NEW JOURNAL OF CHEMISTRY
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2022
·Vol. 46
·期 9
·4198-4211
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IF 3.925
Na Liu,Juan Teng,Alula Yohannes,Hang Song,Shun Yao
For the extraction of theophylline from a water phase, four hydrophobic ionic liquids (ILs) were designed and synthesized which included various amino acid ester cations and the same bis(trifluoromethyl)sulfonimide anion. After screening, L-phenylalanine ethyl ester bis(trifluoromethyl)sulfonimide ([PheC2][Tf2N]) showed the highest distribution coefficient and it was then applied to further investigations focused on the extraction conditions. It was also immobilized through a simple procedure and used for the adsorption of theophylline for comparison. The new sorbent was characterized via infrared spectroscopy (IR), scanning electron microscopy (SEM), elemental analysis, thermogravimetric analysis, and particle size analysis. In addition, thorough investigations into the adsorption conditions, kinetics, isotherms, and thermodynamics were carried out, together with selective separation studies. The post-treatment and reuse of the IL were also explored using the two separation approaches. A comprehensive comparison was made between these approaches and reported methods.
研究领域:
化学
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药学
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DOI
高影响因子
Drug Design Development and Therapy
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2019
·
IF 3.208
Yan Yan,Pengchong Wang,Ruiying Li,Ying Sun,Rui Zhang,Chuanchuan Huo,Jianfeng Xing,Yalin Dong
Purpose Budesonide (Bud) is a nonhalogenated glucocorticoid with high anti-inflammatory potency and low systemic side effects. However, the poor water solubility of Bud affects its dissolution and release behavior, thus influencing its anti-inflammatory effect. This study was aimed at synthesizing and evaluating novel conjugates of Bud, hoping to increase the anti-inflammatory activity of Bud by improving its water solubility.Materials and methods Seven novel Bud conjugates (3a–3g) were designed and synthesized in this study. Besides, the equilibrium solubility, cell viability, in vitro and in vivo anti-inflammatory activity, and the hydrolysis behavior of the conjugates in different pH solutions, rat and human plasma, and rat lung homogenate were studied in detail.Results As compared to Bud, the equilibrium solubility of 3a, 3c, and 3e was significantly increased; 3a, 3b, and 3c significantly inhibited the interleukin-6 production in lipopolysaccharide-induced A549 cells; 3a and 3e could significantly decrease the xylene-induced ear edema; and 3a and 3c were gradually and slowly hydrolyzed into Bud in the alveolar fluid and lung homogenate and broken down quickly in plasma.Conclusion The amino acid ester compounds budesonide-21-glycine ester (3a) and budesonide-21-alanine ester (3c) were selected as potential conjugates of Bud. This study would provide a theoretical and an experimental basis for the in vivo process of glucocorticoids and the treatment of inflammatory diseases.
研究领域:
药理学
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药物化学
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炎症研究
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产品关联
DOI
PubMed
高影响因子
Catalysts
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2020
·Vol. 10
·期 4
·432
·
IF 3.52
Li-Hua Du,Rui-Jie Long,Miao Xue,Ping-Feng Chen,Meng-Jie Yang,Xi-Ping Luo
A continuous-flow procedure for the synthesis of β-amino acid esters has been developed via lipase-catalyzed Michael reaction of various aromatic amines with acrylates. Lipase TL IM fromThermomyces lanuginosuswas first used to catalyze Michael addition reaction of aromatic amines. Compared with other methods, the salient features of this work include green reaction conditions (methanol as reaction medium), short residence time (30 min), readily available catalyst and a reaction process that is easy to control. This enzymatic synthesis of β-amino acid esters performed in continuous-flow microreactors is an innovation that provides a new strategy for the fast biotransformation of β-amino acid esters.Keywords:enzymatic synthesis;β-amino acid esters;microreactor;aromatic amines;Michael addition
研究领域:
生物化学
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有机化学
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产品关联
DOI
高影响因子
Scientific Reports
·
2016
·Vol. 6
·期 1
·1-9
·
IF 5.228
Xue Shan-Shan,Zhao Meng,Ke Zhuo-Feng,Cheng Bei-Chen,Su Hua,Cao Qian,Cao Zhen-Kun,Wang Jun,Ji Liang-Nian,Mao Zong-Wan
It is challenging to create artificial catalysts that approach enzymes with regard to catalytic efficiency and selectivity. The enantioselective catalysis ranks the privileged characteristic of enzymatic transformations. Here, we report two pyridine-linked bis(β-cyclodextrin) (bisCD) copper(II) complexes that enantioselectively hydrolyse chiral esters. Hydrolytic kinetic resolution of three pairs of amino acid ester enantiomers (S 1 –S 3 ) at neutral pH indicated that the “back-to-back” bisCD complex CuL 1 favoured higher catalytic efficiency and more pronounced enantioselectivity than the “face-to-face” complex CuL 2 . The best enantioselectivity was observed for N -Boc-phenylalanine 4-nitrophenyl ester (S 2 ) enantiomers promoted by CuL 1 , which exhibited an enantiomer selectivity of 15.7. We observed preferential hydrolysis of L -S 2 by CuL 1 , even in racemic S 2 , through chiral high-performance liquid chromatography (HPLC). We demonstrated that the enantioselective hydrolysis was related to the cooperative roles of the intramolecular flanking chiral CD cavities with the coordinated copper ion, according to the results of electrospray ionization mass spectrometry (ESI-MS), inhibition experiments, rotating-frame nuclear Overhauser effect spectroscopy (ROESY), and theoretical calculations. Although the catalytic parameters lag behind the level of enzymatic transformation, this study confirms the cooperative effect of the first and second coordination spheres of artificial catalysts in enantioselectivity and provides hints that may guide future explorations of enzyme mimics.
研究领域:
化学
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生物催化
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材料科学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF CHEMICAL THERMODYNAMICS
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2013
·
IF 2.297
Jun Jing,Zhiyong Li,Yuanchao Pei,Huiyong Wang,Jianji Wang
In this work, a series of novel room temperature ionic liquids (ILs) have been synthesized with cheap, naturally α-amino acid ester as cations and bis(trifluoromethylsulfonyl)imide as anion. The glass transition temperature and thermal decomposition temperature of these ILs, partition coefficients of some coumarins and purine alkaloids between water and the amino acid ester-based ILs at T = 298.15 K, and Gibbs energy, enthalpy and entropy changes for the transfer of caffeine and 6,7-dihydroxycoumarin from water to [LeuC 2 ][Tf 2 N] have been determined. It is shown that these ILs are highly effective materials for the extraction of drug compounds like coumarin, 4-hydroxycoumarin, 7-hydroxycoumarin, 3-aminocoumarin, coumarin-3-carboxylic acid, 6,7-dihydroxycoumarin, 6,7-dihydroxy-4-methylcoumarin, caffeine, theobromine, theophylline, inosine, and 2,6-diaminopurine. The partition process is driven by enthalpy term, and partition coefficients of the drug molecules increase with the increase of hydrophobicity of both the drug molecules and the ILs. Furthermore, the possible partition mechanism has been investigated from 13 C NMR measurements.
研究领域:
药学
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化学
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产品关联
DOI
高影响因子
FITOTERAPIA
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2024
·
IF 2.5
Hongliu Xie,Fang Lin,Fei Shi,Elaine Johnstone,Yaqi Wang,Yang An,Jun Su,Jiayin Liu,Qinghai Dong,Jihua Liu
As one of the metabolites of ginseng, 20( S )-protopanaxadiol (PPD) is a compound with dammarane-type tetracyclic triterpene, which performs a wide range of anticancer activities. In this study, PPD was used as a lead. A series of compounds were synthesized respectively with 11 amino acids through esterification and were evaluated for their cytotoxicity against several cancer cell lines. One of the synthetic products (PL) exhibited potent inhibitory effect on Huh-7 cells relative to that of PPD in vitro. Subsequently, the Annexin V-FITC /PI staining assay was used to verify that PL induced apoptosis of Huh-7 cells in a dose-dependent manner. A UPLC-Q/TOF-MS analysis method was established and validated for assessing pharmacokinetic properties after the administration of PPD and PL in rats. The results showed that compared with PPD, T 1/2 of PL in rats was prolonged, and the peak time was delayed, resulting in broader tissue distribution of the compound in the body. In addition, the targets of PL against several cancers were predicted and analyzed via network pharmacology. Molecular docking simulations demonstrated that PL interacted with the active sites of the above targets. In conclusion, this study provided a theoretical basis for the development and clinical application of anti-tumor activity of PPD.
研究领域:
药理学
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肿瘤学
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中药化学
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产品关联
DOI
PubMed
高影响因子
TALANTA
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2013
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IF 3.498
Jinjing Zhang,Yingxiang Du,Qi Zhang,Yuntao Lei
Recently, chiral ionic liquids (ILs) have drawn increasing attention in chiral separation field; however, few papers reported the application of chiral ILs for chiral separation by capillary electrophoresis (CE), and among the papers, chiral ILs were mainly applied as additives to β-cyclodextrin derivatives systems to establish synergistic systems. The synergistic system based on antibiotics with chiral ILs as additives has never been reported before. In this paper, two chiral ionic liquids (ILs) based on amino acid ester , l -alanine and l -valine tert butyl ester bis (trifluoromethane) sulfonamide, were first applied to evaluate the synergistic effect with antibiotic selector for CE chiral separation. The vancomycin-based synergistic system with chiral ILs as additives was successfully established and investigated for the enantioseparation of naproxen , carprofen , ibuprofen , ketoprofen and pranoprofen . Compared to vancomycin-alone cases, significant improvement of separation for all the analytes was observed. Several parameters, such as type and proportion of organic modifier, composition and pH of buffer, concentration of chiral ILs and vancomycin were systematically investigated, and then evaluated by means of Statistical Product and Service Solutions (SPSS) to research the influences on the synergistic effect. Finally, the established method was successfully applied to test the chiral impurity of naproxen sample.
研究领域:
分析化学
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药物分析
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分离科学
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DOI
PubMed
高影响因子
TALANTA
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2015
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IF 3.545
Xiaohua Zhou,Xiaole Li,Aijuan Cao,Qiao Lijun,Ajuan Yu,Shusheng Zhang,Yangjie Wu
A new stationary phase for high-performance liquid chromatography was prepared by covalently bonding N-ferrocenyl(benzoyl)amino-acid esters (L 1 ) onto silica gel using 3-aminopropyltriethoxysilane as coupling reagent. The structure of new material was characterized by infrared spectroscopy , elemental analysis and thermogravimetric analysis . The chromatographic behavior of the phase was illustrated in reversed-phase (RP) and normal-phase (NP) modes using polycyclic aromatic hydrocarbons (PAHs), aromatics positional isomers, amines, 5-nitroimidazoles, organophosphorus pesticides and phenols as probes. Multiple mechanisms including hydrophobic, hydrogen bonding , π–π, dipole–dipole, charge-transfer and acid–base equilibrium interactions are involved. Thus, multi-interaction mechanisms and mixed-mode separation of the new phase can very likely guarantee its excellent chromatographic performance for the analysis of complex samples. The L 1 AminoSil column was successfully employed for the analysis of organophosphorus pesticides in vegetable.
研究领域:
分析化学
·
色谱技术
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DOI
高影响因子
JOURNAL OF CHEMICAL RESEARCH
·
2018
·
IF 0.668
Song Bai,Shan Liu,Yunying Zhu,Jiali Lu,Lina Ai,Jing Xue,Qin Wu
An efficient asymmetric synthesis of chiral β-amino acid ester derivatives containing a 4-(pyridin-3-yl)pyrimidin-2-yl amine moiety was developed. This catalytic asymmetric Mannich reaction gave target products in high yields (95%) and excellent enantioselectivities (>99% ee) using a cinchona-based squaramide catalyst under solvent-free, one-pot conditions. Antiviral bioassays indicated that some of the chiral products exhibited higher antiviral activities against tobacco mosaic virus than the commercial compound ribavirin.
研究领域:
有机化学
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药物化学
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病毒学
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DOI
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
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2019
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IF 4.561
Pan Zhang,Lemeng Wang,Chunjie Lu,Mengying Li,Shujun Yu,Dong Fu
The surface tensions of 2‑diethylaminoethanol (DEAE)‑ N ‑(2‑aminoethyl)ethanolamine (AEEA), DEAE‑ N ‑methyl‑1,3‑propane‑diamine (MAPA) and DEAE‑1,4‑butanediamine (BDA) aqueous solutions have been measured by using the BZY-1 surface tension meter. The mass fractions of DEAE and AEEA/MAPA/BDA respectively ranged from 0.300 to 0.500 and 0.050 to 0.150. The temperature ranged from 303.2 K to 323.2 K. A thermodynamic equation was proposed to model the surface tension and the calculated results agreed well with the experiments. The effects of temperature and mass fraction of amines on the surface tension were demonstrated on the basis of experiments and calculations. The surface thermodynamics including surface enthalpy and surface entropy of blended amine aqueous solutions were also determined, and their temperature and mass fraction dependences were analyzed.
研究领域:
物理化学
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溶液化学
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热力学
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表面科学
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化工材料
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DOI
高影响因子
Food Bioscience
·
2024
·
IF 4.8
Jiaxuan Wang,Cuiping Pang,Zhonglin Tu,Jianghua Li,Guocheng Du,Guoqiang Zhang
L-Alanyl- l -Glutamine (Ala-Gln) is a kind of functional dipeptide , which is widely used in food and health care. Ala-Gln can be synthesized from l -glutamine and l -alanine methyl ester hydrochloride by α-Amino acid ester acyltransferase (AET). Still, the low catalytic efficiency and conversion rate of AET are key limiting factors in Ala-Gln production. In this study, the mutant library of AET were built based on structural model and semi-rational design. To facilitate the screening of AET mutants, the double enzymes coupled screening method was constructed and optimized. The amino acid residues I115, D203, F211, D300, A298, and R334 were selected as candidate mutation sites by alanine scanning and virtual saturation mutation and the catalytic activity of the optimal mutation A298C increased by 23.7%. Molecular dynamics simulation and molecular docking analysis suggested that the increased flexibility of the catalytic pocket in AET (A298C) and the formation of additional hydrogen bonds with substrate contributed to the improvement of enzyme activity .
研究领域:
生物化学
·
酶工程
·
食品科学
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产品关联
DOI
高影响因子
Microbial Cell Factories
·
2019
·Vol. 18
·期 1
·1-12
·
IF 4.402
Li Yi-Min,Gao Jiao-Qi,Pei Xu-Ze,Du Cong,Fan Chao,Yuan Wen-Jie,Bai Feng-Wu
Background l-Alanyl-l-glutamine (Ala-Gln) represents the great application potential in clinic due to the unique physicochemical properties. A new approach was developed to synthesize Ala-Gln by recombinant Escherichia coli OPA, which could overcome the disadvantages of traditional chemical synthesis. Although satisfactory results had been obtained with recombinant E. coli OPA, endotoxin and the use of multiple antibiotics along with toxic inducer brought the potential biosafety hazard for the clinical application of Ala-Gln.Results In this study, the safer host Pichia pastoris was applied as an alternative to E. coli. A recombinant P. pastoris (named GPA) with the original gene of α-amino acid ester acyltransferase (SsAet) from Sphingobacterium siyangensis SY1, was constructed to produce Ala-Gln. To improve the expression efficiency of SsAet in P. pastoris, codon optimization was conducted to obtain the strain GPAp. Here, we report that Ala-Gln production by GPAp was approximately 2.5-fold more than that of GPA. The optimal induction conditions (cultivated for 3 days at 26 °C with a daily 1.5% of methanol supplement), the optimum reaction conditions (28 °C and pH 8.5), and the suitable substrate conditions (AlaOMe/Gln = 1.5/1) were also achieved for GPAp. Although most of the metal ions had no effects, the catalytic activity of GPAp showed a slight decrease in the presence of Fe3+ and an obvious increase when cysteine or PMSF were added. Under the optimum conditions, the Ala-Gln generation by GPAp realized the maximum molar yield of 63.5% and the catalytic activity of GPAp by agar embedding maintained extremely stable after 10 cycles.Conclusion sCharacterized by economy, efficiency and practicability, production of Ala-Gln by recycling immobilized GPAp (whole-cell biocatalyst) is represents a green and promising way in industrial.
研究领域:
生物技术
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酶学
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药物化学
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合成生物学
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DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）