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Journal of Materials Chemistry B · 2022 ·Vol. 10 ·期 18 ·3491-3500 · IF 7.571

Self-assembled D-arginine derivatives based on click chemical reactions for intracellular codelivery of antigens and adjuvants for potential immunotherapy

Xiao He,Yannv Qu,Xiaohong Lin,Jiapan Sun,Zhiru Jiang,Chaodong Wang,Yuanfei Deng,Fei Yan,Yansun Sun

Self-assembled amino acid derivatives could form well-defined nanostructures which have great application value for drug delivery systems. In particular, D-amino acid derivatives possess tremendous advantages including anti-degradation and good lysosome escape compared with L-amino acid derivatives. In this work, 9-fluorenylmethyloxycarbonyl (Fmoc) neighboring D-arginine derivatives were replaced by dibenzocyclooctyne (DBCO) to extend the class of functional D-arginine derivatives, which were further reacted with various cross-linkers including azide to construct a library of self-assembled supramolecular nanovehicles and strengthen the stability of nanostructures for disease immunotherapy. Moreover, in vitro studies demonstrated that the combination of DBCO modified D-arginine derivative DR3 and cross-linker C1 not only reinforced the cellular uptake efficiency of ovalbumin (OVA) which was chosen as the model antigen, but also promoted the cytokine TNF-α release of RAW 264.7 cells after the introduction of adjuvant unmethylated cytosine-phosphate-guanine dinucleotides (CpG). Furthermore, the nanovaccine based on DR3C1 could enhance the antigen OVA and adjuvant cytosolic delivery of marrow derived dendritic cells (BMDCs), which improved the antigen-presentation cross efficiency and induced the maturation of BMDCs. Taken together, we believe that D-arginine derivatives functionalized by DBCO provide an effective strategy for disease immunotherapy and act as a great potential delivery tool.

CAS / MDL: 157-06-2
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2022 · IF 5.518

A multifunctional nanocomposite based on Pt-modified black phosphorus nanosheets loading with l-arginine for synergistic gas-sonodynamic cancer therapy

Liang Cheng,Shuilai Qiu,Jing Wang,Weijian Chen,Jingwen Wang,Wenxiang Du,Lei Song,Yuan Hu

Human health is being seriously harmed by tumors. In order to obtain excellent anti-tumor effects, platinum (Pt) nanozyme-modified black phosphorus (BP) loading with L -Arginine (LArg) (BPPL) is prepared to realize nitric oxide (NO) therapy and sonodynamic therapy (SDT), achieving a synergistic effect to therapy. In this system, BP is utilized as the sonosensitizer. Pt can catalyze the decomposition of hydrogen peroxide (H 2 O 2 ) to produce oxygen (O 2 ) and relieve the hypoxic environment of tumor tissue. The increase in O 2 concentration is conducive to the generation of ROS under ultrasound (US) stimulation. The deposition of precious metals hinders the recombination of some electrons (e ) and holes (h + ), and further improves the yield of reactive oxygen species (ROS). LArg is employed as the exogenous NO supplementation. Under the stimulation of US and ROS, NO is generated to cause further cell apoptosis. Tests in vitro and in vivo have proved the great potential of the combination of SDT and gas therapy in tumor treatment.

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Biosensors-Basel · 2023 ·Vol. 13 ·期 5 ·505 · IF 5.4

A Highly Selective Electrochemical Sensor Based on Molecularly Imprinted Copolymer Functionalized with Arginine for the Detection of Chloramphenicol in Honey

Tingrun Lai,Hui Shu,Bo Yao,Siying Lai,Ting Chen,Xuechun Xiao,Yude Wang

Developing an efficient method for chloramphenicol (CAP) detection is of great significance for food safety. Arginine (Arg) was selected as a functional monomer. Benefiting from its excellent electrochemical performance, which is different from traditional functional monomers, it can be combined with CAP to form a highly selective molecularly imprinted polymer (MIP) material. It overcomes the shortcoming of poor MIP sensitivity faced by traditional functional monomers, and achieves high sensitivity detection without compounding other nanomaterials, greatly reducing the preparation difficulty and cost investment of the sensor. The possible binding sites between CAP and Arg molecules were calculated by molecular electrostatic potential (MEP). A low-cost, non-modified MIP electrochemical sensor was developed for the high-performance detection of CAP. The prepared sensor has a wide linear range from 1 × 10−12mol L−1to 5 × 10−4mol L−1, achieves a very low concentration CAP detection, and the detection limit is 1.36 × 10−13mol L−1. It also exhibits excellent selectivity, anti-interference, repeatability, and reproducibility. The detection of CAP in actual honey samples was achieved, which has important practical value in food safety.

CAS / MDL: 13472-35-0 10039-32-4
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2023 · IF 6.1

Molecular Mechanism of ε-Polylysine Treatment of Animal-Derived Foods: Glycine Amidinotransferase Activity Implicates Upregulation of l-Arginine and Creatine

Wei Jia,Jiying Zhu

ε-Polylysine is a novel food preservative approved by the U.S. Food and Drug Administration (FDA), yet the mechanism of its effect on animal-derived foods remains unclear. Assessment of the effect of preservatives on goat meat products is necessary. Herein, metabolite accumulation and protein expression of ε-polylysine (0.025%, w/w) spiked with goat meat were investigated by nontarget metabolomics and proteomics combined with ultrahigh performance liquid chromatography quadrupole-Orbitrap high-resolution-mass spectrometry (UHPLC-Q-Orbitrap HRMS) in a simulated in vitro digestion model. The amino side chain of ε-polylysine increased the activity of glycine aminotransferase due to its nucleophilic nature, inducing a significant upregulation of l-arginine (0.43–0.72 mg kg–1) and creatine (3.98–6.89 mg kg–1), with an improvement in muscle quality of goat meat. Downregulation of enzyme phenylalanine hydroxylase expression led to upregulation of l-phenylalanine (2.26–3.25 mg kg–1) and l-tyrosine (0.98–1.29 mg kg–1). Collectively, this study first revealed the biochemical mechanism of ε-polylysine in goat meat products, which makes available new prospects for more accurate use of ε-polylysine in animal-derived foods.

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CHINESE JOURNAL OF ANALYTICAL CHEMISTRY · 2020 · IF 0.936

A Flexible Electrochemical Sensor Based on L-Arginine Modified Chemical Vapor Deposition Graphene Platform Electrode for Selective Determination of Xanthine

Zhi-Kun BAI,Yi-Tao ZHANG,She-Hong LI,Hong-Xia LUO

A flexible graphene platform electrode (GPE) was prepared by transferring chemical vapor deposition graphene film from Cu foil to polyethylene terephthalate substrate with the help of polymethyl-methacrylate. L -Arginine ( L -Arg) was electrodeposited on GPE to form a poly( L -Arg)/GPE (P( L -Arg)/GPE) which was characterized by scanning electron microscopy, energy dispersive spectroscopy and Raman spectroscopy. The electrocatalytic activity and enhanced conductivity of P( L -Arg)/GPE sensor was evaluated by determining xanthine (XA) in the presence of uric acid (UA) and hypoxanthine (HX) in phosphate buffer solution. The electrochemical behaviors of XA on P( L -Arg)/GPE were studied by cyclic voltammetry and differential pulse voltammetry in comparison with those on bare GPE. The proposed sensor not only achieved the selective determination of XA, but also separated the voltammetric signals of UA and HX with potential differences of 420 and 384 mV, respectively. Under the optimized conditions, the proposed sensor displayed superb sensing property towards XA in a wide linear range of 0.5-140 μmol/L with corresponding detection limit of 0.083 μmol/L ( S/N = 3). With good stability, reproducibility, high sensitivity, low cost as well as high resistance to interferences, the P( L -Arg)/GPE had been applied to determine XA in human serum successfully.

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Materials · 2021 ·Vol. 14 ·期 16 ·4674 · IF 3.623

Development and Characterization of High Efficacy Cell-Penetrating Peptide via Modulation of the Histidine and Arginine Ratio for Gene Therapy

Yu Liu,Huan-Huan Wan,Duo-Mei Tian,Xiao-Jun Xu,Chang-Long Bi,Xiao-Yong Zhan,Bi-Hui Huang,Yun-Sheng Xu,Le-Ping Yan

Cell-penetrating peptides (CPPs), as non-viral gene delivery vectors, are considered with lower immunogenic response, and safer and higher gene capacity than viral systems. In our previous study, a CPP peptide called RALA (arginine rich) presented desirable transfection efficacy and owns a potential clinic use. It is believed that histidine could enhance the endosome escaping ability of CPPs, yet RALA peptide contains only one histidine in each chain. In order to develop novel superior CPPs, by using RALA as a model, we designed a series of peptides named HALA (increased histidine ratio). Both plasmid DNA (pDNA) and siRNA transfection results on three cell lines revealed that the transfection efficacy is better when histidine replacements were on the C-terminal instead of on the N-terminal, and two histidine replacements are superior to three. By investigating the mechanism of endocytosis of the pDNA nanocomplexes, we discovered that there were multiple pathways that led to the process and caveolae played the main role. During the screening, we discovered a novel peptide-HALA2 of high cellular transfection efficacy, which may act as an exciting gene delivery vector for gene therapy. Our findings also bring new insights on the development of novel robust CPPs.Keywords:gene therapy;cell penetrating peptide;histidine;RALA peptide;endosomal escaping

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JOURNAL OF MOLECULAR RECOGNITION · 2017 ·Vol. 31 ·期 1 ·e2657 · IF 2.175

Synthesis, binding ability, and cell cytotoxicity of fluorescent probes for l-arginine detection based on naphthalene derivatives: Experiment and theory

Jie Li,Yang Zhang,Yanmei Chen,Xuefang Shang,Tongyu Ti,Hongli Chen,Tianyun Wang,Jinlian Zhang,Xiufang Xu

Inspired by biological related parts, Schiff base derivatives and functional groups of chemical modification can provide efficient detection method of amino acids. Therefore, we have designed and prepared 4 compounds based on Schiff base derivatives involving ─NO 2 , ─OH, and naphthyl group. Results indicated that compound 4 containing 2 nitro groups showed strong sensitivity and high selectivity for arginine (Arg) among normal 18 kinds of standard amino acids (alanine, valine, leucine, isoleucine, methionine, aspartic acid, glutamic acid, arginine, glycine, serine, asparagine, phenylalanine, histidine, tryptophan, proline, lysine, glutamine, and cysteine). Theoretical investigation also approved the strong binding ability of compound 4 for Arg. In addition, compound 4 displayed high combining ability of Arg and low cytotoxicity of MCF-7 cell in the 0 to 150 μg mL −1 of concentration range; it can be used for Arg in vivo detection of fluorescent probe.

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NEW JOURNAL OF CHEMISTRY · 2017 ·Vol. 41 ·期 24 ·15216-15228 · IF 3.269

A novel carbon dots derived from reduced L-glutathione as fluorescent probe for the detection of the L-/D-arginine

Xiaoqing Zeng,Lei Zhang,Jidong Yang,Yuan Guo,Yunmei Huang,Haiyan Yuan,Yongsheng Xie

In this report, water-soluble carbon dots (CDs) with stable fluorescence (FL) were designed and synthesized by using environment-friendly reduced L-glutathione (GSH) as the precursor and ethylenediamine (EDA) as the passivating agent through a one-step hydro-thermal method. The CDs, with bright blue FL, had the quantum yield (QY) of 40% and showed excellent monodispersity and solubility in water. The FL intensity was remarkably enhanced when a racemic modification of L-/D-arginine (Arg) was added into the CDs solution. Therefore, the CDs could be considered as a sensitive probe for the detection of Arg. Under optimized conditions, the CDs exhibited a linear fluorescence response in the range of 3–124 μM (R2 = 0.9987) Arg with the detection limit of 2.85 × 10−8 M. In addition, no evident difference was observed when comparing the FL results of L-Arg and D-Arg. Therefore, this method could not be used in the chiral recognition of two enantiomers. Under optimum conditions, the mechanism and the reasons for the enhancement of FL were investigated. The developed method exhibited great stability, selectivity and accuracy in determining the Arg content in human urine sample and the recovery range was from 97.0% to 102.2%. Thus, our proposed method has potential application in biological molecular recognition.

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RSC Advances · 2020 ·Vol. 10 ·期 35 ·20886-20899 · IF 3.119

Preparation, characterization and evaluation of a new film based on chitosan, arginine and gold nanoparticle derivatives for wound-healing efficacy

Kai Wang,Zhiping Qi,Su Pan,Shuang Zheng,Haosheng Wang,YuXin Chang,Hongru Li,Pan Xue,Xiaoyu Yang,Chuan Fu

It is well-known that the combination of polymers and nanoparticles (NPs) provides optimised wound dressing and accelerates wound healing. The knowledge about the structure and properties of these materials is of critical importance in biological processes related to wound healing. In this study, we prepared a chitosan (CS) film modified with arginine (Arg) and gold NPs (AuNPs) and investigated its effectiveness as a dressing material for wound healing. Fourier-transform infrared spectroscopy (FTIR) confirmed that Arg was successfully grafted on CS. The resultant CS-Arg/AuNP film was then characterised by transmission electron microscopy (TEM) and scanning electron microscopy (SEM). The modification of Arg and AuNPs improved the hydrophilicity, mechanical strength and antibacterial properties of the film, which in turn provided an enhanced ideal environment for cell adhesion and proliferation. Cell Counting Kit-8 (CCK-8) was used to demonstrate the survival rate. Furthermore, the proteins involved in wound healing were evaluated qualitatively and quantitatively by immunofluorescence and western blotting, respectively. The skin defect models used for the in vivo studies revealed that the CS-Arg/AuNP dressing accelerated wound closure, re-epithelialization and collagen deposition. Our cumulative findings support the feasibility of using the proposed film as a promising candidate for tissue engineering of the skin in the near future.

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Small · 2024 · IF 13

Tumor-Specific Nano-Herb Delivery System with High L-Arginine Loading for Synergistic Chemo and Gas Therapy against Cervical Cancer

Lihua Chen,Hui Ming,Bowen Li,Chen Yang,Shanshan Liu,Yajie Gao,Tingting Zhang,Canhua Huang,Tingyuan Lang,Zhuo Yang

Cancer metastasis poses significant challenges in current clinical therapy. Osthole (OST) has demonstrated efficacy in treating cervical cancer and inhibiting metastasis. Despite these positive results, its limited solubility, poor oral absorption, low bioavailability, and photosensitivity hinder its clinical application. To address this limitation, a glutathione (GSH)-responded nano-herb delivery system (HA/MOS@OST&L-Arg nanoparticles, HMOA NPs) is devised for the targeted delivery of OST with cascade-activatable nitric oxide (NO) release. The HMOA NPs system is engineered utilizing enhanced permeability and retention (EPR) effects and active targeting mediated by hyaluronic acid (HA) binding to glycoprotein CD44. The cargoes, including OST and L-Arginine (L-Arg), are released rapidly due to the degradation of GSH-responsive mesoporous organic silica (MOS). Then abundant reactive oxygen species (ROS) are produced from OST in the presence of high concentrations of NAD(P)H quinone oxidoreductase 1 (NQO1), resulting in the generation of NO and subsequently highly toxic peroxynitrite (ONOO − ) by catalyzing guanidine groups of L-Arg. These ROS, NO, and ONOO − molecules have a direct impact on mitochondrial function by reducing mitochondrial membrane potential and inhibiting adenosine triphosphate (ATP) production, thereby promoting increased apoptosis and inhibiting metastasis. Overall, the results indicated that HMOA NPs has great potential as a promising alternative for the clinical treatment of cervical cancer.

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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2025 · IF 5.4

Synergistic enhancement of surface deposition and moisturizing performance of trehalose and N2-(2,3-dihydroxypropyl)arginine hydrochloride through hydrogen bonding interactions

Bingqing Wang,Haofeng Sun,Jun Gao,Liying Kang,Haixiao Wan,Ying Wu,Hui Ma,Ziling Teng,Xian Xu,Lin Geng,Xiaozhi Wang,Li Ye,Yan Huang,Dongcui Li,Naisheng Jiang

Effective moisturizing agents are crucial for improving the performance of rinse-off cosmetic formulations. Herein, we explored the synergistic effects of trehalose and N 2 -(2,3-dihydroxypropyl)arginine hydrochloride (DPAH), a glycerol derivative of L-arginine, on enhancing surface deposition and moisturizing performance. Using various surface-sensitive characterization techniques, we observed significant enhancements in the surface deposition of the trehalose/DPAH mixture compared to trehalose alone or glycerol-based controls. Molecular dynamics simulations further revealed strong intermolecular hydrogen bonds between trehalose and DPAH, contributing to the observed synergistic effects. A moisture-retention study using a model anionic surfactant-based system demonstrated that the trehalose/DPAH mixture achieves higher skin hydration levels and reduced transepidermal water loss compared to trehalose and DPAH alone. These findings offer new insights into the molecular interactions that enhance the surface deposition and moisturizing efficacy of trehalose, presenting promising opportunities for developing advanced cosmetic formulations with optimized moisture-retaining properties.

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FOOD CHEMISTRY · 2025 · IF 9.8

Physicochemical and rheological properties of konjac glucomannan and its mixed gels with κ-carrageenan: Effect of deacetylation by L-arginine

Ting Zhuo,Jun-ru Qi,Jin-song Liao,Hui-ying Wei,Rong Xiao

Konjac glucomannan (KGM) is a natural functional polysaccharide, and deacetylation (removing acetyl groups) impacts its physicochemical and gel properties. In order to study KGM's gel properties and explore new deacetylation modifiers, three deacetylated konjac glucomannan (DKGM) with different deacetylation degrees (DD, 17.51 %, 35.41 %, and 54.52 %) were prepared using L-arginine. Results showed that L-arginine deacetylated and retained the main structure and high molecular weight of KGM. Solubility decreased from 85.38 % to 81.17 %, transparency decreased from 38.52 % to 35.73 %, water absorbing and swelling slowed down, and molecular morphology changed from chain structures to micelle-like aggregates after deacetylation. Dynamic viscoelastic analysis showed that deacetylation facilitated the formation of the entangled network structure of KGM. The strength of konjac glucomannan and κ-carrageenan mixed gels increased after deacetylation, and this enhancement was mainly through hydrogen bonds and hydrophobic interactions. These findings will provide theoretical guidance for the application of KGM.

CAS / MDL: 11114-20-8 7447-40-7
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