INDUSTRIAL CROPS AND PRODUCTS
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2022
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IF 6.449
Juan He,Lingzhi Song,Zhongkai Wang
The design of functional polyamides for specialized applications has attracted increasing attention during recent years. Herein, a facile and efficient method towards mechanical strong functional polyamides with varied side groups is developed. An α , ω -diene functional amide monomer was prepared through the amidation reaction of methyl 10-undecenoate (a kind of castor oil derivative) and 1,3-diamino-2-propanol. The pendant hydroxyl group was converted to ester groups to afford six other monomers. High molecular weight functional polyamides with varied pendant groups, including hydroxyl, acetate, butyrate , isobutyrate, benzoate, acrylate, and imidazole, were prepared via thiol-ene addition polymerization. Differential scanning calorimetry (DSC) and atomic force microscopy (AFM) results indicate that the melting temperature, degree of crystallization, and crystalline size depend on the pendant groups. Inspired by natural silk proteins , functional polyamides with controllable mechanical properties can be achieved by copolymerizing of these monomers.
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2020
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IF 4.192
Peifei Wang,Songbai Liu
In this study, development of the gemini gallate (GG) interfacial antioxidant for oil in water (O/W) emulsion was performed employing Steglich esterification with gallic acid and dodecyl gemini chains through a prepacked column and peristaltic pump-based purification system. The structural identity and purity of the prepared GG and monogallate (MG) were confirmed by NMR, Fourier transform infrared spectroscopy, and high-performance liquid chromatography–mass spectrometry. Further evaluation revealed that the GG possessed excellent radical scavenging activity and superior antioxidant activity in an O/W emulsion relative to the MG, especially under the condition of a reduced amount of the emulsifier. Microscopic investigation by a fluorescent probe and transmission electron microscopy (TEM) unveiled that the extraordinary antioxidant performance in the O/W emulsion was presumably attributed to preferable interfacial location because of the unique gemini molecular architecture. The superior antioxidant activity of the gemini antioxidant holds great promise for antioxidation in O/W emulsions.
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JOURNAL OF CHROMATOGRAPHY A
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2020
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IF 4.049
Gui-Hua Zhang,Jiang-Bo Xi,Wei Chen,Zheng-Wu Bai
The aim of the present study was to compare the enantioseparation performance of chiral stationary phases (CSPs) which were derived from chitosans of different sources and molecular weights. Therefore, chitosans of shrimp and crab shells were prepared. The viscosity-average molecular weights of the chitosans both prepared from shrimp and crab shells were 2.8 × 10 5 and 1.4 × 10 5 . The chitosans were isobutyrylated yielding isopropylcarbonyl chitosans which were then derivatized with 4-methylphenyl isocyanate to provide chitosan 3,6-bis(4-methylphenylcarbamate)-2-(isobutyrylamide)s. The chitosan 3,6-bis(4-methylphenylcarbamate)-2-(isobutyrylamide)s were used as chiral selectors (CSs) with which the corresponding CSPs were prepared. With the same chiral analytes and under the same mobile phase conditions, the enantioseparation capability of the CSPs was evaluated by high-performance liquid chromatography. In two CSs prepared from the same source, the one with higher molecular weight showed better enantioseparation capability; in two CSs prepared with the chitosans of the same molecular weight, the one derived from shrimp shell exhibited better performance. With regard to the two shrimp chitosan CSs, most of chiral analytes interacted more strongly with the one with lower molecular weight, and an opposite trend was found for the two crab chitosan CSs. Based on the results observed in the present study and in previous work, we believe that the influence of molecular weight on CSP enantioseparation performance is related to the substituent introduced in the CS molecule.
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Advanced Science
·
2021
·Vol. 8
·期 18
·2100950
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IF 16.806
Xiaoli Liu,Yifan Zhang,Yu Guo,Wangbo Jiao,Xiao Gao,Wee Siang Vincent Lee,Yanyun Wang,Xia Deng,Yuan He,Ju Jiao,Ce Zhang,Guoqing Hu,Xing-Jie Liang,Haiming Fan
Effective delivery of anticancer drugs into the nucleus for pharmacological action is impeded by a series of intratumoral transport barriers. Despite the significant potential of magnetic nanovehicles in electromagnetic field (EF)-activated drug delivery, modularizing a tandem magnetoresponsive activity in a one-nanoparticle system to meet different requirements at both tissue and cellular levels remain highly challenging. Herein, a strategy is described by employing sequential EF frequencies in inducing a succession of magnetoresponses in the magnetic nanovehicles that aims to realize cascaded tissue penetration and nuclear accumulation. This nanovehicle features ferrimagnetic vortex-domain iron oxide nanorings coated with a thermo-responsive polyethylenimine copolymer (PI/FVIOs). It is shown that the programmed cascading of low frequency (L f )-EF-induced magnetophoresis and medium frequency (M f )-EF-stimulated magneto-thermia can steer the Doxorubicin (DOX)-PI/FVIOs to the deep tissue and subsequently trigger intracellular burst release of DOX for successful nuclear entry. By programming the order of different EF frequencies, it is demonstrated that first-stage L f -EF and subsequent M f -EF operation enables DOX-PI/FVIOs to effectively deliver 86.2% drug into the nucleus in vivo . This nanodelivery system empowers potent antitumoral activity in various models of intractable tumors, including DOX-resistant MCF-7 breast cancer cells, triple-negative MDA-MB-231 breast cancer cells, and BxPC-3 pancreatic cancer cells with poor permeability.
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2019
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IF 3.571
Shanshan Wang,Kai Ye,Tong Shu,Xiuwen Tang,Xiu Jun Wang,Songbai Liu
In this study, incorporation of gallic acid into typical phytosterols (β-sitosterol and stigmasterol) through Steglich esterification was optimized employing the protection and deprotection strategy. A novel mechanism leading to side esterification was discovered. Complication of the phenolic hydroxyl groups and side reactions were successfully reduced under the optimized conditions. The structural identity and purity of galloyl stigmasterol and galloyl β-sitosterol were confirmed by NMR, FT-IR, and HPLC-MS. Evaluation of galloyl β-sitosterol and galloyl stigmasterol revealed their excellent antioxidant and cholesterol-reducing activities. Significant enhancement of cholesterol-reducing activity by galloylation was unveiled especially for β-sitosterol. Galloyl β-sitosterol had slightly better antioxidant activity at ambient temperature and better cholesterol-reducing activity. Molecular modeling suggested that a subtle difference of galloyl β-sitosterol and galloyl stigmasterol in activities could be attributed to variation of molecular rigidity and conformation. The excellent properties of galloyl β-sitosterol and galloyl stigmasterol suggested their great potential application in the food industry.
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FOOD CHEMISTRY
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2015
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IF 3.391
Shan Hong,Songbai Liu
The reactivity profile of all the hydroxyl groups in (+)-catechin towards acylation and their respective contribution to radical scavenging activity were systematically explored in this work. Selective acylation of the hydroxyls on different rings was carried out employing either a basic or acidic activation strategy. Monoacylation of B ring was achieved effectively with the aid of dimethyltin dichloride. Monoacylation of A ring was accomplished by sequential protection and deprotection of B and C rings. Based on specific acylation of all the individual hydroxyls of (+)-catechins, the structure radical scavenging activity relationship of each hydroxyl of (+)-catechin was established. It was demonstrated that the vicinal phenolic hydroxyls on B ring played the most important role in the ABTS radical scavenging activity and those on A and C rings made a much smaller contribution. This study has laid solid groundwork for further modification of the catechins and improvement of their properties.
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JOURNAL OF CHROMATOGRAPHY A
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2016
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IF 3.926
Sheng Tang,Qin Bin,Wei Chen,Zheng-Wu Bai,Shao-Hua Huang
A series of chitosan bis(methylphenylcarbamate)-(isobutyrylamide) derivatives were synthesized by carbamylating chitosan isobutyrylamide with different methylphenyl isocyanates. Then the prepared chitosan derivatives were coated onto 3-aminopropyl silica particles, resulting in a series of new chiral stationary phases (CSPs) for high-performance liquid chromatography. It was observed that the chiral recognition abilities of these coated-type CSPs depended very much on the substituents on the phenyl moieties of the chitosan derivatives, the eluent composition, as well as the structure of racemates. As a typical example, the eluent tolerance of the prepared CSP with the best enantioseparation ability was investigated in detail, and the results revealed that the CSP exhibited extraordinary solvent tolerance and could still work without significant loss in enantioseparation capability after being flushed with chloroform (100%), ethyl acetate (100%) and even THF/ n -hexane (70/30, v/v), while the traditional coated-type CSPs based on the cellulose and amylose derivatives, such as cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC) and amylose tris(3,5-dimethylphenylcarbamate) (ADMPC), might be dissolved or highly swollen in these eluents. Therefore, the application of the resultant CSPs could address the problem of the dissolution and high swelling of traditional coated-type CSPs in some unusual eluents, broadening the possibility of eluent choice. In addition, a comparison of the prepared CSPs with the well known CDMPC- and ADMPC- based CSPs concerning the chiral recognition ability was also made. Separation performances achieved on the as-prepared CSPs in different eluents were found to be even superior to CDMPC- and ADMPC-based CSPs for the tested chiral compounds. In summary, we could safely draw the conclusion that the CSPs derived from chitosan isobutyrylamide derivatives were capable of excellent chiral recognition ability, and meanwhile possessed satisfactory eluent tolerance in a wider range of solvents.
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NEW JOURNAL OF CHEMISTRY
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2016
·Vol. 40
·期 11
·9657-9665
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IF 3.277
Sheng Tang,Qin Bin,Zi-Wei Feng,Wei Chen,Shao-Hua Huang,Zheng-Wu Bai
The goal of the present study is to systematically investigate the enantioseparation performance and eluent tolerance of chiral stationary phases (CSPs) derived from chitosan bis(halophenylcarbamate)-(isobutyrylamide)s. Hence, N-isobutyrylated chitosan was prepared from completely deacetylated chitosan with a high molecular weight. The N-isobutyrylated chitosan was further derivatized with various halo-substituted phenyl isocyanates, consequently affording a series of chitosan bis(halophenylcarbamate)-(isobutyrylamide)s, which were coated onto 3-aminopropyl silica particles to obtain a class of CSPs. The chiral recognition ability of these CSPs was evaluated with nineteen racemates. It was found that the chitosan bis(halophenylcarbamate)-(isobutyrylamide)s showed powerful enantioseparation performance, and those with 4-chlorophenylcarbamate, 3,4-dichlorophenylcarbamate and 4-trifluoromethoxyphenylcarbamate seemed to exhibit comparable or even more superior enantioseparation ability for the tested racemates in comparison with the well-known derivatives of cellulose and amylose. In addition, the dissolvability and swelling of the prepared chitosan bis(halophenylcarbamate)-(isobutyrylamide)s in organic solvents were discussed in particular. The eluent tolerance of the CSP prepared from chitosan bis(3,4-dichlorophenylcarbamate)-(isobutyrylamide), which exhibited relatively more favorable enantioseparation performance among the prepared CSPs, was investigated. It was observed that the tested CSP could be analyzed with 100% ethyl acetate, 100% chloroform and n-hexane/THF (70/30, volume ratio) without a significant loss of recognition and enantioseparation ability. As a consequence, we can safely draw the conclusion that chitosan bis(halophenylcarbamate)-(isobutyrylamide)s prepared from chitosan with a high molecular weight can show good enantioseparation performance as well as satisfactory eluent tolerance.
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JOURNAL OF CHROMATOGRAPHY A
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2016
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IF 3.926
Sheng Tang,Jian-De Liu,Qin Bin,Ke-Qin Fu,Xiao-Chen Wang,Ying-Bin Luo,Shao-Hua Huang,Zheng-Wu Bai
In order to comprehensively understand the influence of coordination of the substituent at 2-position with those at 3- and 6-positions on the properties of chitosan derivatives, a series of chitosan 3,6-bis(arylcarbamate)-2-(amide)s (CACAs) and the related chiral stationary phases (CSPs) were prepared and reported in the present study. Specifically, chitosan was N -acylated with carboxylic acid anhydrides, and then further derivatized with various aryl isocyanates to afford CACAs, from which a class of coated-type CSPs were prepared. When the substituent introduced on the acyl group at 2-position and those on the phenyl group of the carbamates at 3- and 6-positions were fittingly combined, these prepared CACAs based CSPs would exhibit powerful chiral recognition ability, further resulting in a class of promising chiral separation materials with excellent enantioseparation performance. Meanwhile, these newly developed materials with suitable molecular weight also bear a high tolerability towards organic solvents, even including pure tetrahydrofuran, thus broadening their application in enantiomeric separation.
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JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
·
2025
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IF 3.1
Lin Chen,Han Huang,Xiali Liu,Peijing Zhao,Biao Zhou
A novel oxyphenisatin analogue was identified in a type of jelly candy during routine inspections of food products marketed for weight-loss purposes. Through analysis utilizing ultra-high-performance quadrupole-Orbitrap high-resolution mass spectrometry (UHPLC-Q-Orbitrap-HRMS), the fragment ions at m/z 258 and 195 observed in the MS/MS experiments were found to be consistent with those of 4-Chloro-oxyphenisatin diacetate. It was inferred that the unknown compound is likely a derivative of 4-Chloro-oxyphenisatin diacetate. The candy was separated and purified by column chromatography, and the purified compound was determined to be 96.4 % by high-performance liquid chromatography (HPLC). Subsequently, the structure was confirmed through nuclear magnetic resonance (NMR) spectroscopy. Based on the data, it was concluded that the structure of the unknown compound involved the substitution of two symmetrical acetyl groups in the 4-chloro-oxyphenisatin diacetate molecule with two isobutyl groups. Ultimately, the novel oxyphenisatin analogue was identified as (5-chloro-2-oxoindolin-3,3-ylidene) bis (4,1-phenylbutan-2-yl) diisobutyrate and designated as 4-Chloro-oxyphenisatin diisobutyrate. Finally, a quantitative analysis of the novel unknown compound in the jelly candy revealed a concentration of 6 mg per pellet. Based on the recommended daily consumption of one pellet, as indicated on the product packaging, the level of illegal additives may lead to diarrhoea and consequently poses a risk to human health. To the best of our knowledge, this represents the first report on the identification of 4-Chloro-oxyphenisatin diisobutyrate.
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ACS Applied Materials & Interfaces
·
2024
·
IF 8.3
Xun Wang,Bin Yan,Hugang Li,Jianlan Yuan,Jingyi Guo,Siyao Wang,Penggao Dai,Xiaoli Liu
Indoleamine 2,3-dioxygenase (IDO), highly expressed in hepatocellular carcinoma (HCC), plays a pivotal role in creating an immune-suppressive tumor microenvironment. Inhibiting IDO activity has emerged as a promising immunotherapeutic strategy; however, the delivery of IDO inhibitors to the tumor site is constrained, limiting their therapeutic efficacy. In this study, we developed a magnetic vortex nanodelivery system for the targeted delivery of the IDO inhibitor NLG919, integrated with magnetic hyperthermia therapy to reverse the immune-suppressive microenvironment of liver cancer and inhibit tumor growth. This system comprises thermoresponsive polyethylenimine-coated ferrimagnetic vortex-domain iron oxide nanorings (PI-FVIOs) loaded with NLG919 (NLG919/PI-FVIOs). Under thermal effects, NLG919 can be precisely released from the delivery system, counteracting IDO-mediated immune suppression and synergizing with NLG919/PI-FVIOs-mediated magnetothermodynamic (MTD) therapy-induced immunogenic cell death (ICD), resulting in effective HCC suppression. In vivo studies demonstrate that this combination therapy significantly inhibits tumor growth and metastasis by enhancing the accumulation of cytotoxic T lymphocytes and suppressing regulatory T cells within the tumor. Overall, our findings reveal that NLG919/PI-FVIOs can induce a potent antitumor immune response by disrupting the IDO pathway and activating the ICD, offering a promising therapeutic avenue for HCC treatment.
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FOOD CHEMISTRY
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2025
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IF 9.8
Humera Rani,Songbai Liu
In this study, novel amphiphilic antioxidants, galloyl acylglycerols (GAGs), were successfully synthesized by integrating gallic acid (GA) with acylglycerols of varying acyl chain length (C 12 -C 18 ) using mild Steglich esterification. The structural identities of these derivatives were confirmed through NMR and MS analysis. Further evaluation revealed that GAG-C 18 exhibited excellent radical scavenging activity and superior antioxidant performance in both simple and complex liposomal dispersions compared to other gallic acid derivatives. Additionally, GAG-C 18 effectively minimized the degradation and leakage of bioactives including curcumin and anthocyanins in multilayer and multivesicular liposomes. Microscopic investigation by confocal microscopy further demonstrated the visual results of the GAG-C 18 to protect the liposome under oxidation. As an amphiphilic antioxidant, GAG-C 18 demonstrated increased efficiency in lipid dispersions by preferentially accumulating in the oil-water interface, where oxidation predominantly occurs. The remarkable antioxidant performance of naturally derived amphiphilic GAG antioxidants makes them ideal candidates for ensuring oxidative stability in delivery systems.
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