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Cell Death & Disease · 2024 ·Vol. 15 ·期 11 ·1-10 · IF 8.1

Amantadine against glioma via ROS-mediated apoptosis and autophagy arrest

Luo Yusong,Liu Ruolan,Zhang He,Wang Hongyu,Yin Hang,Tian Guopeng,Wang Bo,Yan Yunji,Ding Zilin,Dai Junqiang,Niu Liang,Yuan Guoqiang,Pan Yawen

Glioma is a common primary nervous system malignant tumor with poor overall cure rate and low survival rate, yet successful treatment still remains a challenge. Here, we demonstrated that amantadine (AMT) exhibits the powerful anti-glioma effect by promoting apoptosis and autophagy in vivo and in vitro. Mechanistically, amantadine induces a large amount of reactive oxygen species (ROS) accumulation in glioma cells, and then triggers apoptosis by destroying mitochondria. In addition, amantadine induces the initiation of autophagy and inhibits the fusion of autophagosome and lysosome, consequently performing an anti-glioma role. Taken together, our findings suggest that amantadine could be a promising anti-glioma drug that inhibits glioma cells by inducing apoptosis and autophagy, which may provide a novel potential treatment option for patients.

CAS / MDL: 768-94-5
研究领域: 肿瘤学 · 神经科学 · 药理学
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Nanoscale · 2017 ·Vol. 9 ·期 42 ·16375-16385 · IF 7.367

Superstructures with diverse morphologies and highly ordered fullerene C60 arrays from 1 : 1 and 2 : 1 adamantane–C60 hybrid molecules

Shengju Zhou,Lin Wang,Mengjun Chen,Baoyong Liu,Xiaofeng Sun,Meirong Cai,Hongguang Li

Superstructures from fullerene C60-containing compounds, especially those tethered to rigid functional groups with defined shapes, remain largely unexplored. Being the smallest diamondoid, adamantane (Ad) can be viewed as a promising building block for the construction of well-defined superstructures. Here, we report the syntheses of 1 : 1 (4a) and 2 : 1 (4b) Ad-C60 hybrid molecules, which were then used to construct superstructures in binary solvent mixtures via a modified liquid/liquid interfacial precipitation (LLIP) method using CHCl3 as a good solvent. Typically in the combination of DMSO/CHCl3 with a final concentration (cf) of 1.0 mmol L−1, 4a successively forms spheres, plates, nanoflowers and plicated particles with increasing content of DMSO while 4b forms cuboid blocks and microparticles with hierarchically organized surfaces. Changing from DMSO to other poor solvents including acetone, MeOH and EtOAc leads to variations of the morphology of the superstructures for both 4a and 4b. At the nanometer length scale, 4a and 4b adopt different organizations within the superstructures. While 4a tends to self-organize into lamellae with highly ordered C60 layers, the hexagonal phase is dominant in the superstructures formed by 4b. Wettability tests indicate that films formed by the superstructures of 4a and 4b show anti-wetting properties. Besides the solvent effect, the morphology of the superstructures can be also tuned by concentration. For example, when cf is lowered to 0.5 mmol L−1, a new form of superstructure, i.e., fibers, was detected for 4a. Our results also indicate that besides the solvent-induced aggregate transition, gravity-induced sedimentation and subsequent structure ripening can have a significant influence on the final morphology of the superstructures and the aggregate transition pathways.

研究领域: 材料化学 · 纳米科学
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Materials · 2019 ·Vol. 12 ·期 10 ·1610 · IF 2.972

Nano-Carriers Based on pH-Sensitive Star-Shaped Copolymers for Drug-Controlled Release

Wenzhao Jiang,Jianwei Guo,Weiqiu Wen,Yong-Guang Jia,Sa Liu

Polymeric nano-carriers are considered as promising tools in biomedical applications due to multiple attractive characteristics including their low toxicity, high loading capacity, controlled drug release capabilities, and highly tunable chemical properties. Here, a series of pH-sensitive star-shaped copolymers, Ad-P[(EMA-co-MAA)-b-PPEGMA]4, was prepared via electron transfer atom radical polymerization (ARGETE ATRP) and selective hydrolysis. These star-shaped copolymers can be self-assembled into micelles (Dh= 150–160 nm) and their critical micelle concentrations (CMC) were estimated to be 3.9–5.0 mg/L. The pH-sensitiveness of the micelles was evidenced by transmission electron microscopy (TEM) and dynamic light scattering (DLS). The maximal paclitaxel (PTX) loading efficiency (DLC) and entrapment efficiency (EE) were 18.9% and 36%, respectively. In vitro release studies revealed that about 19% of the PTX released at an acidic condition of pH 1.2 over 70 h, whereas more than 70% was released within the same time interval at pH 6.8. In vitro cytotoxicity suggested that the low cytotoxicity of the blank micelles, while the PTX-loaded micelles providing the cytotoxicity close to that of free PTX. These results indicated that this novel pH-sensitive nano-carriers have great potential applications for oral drug-controlled release.Keywords:nano-carrier;pH-sensitive copolymer;drug release;adamantane

研究领域: 药剂学 · 高分子化学 · 生物医学工程
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CHINESE CHEMICAL LETTERS · 2012 · IF 0.978

Synthesis of novel quaternary ammonium surfactants containing adamantane

Jian Wei Guo,Xing Zhong,Hua Zhu,Li Juan Feng,Ying De Cui

A series of novel quaternary ammonium surfactants containing adamantane were designed and synthesized from 1-adamantanecarboxylic acid. The structures of target surfactants were confirmed by 1 H NMR, elements analysis and FTIR. Surface properties of these surfactants were investigated. Due to the lipophilicity of adamantane, the critical micelle concentration (CMC) and C 20 values of the synthesized quaternary ammonium surfactants are lower than that of conventional quaternary ammonium surfactants.

CAS / MDL: 1119-94-4
研究领域: 化学 · 材料科学
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FUEL · 2019 · IF 5.128

Synthesis and thermal stability of dimethyl adamantanes as high-density and high-thermal-stability fuels

Jiawei Xie,Tinghao Jia,Si Gong,Ning Liu,Genkuo Nie,Lun Pan,Xiangwen Zhang,Ji-Jun Zou

Alkyl-adamantane fuels are appealing for aerospace vehicles due to their high density, good low-temperature performance and thermal stability. Here we reported a facile route to synthesize dimethyl-adamantane fuels via solvent-free rearrangement. The thermodynamic preference of six products (dimethyl-adamantane isomers) was revealed by Density Functional Theory (DFT) calculation and experiment, and the reaction pathway was further discussed. The reaction conditions including catalyst, catalyst dosage, temperature, and solvent were optimized, with the dimethyl-adamantane yield of 88.7%. We synthesized two typical dimethyl-adamantane fuels (with different compositions of isomers) by adjusting the reaction conditions and then evaluated their properties. It is found the two fuels show different fuel properties ( e.g. , density, heating value, thermal stability) due to the difference in methyl substitution position, although both with high density and good low-temperature fluidity. Specifically, the dimethyl-adamantane with methyl on the tertiary carbon shows better thermal stability than JP-10 and decalin. This work presents dimethyl-adamantanes as good high-density and high-thermal-stability fuels, and suggests the position of methyl substitution on adamantane has considerable effect on their properties.

CAS / MDL: 7446-70-0
研究领域: 燃料化学 · 材料科学
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Chemosensors · 2022 ·Vol. 10 ·期 11 ·457 · IF 4.229

Adamantane Three-Dimensional Porous Organic Framework as a Fluorescence Sensor for Rapid Determination of Tetracycline in Aquatic Products

Zhenyu Lu,Yufei Hu,Gongke Li,Ling Xia

A fluorescence adamantane three-dimensional porous organic framework (AdaPOF) was synthesized via a Suzuki coupling reaction. The AdaPOF showed excellent fluorescence performance with a relative high quantum yield and fluorescence stability. Due to its excellent selectivity to tetracycline (TC), a fluorescence sensor based on AdaPOF was constructed for TC determination. The selective sensing mechanism of the AdaPOF towards TC was studied by density functional theory (DFT) calculation experiments. An AdaPOF–based fluorescence method for TC determination was established, with the linear range of 0.1–9.0 μmol/L (R2= 0.9959) and the limit of detection (S/N= 3) of 43 nmol/L. Moreover, the fluorescence method was used to the determination of TC in aquatic products and the recoveries were ranged from 94.4% to 103.8%. The results obtained by this fluorescence method were consistent with those of the high-performance liquid chromatography (HPLC) method in the TC determination.Keywords:adamantane;porous organic framework;tetracycline;fluorescence sensor;aquatic products

研究领域: 分析化学 · 食品科学
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FUEL PROCESSING TECHNOLOGY · 2023 · IF 7.5

Synthesis and fuel properties of high-density and low-freezing-point asymmetric cycloalkyl adamantane

Jiawei Xie,Haodong Zhang,Tinghao Jia,Junjian Xie,Ji-Jun Zou

The exploration to increase the fuel energy density is stimulated by the payload and cruising range concerns in aerospace industry. The high-density fuels are always rationally designed for the advanced volume-limited aircrafts to fulfill more complicated missions. Alkyl adamantanes gradually become a prospective class of high-energy-density fuels. Herein, in this work, we reported an approach to synthesize asymmetric cyclopentyl adamantane via AlCl 3 -catalyzed alkylation of adamantane and cyclopentene with an attractive combination of a high density of 0.990 g/mL as well as a low freezing point of −30 °C. The obtained 1-cyclopentyl-adamantane was well designed with the cyclic substituent (enhance the density) and asymmetric structure (lower the freezing temperature). Subsequently, the comprehensive fuel performance of cyclopentyl adamantane, i.e. , density, freezing point, low-temperature viscosity, heating value , and combustion properties were evaluated. It was shown that both density and combustion properties of cycloalkyl adamantane were superior to the typical high-density JP-10 fuel. In addition, the properties of binary fuel mixture (1-cyclopentyl-adamantane and JP-10) demonstrated that cyclopentyl adamantane could be used as a promising blendstock with conventional jet fuel to enhance the energy density and promote the combustion performance of the final fuel blends.

研究领域: 化学工程 · 能源科学
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POLYMER INTERNATIONAL · 2019 ·Vol. 68 ·期 6 ·1102-1112 · IF 2.433

An injectable and self-healing novel chitosan hydrogel with low adamantane substitution degree

Cheng Liu,Liquan Yang,Liyuan Qiao,Chengde Liu,Manxia Zhang,Xigao Jian

Chitosan (CS) is a semi-natural polymer with supreme biological function, while the strong interchain hydrogen bonds cause poor water solubility and limit its broader use. To break the semi-rigid structure of CS, a kind of CS modified by adamantane (AD-CS) was successfully synthesized by amidation reaction with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride as catalyst. The chemical structure of AD-CS was characterized by Fourier transform infrared spectroscopy and 1 H NMR. The AD substitution degree of CS is around 2%, calculated by 1 H NMR. A soft and transparent hydrogel composed of hydrogen bonds was obtained directly by simply adding a certain amount of water under mild conditions. Rheological measurements were carried out to research the mechanism of hydrogel formation by measuring the influence of different additives and conditions on the AD-CS hydrogel. Reinforced hydrogels were prepared by freezing and thawing. The mechanical strength and self-healing property of reinforced and pristine hydrogels were assessed with an oscillatory rheometer. The modulus of the reinforced hydrogel was obviously enhanced without much loss of self-healing property. Other properties such as adhesion, injectability and temperature response were also studied. These injectable and self-healing hydrogels show potential value in medical care. Additionally, this is a new method to design CS hydrogels with their original interchain hydrogen bonds. © 2019 Society of Chemical Industry

研究领域: 生物材料 · 医学工程
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POLYMER · 2022 · IF 4.432

Adamantane-based block poly(arylene ether sulfone)s as anion exchange membranes

Zhen Wang,Shu Feng Zhou,Yi Zhi Zhuo,Ao Nan Lai,You Zhong Lu,Xiao Bin Wu

Current anion exchange membranes (AEMs) for fuel cells suffer from low ionic conductivity and poor mechanical property. Herein, we introduce adamantane groups onto the block poly(arylene ether sulfone)s backbone to form the selected comb-shaped structure. The structure-property relationships of the AEMs are investigated by varying the ratio of the hydrophobic to hydrophilic segments. The bulk rigid adamantane group can restrain the swelling of the AEMs thus enhancing the mechanical properties and expand the spacing between the hydrophilic/hydrophobic segments of the polymer chains to promote the formation of microphase separation morphology. Consequently, as characterized by atomic force microscope (AFM) and transmission electron microscopy (TEM), the resulting membranes show well-defined microphase separation between the hydrophilic/hydrophobic segments, resulting in high ionic conductivity range from 27.4 to 90.2 mS cm −1 over a temperature range of 30–80 °C. At the same time, the membranes present ultralow swelling ratio with the levels from 1.6% to 6.1% at 30 °C and from 6.8% to 12.7% at 80 °C, respectively, and thus excellent mechanical properties with the tensile strength as high as 11.52 MPa and elongation at break of 29.28%. The excellent comprehensive properties grant the prepared AEMs bright future for fuel cells.

研究领域: 材料科学 · 化学工程
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2022 · IF 5.518

Optical and thermal properties of polymethyl methacrylate (PMMA) bearing phenyl and adamantyl substituents

Weilong Wu,Qin Ouyang,Liu He,Qing Huang

Polymethyl methacrylate (PMMA) is a widely used optical polymer due to its excellent transparency and durability. However, the sole methyl group shows pure PMMA low refractive index and low UV absorbility, and poor thermal stability. In this work, two comonomers phenyl methacrylate (PhMA) and adamantyl methacrylate (AdMA) were used for copolymerization with methyl methacrylate (MMA), and three copolymers P(AdMA-co-MMA), P(PhMA-co-MMA) and P(AdMA-co-PhMA-co-MMA) were prepared. They were characterised by FTIR , 1 H NMR, UV-Vis, ellipsometer , DSC , TG , and TG-MS, and the effects of phenyl and adamantyl substituents on the optical and thermal properties of PMMA were studied. It was found that phenyl played an important role in increasing the absorption and refraction of PMMA in the deep UV region (190–260 nm), while the glass transition temperature and thermal stability of PMMA were more affected by adamantyl than by phenyl. Introduction of phenyl and adamantyl substituents provided a method to tune the optical and thermal properties of PMMA as photoresist or antireflective coating for deep UV lithography.

CAS / MDL: 107-98-2 108-65-6
研究领域: 材料科学 · 高分子化学
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JOURNAL OF PHYSICAL CHEMISTRY B · 2011 · IF 3.603

Responsive Small Molecular Hydrogels Based on Adamantane–Peptides for Cell Culture

Cuihong Yang,Dongxia Li,Zheng Liu,Ge Hong,Jun Zhang,Deling Kong,Zhimou Yang

The development of responsive small molecular hydrogels that can be applied for recovery of cells postculture attract extensive interests for researchers in fields of cell biology, stem cell differentiation, and tissue engineering. We report in this study several responsive small molecular hydrogels based on adamantane–peptides whose gel to clear solution phase transition can be achieved by addition of β-cyclodextrin (β-CD) derivatives. The small molecular hydrogels are formed by our recently developed method of disulfide bond cleavage by glutathione (GSH). Mouse fibroblast 3T3 cells attach and grow well at the surface of hydrogels. Furthermore, 3T3 cells postculture can be recovered from the gels by the addition of a β-CD derivative due to formation of clear solutions by the adamantane−β-CD interaction. The culture on hydrogels and recovery process do not cause obvious effects on behaviors of 3T3 cells. The results shown in this study indicate that small molecular hydrogels based on adamantane–peptides have great potentials in research fields where further analysis of cells is needed.

研究领域: 细胞生物学 · 组织工程 · 干细胞研究
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2016 · IF 2.567

Potential of a β-Cyclodextrin/Adamantane Modified Copolymer in Enhancing Oil Recovery through Host–Guest Interactions

Wan-Fen Pu,Yang Yang,Bing Wei,Cheng-Dong Yuan

In this work, a novel enhanced oil recovery (EOR) copolymer, which is expected to be an alternative to currently used polymers, was successfully synthesized through free radical micellar copolymerization of acrylamide, acrylic acid, 6-acrylamide-β-cyclodextrin (N-β-CD), and acrylamide-adamantane (N-ADA). The copolymer was characterized by Fourier transform infrared spectroscopy, 1H nuclear magnetic resonance spectroscopy, thermal gravimetric analysis, and scanning electron microscopy. The results demonstrated that because of the incorporation of ADA and β-CD groups, host–guest interactions occurred in the aqueous solution, which subsequently improved the salt tolerance, temperature resistance, shear resistance, and viscoelastic properties of the synthesized polymer. Regarding the EOR performance, it was observed that 8.58% incremental oil was produced using this polymer after water flooding was exhausted. The superior properties make this novel polymer promising in enhancing oil recovery, particularly for reservoirs which have discarded polymer flooding techniques because of harsh conditions.

CAS / MDL: 814-68-6 768-94-5
研究领域: 石油工程 · 高分子化学
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