection of tyramine, and were applied in the detection of tyramine in aquaculture water and tuna. By utilizing Pdots and isothiocyanate dyes, these sensors can meet the demand for ensuring the freshness and safety of aquatic products.

CAS / MDL: 51-67-2
研究领域: 食品安全 · 分析化学 · 生物传感
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EUROPEAN POLYMER JOURNAL · 2023 · IF 6

A highly thermally stable benzoxazine resin derived from norbornene and natural renewable tyramine and furfurylamine

Yi Yang,Yin Lu,Kan Zhang

Highly thermally stable polymeric materials synthesized from renewable resources are highly desirable in many high-performance fields due to the sustainable development of human beings. Herein, a new norbornene-containing monobenzoxazine thermosetting resin ( HPTM-fa ) exhibiting very high thermal stability has been prepared using natural bio-resourced tyramine and furfurylamine as starting materials. The structural details of HPTM-fa were characterized by FT-IR, NMR as well as high-resolution mass spectroscopies. The polymerization behaviors of cross-linkable norbornene , oxazine ring, and furan groups in HPTM-fa were investigated by DSC and in situ FT-IR analyses. In addition, the polybenzoxazine thermoset derived from this newly obtained bio-based mono-benzoxazine resin showed very high thermal stability with a T d5 of 413 °C and a glass transition temperature of 290 °C. The outstanding performance of thermoset based on HPTM-fa evidences its potential applications in the design of highly thermally stable polymeric materials.

CAS / MDL: 617-89-0 51-67-2
研究领域: 材料科学 · 化学工程
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MICROCHEMICAL JOURNAL · 2020 · IF 3.594

In-situ preparation of molecularly imprinted fluorescent sensing test strips for on-site detection of tyramine in vinegar

Dan Qiao,Zhen Zhang,Lingshuang Wang,Wei Sheng,Qiliang Deng,Shuo Wang

Test strips as one of micro-devices are widely concerned in the fields of point-of-care detection and in-field diagnosing. For the purpose of on-site detection of tyramine, a carbon dots-molecularly imprinted fluorescent sensing test strip with high selectivity has been successfully obtained via a rapid in-situ preparation procedure (about 2.5 h). Here, the layer composed of carbon dots-molecularly imprinted polymer (CDs-MIP) with the function of the recognition and signal transduce has been formed on the surface of the filter paper strips via the sol-gel method. The developed test strip displayed a high specificity (Imprinting factor, IF = 4.96); and its fluorescence emission was quenched linearly with the increase of tyramine concentration from 0.5 to 10.0 mg L −1 . The limit of detection (LOD) is 0.059 mg L −1 (3 σ/s ). The application potential was verified by sensing of tyramine in rice vinegar and white rice vinegar with the recoveries of 90.9-104.4% (RSD < 5.8%). Many advantages including a rapid preparation and high selectivity make the fluorescence strip suitable for on-site detection of tyramine. In addition, the preparation procedure can also be easily transferred to the preparation of the fluorescence strip toward other targets.

CAS / MDL: 78-10-4
研究领域: 分析化学 · 食品科学
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Frontiers in Physiology · 2020 · IF 3.367

Role of Biogenic Amines in Oviposition by the Diamondback Moth, Plutella xylostella L

Li Fan,Li Ke,Wu Li-Juan,Fan Yong-Liang,Liu Tong-Xian

Oviposition is an important reproductive behavior that is triggered by mating in insects, and biogenic amines might be involved in its regulation. The effects of biogenic amines on oviposition have only been studied in a few insect species, and the findings to date have not been conclusive. In addition, there are few studies on the effects of biogenic amines on oviposition of the diamondback moth, Plutella xylostella L. Here, we tested how mating and biogenic amines regulate oviposition of P. xylostella by injecting amines and amine receptor antagonists into virgin and mated females and counting the number of eggs laid afterward. Biogenic amines of octopamine and tyramine could induce virgin adults of P. xylostella to lay eggs, while dopamine and serotonin had no such effect on oviposition. Furthermore, the octopamine antagonists mianserin, epinastine, and phentolamine inhibited oviposition by mated females. The tyramine antagonist yohimbine, dopamine antagonist SCH23390, and serotonin antagonist ketanserin did not block oviposition by mated females, and octopamine and tyramine-inducing oviposition by virgin females could be inhibited by the octopamine antagonists mianserin and epinastine instead of the tyramine antagonist yohimbine. We conclude that octopamine and its receptors are involved in mating-triggered oviposition in P. xylostella, while tyramine acts as a subsidiary. Further, the inducing effect of tyramine on oviposition is achieved via octopamine receptors instead of tyramine receptors. This experiment is helpful to further understand the role of biogenic amines in mating regulation and to provide a new strategy for controlling P. xylostella.

研究领域: 昆虫学 · 神经生物学
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RSC Advances · 2022 ·Vol. 12 ·期 48 ·31497-31505 · IF 4.036

Development of a hematite nanotube and tyramine-based drug carrier against drug-resistant bacteria Klebsiella pneumoniae

M. R. Ali,M. S. Bacchu,D. D. Ridoy,P. L. Mozumder,M. N. Hasan,S. Das,M. F. H. Palash,S. Akter,N. Sakib,A. Khaleque,D. Chakrobortty,M. Z. H. Khan

In this study, hematite nanotube (HNT) and tyramine-based advanced nano-drug carriers were developed for inhibiting the growth of Klebsiella pneumoniae (K. pneumoniae). The HNT was synthesized by following the Teflon line autoclaved assisted hydrothermal process and tyramine was incorporated on the surface of the HNT to fabricate the formulated nano-drug. The nano-drug was prepared by conjugating meropenem (MP) on the surface of Tyramine-HNT and characterized using different techniques, such as scanning electron microscopy (SEM), attenuated total reflection Fourier transform infrared (ATR-FTIR), etc. Furthermore, the drug-loading efficiency and loading capacity were measured using a UV-vis spectrometer. The pH, amount of Tyr, and HNT required for drug loading were optimized. A controlled and gradual manner of pH-sensitive release profiles was found after investigating the release profile of MP from the carrier drug. The antibacterial activity of MP@Tyramine-HNT and MP was compared through the agar disc diffusion method which indicates that antibacterial properties of antibiotics are enhanced after conjugating. Surprisingly, the MP@Tyramine-HNT exhibits a minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of K. pneumoniae lower than MP itself. These results indicate the nanocarrier can reduce the amount of MP dosed to eradicate K. pneumoniae.

CAS / MDL: 51-67-2
研究领域: 材料科学 · 微生物学 · 药学
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Polymer Chemistry · 2014 ·Vol. 5 ·期 17 ·5069-5076 · IF 5.368

Injectable enzymatically crosslinked hydrogels based on a poly(L-glutamic acid) graft copolymer

Kaixuan Ren,Chaoliang He,Yilong Cheng,Gao Li,Xuesi Chen

Enzymatically crosslinked injectable hydrogels based on poly(L-glutamic acid) grafted with tyramine and poly(ethylene glycol) (denoted as PLG-g-TA/PEG) were developed under physiological conditions in the presence of horseradish peroxidase (HRP) and hydrogen peroxide (H2O2). Their gelation time, mechanical properties, swelling behaviors and porous structure were evaluated. The hydrogels were rapidly formed in the presence of low concentrations of HRP and H2O2. The storage modulus of the hydrogels could be well controlled and increased by increasing the concentrations of HRP and H2O2. The average pore-size of the hydrogels varied from 20 to 120 μm, depending on the H2O2 concentration. In addition, the encapsulated L929 fibroblast cells in the PLG-g-TA/PEG hydrogels exhibited high viability. After subcutaneous injection of the PLG-g-TA/PEG solutions containing HRP and H2O2 into the back of rats, the hydrogels were rapidly formed in situ. The hydrogels were found to persist for up to 10 weeks in vivo, and histological analysis indicated that the hydrogels exhibited acceptable biocompatibility. These results suggested that the biocompatible, injectable enzyme-mediated PLG-g-TA/PEG hydrogels are promising for biomedical applications including tissue engineering scaffolds and drug delivery carriers.

研究领域: 生物材料 · 组织工程 · 药物递送
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2024 · IF 5.7

Multicopper Oxidase from Lactobacillus hilgardii: Mechanism of Degradation of Tyramine and Phenylethylamine in Fermented Food

Qilin Yang,Yitao Bai,Shuangping Liu,Xiao Han,Tiantian Liu,Dongna Ma,Jian Mao

Elevated levels of biogenic amines (BAs) in fermented food can have negative effects on both the flavor and health. Mining enzymes that degrade BAs is an effective strategy for controlling their content. The study screened a strain of Lactobacillus hilgardii 1614 from fermented food system that can degrade BAs. The multiple copper oxidase genes LHMCO1614 were successfully mined after the whole genome protein sequences of homologous strains were clustered and followed by homology modeling. The enzyme molecules can interact with BAs to stabilize composite structures for catalytic degradation, as shown by molecular docking results. Ingeniously, the kinetic data showed that purified LHMCO1614 was less sensitive to the substrate inhibition of tyramine and phenylethylamine. The degradation rates of tyramine and phenylethylamine in huangjiu (18% vol) after adding LHMCO1614 were 41.35 and 40.21%, respectively. Furthermore, LHMCO1614 demonstrated universality in degrading tyramine and phenylethylamine present in other fermented foods as well. HS-SPME-GC-MS analysis revealed that, except for aldehydes, the addition of enzyme treatment did not significantly alter the levels of major flavor compounds in enzymatically treated fermented foods (p > 0.05). This study presents an enzymatic approach for regulating tyramine and phenylethylamine levels in fermented foods with potential applications both targeted and universal.

研究领域: 微生物学 · 食品安全 · 酶学
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Polymer Chemistry · 2017 ·Vol. 8 ·期 45 ·7017-7024 · IF 5.375

Enzymatically crosslinked hydrogels based on linear poly(ethylene glycol) polymer: performance and mechanism

Kaixuan Ren,Bin Li,Qinghua Xu,Chunsheng Xiao,Chaoliang He,Gao Li,Xuesi Chen

In the present work, a horseradish peroxidase (HRP)-catalyzed hydrogel based on a double-end tyramine conjugated linear poly(ethylene glycol) (TA-PEG-TA) polymer is developed. The TA-PEG-TA is designed to act as not only a substrate of HRP, but also a macromonomer. We find that, the linear structure is sufficient to form robust hydrogels, and therefore it greatly simplifies the polymer architecture applicable to HRP-catalyzed hydrogels, which are always based on graft or branched polymers. The gelation time and strength of the TA-PEG-TA hydrogels can be well tuned by varying the concentrations of the polymer and HRP as well as the molar ratios of H2O2 to TA groups. The gelation mechanism is clarified by exploring the HRP-catalyzed reaction of a single-end tyramine conjugated poly(ethylene glycol) monomethyl ether (mPEG-TA). The multiple active hydrogen atoms (in the hydroxyl group and the o-position) of phenol moieties can be oxidized by H2O2via HRP catalysis, which should be responsible for the generation of mPEG-TA oligomers and the gelation of TA-PEG-TA. This study provides a new strategy for the design of injectable enzymatically crosslinked hydrogels.

研究领域: 生物材料 · 高分子化学 · 组织工程
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PHYTOCHEMISTRY · 2021 · IF 4.072

Metabolite pattern in root nodules of the actinorhizal plant Casuarina equisetifolia

Yu Jin,Yingting Xu,Zhengwan Huang,Zhongyu Zhou,Xiaoyi Wei

Casuarina equisetifolia L. (Casuarinaceae), an actinorhizal plant , exhibits mutualistic symbiosis with Frankia and promotes nitrogen fixation in root nodules . While the exchange of metabolites between host plant and microsymbiont is well understood in legume symbioses, the situation in the symbiosis between nitrogen-fixing Frankia and actinorhizal plants is less clear. In this study, a metabolomic approach was applied to root nodules of mature C. equisetifolia trees, leading to the identification of an undescribed taraxerane-type triterpenoid ester, 3- O -dihydrocoumaroyl β -taraxerol, along with twelve known compounds. An abundant component was tyramine with a content of 2.76 ± 0.315 mg/g FW in mature nodules. Tyramine specifically and abundantly accumulated in mature nitrogen-fixing nodules compared to senescent nodules, stems, leaves, and seeds. In addition, the potential function of tyramine was preliminarily examined and discussed.

CAS / MDL: 6915-15-7 51-67-2
研究领域: 植物生理学 · 共生关系 · 代谢组学
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TALANTA · 2019 · IF 4.916

Detection of tyramine and tyrosinase activity using red region emission NaGdF4:Yb,Er@NaYF4 upconversion nanoparticles

Huihui Wang,Yunyun Lu,Lun Wang,Hongqi Chen

A selective, simple and environment-friendly type fluorescence sensing platform between upconversion nanoparticles (UCNPs) and melanin-like polymer utilizing the photoinduced electron-transfer (PET) mechanism was developed. The effective fluorescence quenching of UCNPs by melanin-like polymers could detect tyramine and tyrosinase (TYR) activity through the bio-catalysed oxidation of tyramine to the melanin-like polymer products. At optimal conditions, the range of linearity in detection was 0.167–33.3 μΜ for tyramine, and the limit of detection of tyramine was 0.026 μΜ. The linear range of TYR was 0.0033–1 U·mL −1 , and the limit of detection of TYR was 0.003 U·mL −1 . Furthermore, the strategy could be applied to real sample analysis with satisfactory results.

研究领域: 生物化学 · 分析化学 · 纳米医学
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ANALYTICA CHIMICA ACTA · 2024 · IF 5.7

Fluorometric “AND” logic gate for detection of tyramine and tyrosinase based on in-situ formation of silicon-containing nanoparticles

Tingting Wang,Fangning Liu,Chuanxia Chen,Yizhong Lu

Background Tyramine is an important index of food freshness degree, and tyrosinase that can specifically oxidized monophenolamine to catecholamine plays a crucial part in the occurrence and development of melanin-related skin diseases. Therefore, it is crucial to develop sensitive and efficient methods for the detection of tyramine and tyrosinase. Results In this work, encouraged by tyrosinase-triggered specific oxidation of tyramine to dopamine and the unique fluorescent reaction between dopamine and amino silane, we have developed a one-step synthetic strategy of silicon containing nanoparticles (Si CNPs) for “turn-on” detection of tyramine and tyrosinase. The Si CNPs formed with thoroughly studied mechanism exhibit uniform structure and robust yellow-green fluorescence. The low detection limits for tyramine (1.87 μM) and tyrosinase (0.0029 U/mL) demonstrate admirable sensitivity outstripping most methods. The proposed assay achieves satisfactory results in the determination of tyramine and tyrosinase activity in real samples. Furthermore, we leverage this new fluorescent assay to enable the fabrication of an “AND” Boolean logic gate. Significance The entire process can be completed at easily available temperature and pressure with rapid response, convenient operation and visual observation. This fluorescent assay featured with excellent sensitivity, selectivity and stability has considerable prospects in the application of biosensors and disease diagnosis.

研究领域: 生物传感 · 疾病诊断 · 分析化学 · 生物医学工程
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BIOSENSORS & BIOELECTRONICS · 2018 · IF 8.173

Electrochemical detection of tyramine with ITO/APTES/ErGO electrode and its application in real sample analysis

M.Z.H. Khan,Xiaoqiang Liu,J. Zhu,F. Ma,W. Hu,Xiuhua Liu

This work reports the development of a simple and cost-effective electrochemical sensor based on electrochemically reduced graphene oxide (ErGO) bound to the surface of indium tin oxide (ITO) electrode through 3-aminopropyltriethoxysilane (APTES) monolayer (ITO/APTES/ErGO) for selective and sensitive detection of tyramine . The features of the modified electrode were studied by scanning electron microscopy (SEM), cyclic voltammetry (CV), and electrochemical impedance (EIS) methods. The analytical performance of the developed sensor was evaluated with respect to linear detection range, limit of detection, stability, coexistence interference and reproducibility. The modified device exhibited electrocatalytic activity toward tyramine oxidation within two linear concentration range of 1–100 nM, and 1–100 µM, with LOD of 0.1 nM. Finally, the sensor successfully detected tyramine in commercially available real samples with satisfactory recovery ranges. The proposed modified sensor offers distinct advantages including low cost, simple handling, good sensitivity and high selectivity.

研究领域: 分析化学 · 生物医学工程 · 电化学
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