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MOLECULAR PHARMACEUTICS · 2016 · IF 4.342

Comparison of Two Approaches for the Attachment of a Drug to Gold Nanoparticles and Their Anticancer Activities

Yingjie Fu,Qishuai Feng,Yifan Chen,Yajing Shen,Qihang Su,Yinglei Zhang,Xiang Zhou,Yu Cheng

Drug attachment is important in drug delivery for cancer chemotherapy. The elucidation of the release mechanism and biological behavior of a drug is essential for the design of delivery systems. Here, we used a hydrazone bond or an amide bond to attach an anticancer drug, doxorubicin (Dox), to gold nanoparticles (GNPs) and compared the effects of the chemical bond on the anticancer activities of the resulting Dox-GNPs. The drug release efficiency, cytotoxicity, subcellular distribution, and cell apoptosis of hydrazone-linked HDox-GNPs and amide-linked SDox-GNPs were evaluated in several cancer cells. HDox-GNPs exhibited greater potency for drug delivery via triggered release comediated by acidic pH and glutathione (GSH) than SDox-GNPs triggered by GSH alone. Dox released from HDox-GNPs was released in lysosomes and exerted its drug activity by entering the nuclei. Dox from SDox-GNPs was mainly localized in lysosomes, significantly reducing its efficacy against cancer cells. In addition, in vivo studies in tumor-bearing mice demonstrated that HDox-GNPs and SDox-GNPs both accumulate in tumor tissue. However, only HDox-GNPs enhanced inhibition of subcutaneous tumor growth. This study demonstrates that HDox-GNPs display significant advantages in drug release and antitumor efficacy.

研究领域: 药物递送 · 癌症化学疗法 · 生物医学工程
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JOURNAL OF HAZARDOUS MATERIALS · 2012 · IF 4.173

Modifying Fe3O4 microspheres with rhodamine hydrazide for selective detection and removal of Hg2+ ion in water

Zhuqing Wang,Dayu Wu,Genhua Wu,Ningning Yang,Aiguo Wu

Rhodamine hydrazide modifying Fe 3 O 4 microspheres (Fe 3 O 4 -R6G) was developed for selective detection and removal of mercury ion from water. With a saturation magnetization of 74.2   emu/g, the Fe 3 O 4 -R6G could be simply recollected from water with magnetic separation within a few minutes. The selectivity and adsorption ability of Fe 3 O 4 -R6G for metal cations were studied by fluorophotometry and atomic absorption spectrometry, respectively. The results showed that Fe 3 O 4 -R6G exhibited excellent selectivity for sensing mercury ion over other metal ions in aqueous solution, and also adsorbed 91% of mercury ion. The maximum adsorption capacity of the Fe 3 O 4 -R6G for Hg 2+ ion was 37.4   μmol   g −1 . The Fe 3 O 4 -R6G was successfully applied to the determination of Hg 2+ in environmental samples, and could be used repeatedly by treatment with tetrabutylammonium hydroxide.

CAS / MDL: 107-22-2 2052-49-5
研究领域: 环境科学 · 分析化学
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ANALYTICAL CHEMISTRY · 2017 · IF 6.32

Electrochemical Analysis of Enzyme Based on the Self-Assembly of Lipid Bilayer on an Electrode Surface Mediated by Hydrazone Chemistry

Juan Zhang,Xiaonan Wang,Tingjun Chen,Chang Feng,Genxi Li

In this work, a new strategy for electrochemical analysis of enzyme has been proposed based on a self-assembled lipid bilayer on an electrode surface mediated by hydrazone chemistry. Taking aldolase as an example, the enzyme can catalyze the formation of products containing carbonyl groups. These groups can react with hydrazine groups of the functional lipid derivative, resulting in the self-assembly of a lipid bilayer on a guanidinium modified electrode surface. The lipid bilayer will then prevent the movement of hydrophilic electrochemical probes. Consequently, the catalytic reaction of the enzyme may result in the change of the obtained electrochemical peak current. Experimental results reveal that aldolase activity can be analyzed over a widely linear detection range from 5 mU/L to 100 U/L with a low detection limit of 1 mU/L. Meanwhile, the method can exhibit good precision and reproducibility and it can be applied for real sample analysis. What is more, because the lipid bilayer is the universal basis for cell-membrane structure, while hydrazone chemistry is popular in nature, this work may also provide a new insight for the development of electrochemical analysis and electrochemical biosensors.

研究领域: 生物化学 · 分析化学
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SEPARATION AND PURIFICATION TECHNOLOGY · 2024 · IF 8.1

Layered heterogeneous polyamide-hydrazide based reverse osmosis membranes with enhanced separation performance

Zhongyang Wang,Muhammad Adnan Akram,Lihua Zhao,Zhiyu Liu,Q. Jason Niu

It is the goal of membrane science to continuously overcome the trade-off between permeability and selectivity of reverse osmosis (RO) membranes. In this study we propose a strategy based on the pore characteristics of cyclobutane-1,2,3,4-tetracarboxylic acid chloride (BTC) and trimesoyl chloride (TMC) crosslinked with cyclobutane-1,2,3,4-tetracarbohydrazide (CBTH) for constructing layered heterostructures of polyamide-hydrazide membranes. By using BTC and TMC successively, the porous BTC-CBTH polyamide was employed as the bottom layer, and the dense TMC-CBTH polyamide as the top layer, creating an RO membrane with a “sparse and dense” heterogeneous structure. This layered heterostructure ingeniously differentiates the structure and function of the selective layer of the RO membrane, enabling the loose bottom layer and the dense top layer to respectively perform the tasks of support and separation. The permeability coefficient of the prepared RO membrane reached 3.82 L⋅m −2 ⋅h −1 ⋅bar −1 , which was enhanced by 29% compared with that of the polyamide-hydrazide membrane prepared by single-step interfacial polymerization, while the rejection of NaCl was maintained at 99.13 %. The heterogeneous layered construction strategy effectively improves the permeability and selectivity of the RO membrane, and provides a universal solution for consistently overcoming the “trade-off” effect in RO membranes.

研究领域: 材料科学 · 环境工程
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JOURNAL OF BIOMATERIALS APPLICATIONS · 2019 · IF 2.442

Targeted pharmacokinetics of polymeric micelles modified with glycyrrhetinic acid and hydrazone bond in H22 tumor-bearing mice

Yan Zheng,Shudan Shi,Yaru Liu,Yandan Zhao,Yuqi Sun

Liver cancer is one of the most common malignant tumors. Chemotherapy drugs have been widely used in the anti-hepatoma research. However, low targeting efficiency and serious adverse reaction are their main drawbacks. Liver tumor was proved to have a slightly acidic microenvironment (pH 4.5–5.5) and many glycyrrhetinic-acid-specific binding sites. Therefore, in the present study, the glycyrrhetinic acid- and hydrazone bond-modified micelles were designed. mPEG-HZ-PLA and GA-PEG-PLA copolymer were synthesized to prepare glycyrrhetinic-acid-modified pH-sensitive polymeric micelles (GA-PEG-HZ-PLA). The targeted pharmacokinetics was used to evaluate the effect in hepatoma 22 tumor-bearing mice after the micelles were administered intravenously. The contents of coumarin-6 in blood and tissues were determined through high-performance liquid chromatography using a fluorescence detection (HPLC-FLD) with coumarin-30 as inner standard. The micelles have shown long-circulation effects and two-department models. In the targeting pharmacokinetics, the relative intake efficiency, targeted efficiency, relative targeting efficiency, and concentration ratio of GA-PEG-HZ-PLA in the tumor were 3.24, 4.04, 3.00, and 2.47, respectively. We have demonstrated that GA-PEG-HZ-PLA was more effectively accumulated in the liver and tumor. Thus, the prepared active-targeted and pH-sensitive micelles modified with glycyrrhetinic acid structure and hydrazone bond are promising tools for effective liver cancer therapy.

研究领域: 药学 · 肿瘤学
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TALANTA · 2020 · IF 5.339

Combination of imine bond and samarium emitter enables turn-off fluorescence detection of hydrazine in vapor and water samples

Kun Zhang,Yan Huang,Yin-Jing Shen,Shuang Ma,Ting-Ting Chen

The development of convenient and efficient fluorescence techniques is of great significance for selective detection and precise determination of biotoxic N 2 H 4 in human health and environmental sciences. By the pre-organization-assisted template synthesis , disclosed here is a luminescent Sm(III) macrocycle-based probe Sm - 2 m bearing dynamic imine bonds as recognition moieties which provides the selective and ratiometric turn-off fluorescence sensing for N 2 H 4 over various amine species based on the N 2 H 4 -induced structure transformation. This fluorescent sensing process finished within 20 min shows the low limit of detection (0.18 μM, 7.2 ppb) and wide linear sensing range (0–60.0 μM). Furthermore, probe Sm - 2 m is also be used to quantitatively determine N 2 H 4 in vapor gas and water samples through fluorescence color changes, which are evaluated by the Sm - 2 m -impregnated test paper strips and RGB value outputs. Finally, our proposed smartphone-based analytical method gives satisfactory N 2 H 4 detection results. It is thus believed that this work can shed some lights on development of optical probes and detection techniques for N 2 H 4 , even other hazardous chemicals.

CAS / MDL: 67-64-1
研究领域: 化学 · 环境科学 · 生物医学
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INDUSTRIAL CROPS AND PRODUCTS · 2024 · IF 5.6

A new strategy for efficient detection of triflumuron residues in food: An electrochemical sensor derived from a Cu/Fe-BTC MOF-polymer

Liu Yang,Yu-Han Sun,Xian-Xian Ji,Yuan-Zhen Wang,Yu-Long Liu,Ying Fu,Fei Ye

Triflumuron is an insect growth regulator belonging to the class of insecticides. It finds its primary application in the agricultural sector for the control of various pests, particularly certain beetles, aphids, locusts, and mites. In this paper, a Cu/Fe-BTC composite was synthesized through a straightforward solvothermal approach, subsequently employed as a precursor for the fabrication of an electrochemical sensor denoted as CuFe 2 O 4 @C . The latter exhibited a distinctive core-shell architecture achieved through annealing, and its application was focused on the sensitive detection of triflumuron. The electrochemical behaviour of CuFe 2 O 4 @C for the detection of triflumuron was evaluated by differential pulse voltammetry (DPV) under optimal conditions in wide concentrations from 1.0 × 10 −4 to 1.0 × 10 −12 mol·L −1 , where there existed a superior linear relationship between the current and the concentration of triflumuron with R 2 being 0.995. Meanwhile, CuFe 2 O 4 @C had a low limit of detection (LOD) of 922 fM for triflumuron. The CuFe 2 O 4 @C/GCE exhibited remarkable sensitivity, long-term stability, excellent reproducibility, and repeatability, as well as effective anti-interference capabilities. Additionally, CuFe 2 O 4 @C demonstrated its applicability for the quantitative determination of triflumuron in diverse real samples with commendable recovery rates. In conclusion, the electrochemical sensor not only displayed exceptional performance in terms of stability, reproducibility, and anti-interference, but also showcased its practical utility in quantifying triflumuron across various real-world samples.

研究领域: 农业科学 · 分析化学
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CARBOHYDRATE POLYMERS · 2015 · IF 4.074

Conjugating an anticancer drug onto thiolated hyaluronic acid by acid liable hydrazone linkage for its gelation and dual stimuli-response release

Chaoping Fu,Hailiang Li,Nannan Li,Xiangwan Miao,Minqiang Xie,Wenjun Du,Li-Ming Zhang

A prodrug gelation strategy was developed for the sustained and dual stimuli-response release of doxorubicin hydrochloride (DOX·HCl), a commonly used anticancer drug. For this purpose, the chemical conjugation of DOX·HCl onto thiolated hyaluronic acid (HA) was carried out by an acid liable hydrazone linkage and verified by 1 H NMR analyses. When exposed to the air, such a polysaccharide conjugate showed unique self-gelation ability in aqueous solution. The gelation time and extent depended mainly on the content of thiol groups on thiolated HA. The resultant hydrogel exhibited a dominant elastic response and a thixotropic property. In particular, it could release sustainably conjugated DOX·HCl in dual pH- and reduction-responsive modes. The cumulative drug release was found to be significantly accelerated under the conditions mimicking the intracellular environments of cancer cells. The in vitro cytotoxicity assays for the human nasopharyngeal carcinoma CNE2 cells treated with various release media confirmed the effectiveness of this conjugate hydrogel for cancer cell inhibition.

研究领域: 药剂学 · 肿瘤学 · 生物材料学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2023 · IF 4.4

A pyridine modified naphthol hydrazone Schiff base chemosensor for Al3+ via intramolecular charge transfer process

Brian Musikavanhu,Zeping Huang,Quanhong Ma,Yongdi Liang,Zhaoli Xue,Lei Feng,Long Zhao

A pyridine modified naphthol hydrazone Schiff base chemosensor, NaPy , was prepared in a two-step process to detect aluminum ion (Al 3+ ) in different samples. The probe shows a turn-off emission response towards Al 3+ at a 1:1 binding stoichiometry via intramolecular charge transfer (ICT) mechanism, as validated by density functional theory (DFT) calculations and a series of spectroscopic measurements. The response time is slightly over one minute with a limit of detection (LOD) value of 0.164 µM, demonstrating the great sensitivity of the probe. It is also found that NaPy exhibits high selectivity towards Al 3+ and resists interference from seventeen other cations. Application investigations in paper strips, water samples and HeLa cells suggest that NaPy can be used as an efficient probe for sensing Al 3+ in real environmental samples and biosystems.

研究领域: 分析化学 · 环境科学 · 生物医学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2023 · IF 4.4

Acylhydrazones as sensitive fluorescent sensors for discriminative detection of thorium (IV) from uranyl and lanthanide ions

Hui Xiong,Hua Liang,Ke Dai,Qiang Tian,Xuezhi Dai,Haifeng Su,Guy Royal

Thorium, as a radioactive element, is always associated with rare earth in nature. So it is an exacting challenge to recognize thorium ion (Th 4+ ) in the presence of lanthanide ions because of their overlapping ionic radii. Here three simple acylhydrazones ( AF , AH and ABr , with the functional group fluorine, hydrogen and bromine, respectively) are explored for Th 4+ detection. They all exhibit excellent “turn-on” fluorescence selectivity toward Th 4+ among f-block ions in aqueous medium with outstanding anti-interference abilities, where the coexistence of lanthanide and uranyl ions in addition with other ordinary metal ions have negligible effects during Th 4+ detection. Interestingly, pH variation from 2 to 11 has no significant influence on the detection. Among the three sensors, AF displays the highest sensitivity to Th 4+ and ABr the lowest with the emission wavelengths in the order of λ AF -Th  < λ AH -Th  < λ ABr -Th . The detection limit of AF to Th 4+ can reach 29 nM (pH = 2) with a binding constant of 6.64 × 10 9 M −2 . Response mechanism for AF toward Th 4+ is proposed based on the results of HR-MS, 1 H NMR and FT-IR spectroscopies together with DFT calculations. This work provides important implications on the development of related series of ligands in nuclide ions detection and future separation from lanthanide ions.

研究领域: 分析化学 · 放射化学 · 配位化学
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Journal of Cleaner Production · 2025 · IF 10

Effect of end-capping strategies for regulating multiple-dynamic-bond crosslinked networks on the mechanical self-healing and degradability of vanillin-based waterborne polyurethane

Kuiling Wei,Xuejuan Cao,Yan Wu,Boming Tang,Bailin Shan,Xinqiang Zhang

In recent years, self-healing waterborne polyurethanes (SWPUs) with stimuli-responsive properties have attracted increasing attention. It is critical that dynamic crosslinking networks are designed to respond to appropriate stimulus. In this work, the effects of disulfide bonds, acylhydrazone bonds, and intrinsic hydrogen bonding on the mechanical properties, self-healing performance, and degradation behavior of SWPUs were explored. Initially, disulfide bonds were introduced into the crosslinked networks through a simple chemical modification of cystamine dihydrochloride, providing a cost-effective alternative to typical disulfide bond monomers. Subsequently, bio-based vanillin was used to cap isocyanate groups at ratios of 0.25, 0.5, 0.75, and 1.0, creating reactive sites for the condensation of diacylhydrazine with carbonyl groups. By adjusting the end-capping ratios, varying concentrations of acylhydrazone bonds were incorporated into the networks. The results indicated that increasing the end-capping ratio led to >83.4 % self-healing efficiency of SWPUs under both thermal and acidic conditions. The disordered hydrogen bonds improved the fracture strength of SWPUs, while the ordered hydrogen bonds enhanced the stiffness during stretching. In addition, the degradation test results revealed that SWPU was fully decomposed in a THF solvent (2-mercaptoethanol/deionized water/THF = 2/2/8, volume ratio). This excellent degradability is primarily attributed to the combined effects of imine hydrolysis, dynamic disulfide bonds, and copolymer fragmentation at single bonds near the carbonyl groups. This work presents a novel approach for designing polyurethane elastomers with multiple dynamic adaptive networks, offering the potential for low-cost production and cleaner preparation.

CAS / MDL: 64-19-7
研究领域: 材料科学 · 化学工程
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ACS Applied Polymer Materials · 2024 · IF 4.4

Endowing Polyurethane with Degradability via a Cleavable Bis(cyclohexanone) Oxalyldihydrazone Structure for Adhesive Detachment

Zhengxiang Zhou,Qiangqiang Yan,Yinzhong Guo,Lucy Bai,Tom Kalantar,Amy Song,Wayne Zhang,Yingfeng Yu

Detachable and degradable polymeric adhesives have demonstrated considerable value and significance, accompanying the increasing demands for waste recycling and the ongoing concern for green and sustainable development. Herein, a chain extender containing the bis(cyclohexanone) oxalyldihydrazone structure was introduced into polyurethanes, which achieved efficient degradation in an alkaline environment with the ¯MwMw¯ decreasing from 41.9 to 4.9 kDa. The shear strength of the linear polyurethane between polycarbonate specimens reduced by 98.5%, and on a wide range of substrates, the shear strength of both linear and cross-linked polyurethanes reduced by more than 65.0% as a joint result of the base and cosolvent. These degradable polyurethanes with adhesion properties have exhibited great potential to be used in the separation of multilayer flexible packaging, electronics assembly, and battery pack recycling.

研究领域: 材料科学 · 绿色化学 · 可持续发展
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