BIOORGANIC CHEMISTRY
·
2020
·
IF 4.831
Huan Li,Shuang Fu,Yudan Wang,Xuan Yuan,Lijia Liu,Hongxing Dong,Qiang Wang,Zhijia Zhang
Thirteen cationic peptidomimetics derived from amino acids bearing an alkyl or ethynylphenyl moiety that mimic the structure of cationic antibacterial peptides were designed and synthesized using a simple coupling reaction of an amino acid with a substituted amine. Antibacterial activities of the resulting peptidomimetics against drug-sensitive bacteria, such as Gram-positive Staphylococcus aureus ( S. aureus ) and Bacillus subtilis , Gram-negative Escherichia coli ( E. coli ) and Salmonella enterica , and a drug-resistant bacterium, methicillin-resistant S. aureus (MRSA), were systematically evaluated. Most peptidomimetics show significant broad-spectrum antibacterial activity. A-L-Iso-C 12 (isoleucine derivative bearing a dodecyl moiety) show MICs of 2.5 μg/mL against S. aureus and 4 μg/mL against MRSA and A-L-Val-C 12 (valine derivative bearing a dodecyl moiety) show MICs of 1.67 μg/mL against E. coli and 8.3 μg/mL against MRSA. A-L-Val-C 12 showed low cytotoxicity toward L929 cells in comparison with SGC 7901 cells, indicating tumor-directed killing by peptidomimetics while avoiding toxicity to normal cells. The influences of type of amino acid and substituent, length of substituent, and stereochemistry of amino acids on antibacterial activity and cytotoxicity of peptidomimetics were systematically investigated. The results indicate that this series of cationic peptidomimetics derived from amino acids display antitumor activity and may be useful for treatment of bacterial infections.
研究领域:
微生物学
·
药理学
·
分子生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
CHEMICAL & PHARMACEUTICAL BULLETIN
·
2016
·Vol. 64
·期 10
·1466-1473
·
IF 1.228
En-bo Cai,Li-min Yang,Cai-xia Jia,Wei-yuan Zhang,Yan Zhao,Wei Li,Xing-zhuo Song,Man-ling Zheng
The use of arctigenin (ARG), a traditional medicine with many pharmacological activities, has been restricted due to its poor solubility in water. Five amino acid derivatives of ARG have been synthesized using glycine, o-alanine, valine, leucine, and isoleucine, which have t-butyloxy carbonyl (BOC) as a protective group. In this study, we examined the effects of removing these protective groups. The results showed that the amino acid derivatives have better solubility and nitrite-clearing ability than ARG. Among the compounds tested, the amino acid derivatives without protective group were the best. Based on these results, ARG and its two amino acid derivatives without protective group (ARG8, ARG10) were selected to evaluate their anti-tumor activity in vivo at a dosage of 40 mg/kg. The results indicated that ARG8 and ARG10 both exhibit more anti-tumor activity than ARG in H22 tumor-bearing mice. The tumor inhibition rates of ARG8 and ARG10 were 69.27 and 43.58%, which was much higher than ARG. Furthermore, the mice treated with these compounds exhibited less damage to the liver, kidney and immune organs compared with the positive group. Furthermore, ARG8 and ARG10 improved the serum cytokine levels significantly compared to ARG. In brief, this study provides a method to improve the water solubility of drugs, and we also provide a reference basis for new drug development.
研究领域:
药理学
·
药物化学
·
肿瘤学
✓ 已验证
DOI
PubMed
高影响因子
JOURNAL OF POWER SOURCES
·
2024
·
IF 8.1
Suqi Huo,Wenyue Zhang,Yujie Qiang,Ye Zhang,Subramanian Sundarrajan,Lei Guo,Tianhu Liu,Seeram Ramakrishna
Aluminum-air batteries, known for their high energy density and environmental friendliness, often face significant challenges due to the corrosion of aluminum anodes, which limits their performance and lifespan. The corrosion inhibition effect of eco-friendly N-α-Fmoc-N-epsilon-Boc-D-lysine (FDLH) in alkaline aluminum-air battery on Al-5052 anodes is investigated by H 2 evolution experiments, electrochemical tests, microscopic characterization, spectroscopic examination, and simulated calculations. It demonstrates that the carboxyl oxygen in the molecular structure of FDLH has good coordination with the Al. FDLH can form an adsorption film on the surface of Al-5052 anode, achieving the purpose of protecting the Al-5052 anode from corrosion. Furthermore, the adsorption behavior of the FDLH plays a crucial role in achieving uniform anode discharge potential and enhancing electrochemical performance. At an optimal concentration of 7 mM FDLH, the inhibition efficiency reaches 57.1 %, while the anode utilization rate increases to 85.0 %. These findings highlight the potential of FDLH as an effective corrosion inhibitor, contributing to the improvement of both the durability and efficiency of aluminum-air battery systems.
研究领域:
材料科学
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电化学
·
环境科学
✓ 已验证
DOI
高影响因子
Artificial Cells Nanomedicine and Biotechnology
·
2020
·
IF 3.343
Beibei Hu,Haipeng Yan,Yanping Sun,Xi Chen,Yujuan Sun,Sanming Li,Yongshuai Jing,Heran Li
Organogels are excellent drug carrier for controlled release. Organogels based on amino acid derivatives has been widely used in the area of drug delivery. In this study, a series of the organogel system based on amino acid derivatives gelators was designed and prepared to investigate the structure-property correlation in organogels. To investigate the factors that influence the property of drug release, we varied the formulation in the organogels: gelator structure, gelator concentration, volume of antigelation solvent, and drug loading. Through the Box–Behnken tests, the optimum organogel formulation in vitro was obtained. The self-healing properties of the organogel have been utilised for injection of a model lipophilic risperidone in situ, and sustained release of the drug has been studied over about one week in vivo. In conclusion, the gelation ability of gelators could be adjusted by the gelator structure. Gel property is related with the whole composition of the formulation. As drug carrier, the drug release property of organogels is affected by multiple factors. Our investigation of the gel release property will play a theoretical guiding role in the application in the in situ drug delivery system.
研究领域:
药剂学
·
材料科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Science China-Materials
·
2024
·Vol. 67
·期 5
·1521-1532
·
IF 6.8
Li Meng,Zhang Mengyuan,Liu Zheng,Xie Ruilin,Yang Yuxuan,Shen Kaixiang,Yang Aimin,Cheng Yilong
The design and fabrication of injectable barriers with promising antifouling capability to prevent the formation of adhesions after surgery remains challenging. Herein, we introduce amino acid derivative with hydroxyl group ( N -acryloyl serine (ASer)) into the preparation of hydrogels to develop a novel hydrogen bond-crosslinked hydrogel (PASer) by free radical polymerization. It is found that one substituted methyl group can cause considerable disruption to the hydrogen bonding interaction and result in increased initial gelling concentration and significant decrease in the mechanical properties of poly( N -acryloyl threonine) (PAThr) hydrogel compared with PASer hydrogel. Moreover, it is worth noting that the hydrophilic hydroxyl groups enable PASer hydrogel to efficiently resist protein adsorption and cell adhesion. The PASer hydrogel possesses excellent mechanical performance, injectability, self-fusion, good biocompatibility and appropriate in vivo residence time, which are consistent with the requirements of postoperative anti-adhesion materials in clinical practice. In vivo studies reveal that the advanced hydrogel shows satisfactory preventive effect on postoperative peritoneal adhesions in the established mice abdominal wall defect model.
研究领域:
生物材料学
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医学工程
·
组织工程
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF CHROMATOGRAPHY A
·
2014
·
IF 4.258
Qiqin Wang,Jun Feng,Hai Han,Peijie Zhu,Huihui Wu,Maria Luisa Marina,Jacques Crommen,Zhengjin Jiang
In order to obtain satisfactory column permeability, efficiency and selectivity for micro-HPLC, a capillary monolithic column containing O -9-[2-(methacryloyloxy)-ethylcarbamoyl]-10,11-dihydroquinidine (MQD) as chiral selector was re-optimized. The monolithic column was used to successfully enantioresolve a wide range of N-derivatized amino acids including alanine, leucine, methionine, threonine, phenylalanine, valine, serine, isoleucine, tryptophan, and cysteine. The influence of mobile phase parameters, such as the organic solvent type and concentration, the apparent pH, and buffer concentration, on retention and enantioseparation of N-derivatized amino acids has been investigated. 3,5-dinitrobenzoyl-amino acids and 3,5-dichlorobenzoyl-amino acids were resolved into enantiomers with exceptionally high selectivity and resolution. The chemoselectivity of the monolithic column for a multicomponent mixture of N-derivatized amino acids was also investigated. A mixture of three pairs of 3,5-dichlorobenzoyl-amino acids could be fully resolved in 22.5 min.
研究领域:
分析化学
·
色谱技术
✓ 已验证
DOI
高影响因子
INTERNATIONAL JOURNAL OF POLYMER ANALYSIS AND CHARACTERIZATION
·
2017
·
IF 0
Shouhui Yi,Bo Yang,Rongqiang Liao
A series of novel pendant polymers, composed of a poly(ε-lysine) (ε-PL) (w: 4,000 g mol−1) main chain and three kinds of amino acid β-cyclodextrin (CD) derivatives, were prepared by 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride and N-hydroxysuccinimide-assisted synthesis and characterized by nuclear magnetic resonance, Fourier transform infrared spectroscopy, thermal gravimetric analysis, X-ray power diffraction, and scanning electron microscopy. Cytotoxicity and moisture absorption of the pendant polymers were also tested. Compared with ε-PL, all the pendant polymers exhibited lower moisture absorption and cytotoxicity. The synthesis method of the pendant polymers is simple, feasible, and has good practicability. We suggest these polymers have potential applications in many fields, especially in gene delivery vector and drug delivery systems.
研究领域:
高分子化学
·
生物材料
·
药物递送系统
✓ 已验证
产品关联
DOI
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
·
2024
·
IF 2.9
Lei Guo,Lei Zhu,Yue Huang,Yan Tan,Alessandra Gilda Ritacca,Xingwen Zheng,Senlin Leng,Baoguo Wang
Alkaline Al-air batteries (AABs) are gaining increasing attention for large-scale energy storage systems due to their attractive intrinsic safety and cost-effectiveness. Nonetheless, future development of AABs is substantially hampered by water-induced self-corrosion processes on the Al anode. In this work, we introduce an amino acid derivative, namely Nα-Boc-N1-formyl-L-tryptophan (NBLT), into 4 M NaOH electrolyte to construct a unique layer that can effectively regulate the surface microstructure of Al anode. The findings of the experiments show that NBLT can be used as a reliable corrosion inhibitor. The effectiveness of the inhibitor increases with NBLT concentration, reaching a maximum of 73.9% at 1.5 mM. In comparison to the pristine condition, there is a significant increase in anode utilization from 31.8% to 82.9%, capacity density from 947.9 to 2469.1 mAh g−1, and energy density from 1261.6 to 3384.6 Wh kg−1. Theoretical calculations indicate that the carboxyl moieties present in the NBLT molecule establish coordination bonds with the Al atoms, thereby exerting a dominant role on the formation of the self-assembled barrier. The present investigation paves an effective strategy to inhibit reactions between anodes and electrolytes for advanced AABs.
研究领域:
材料科学
·
电化学
✓ 已验证
DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF PHARMACEUTICS
·
2018
·
IF 3.862
Beibei Hu,Wei Sun,Haiting Li,Helin Sui,Sanming Li
Thermogels, used as multi-functional drug-loading materials, have properties that mainly rely on their gelator structure. Although a large variety of organogel systems are used as drug delivery carriers, relatively few have been investigated in terms of their structure-property correlations based on amino acid derivative gelators. Here, a series of amino acid based gelators were synthesized to explore the role of the gelator structure on functional properties, with the aim of establishing a connection between the molecular parameters and gel properties. By varying the three substitutions of the gelator backbone, it was found that a comprehensive interaction, consisting of hydrophobic forces, H-bonding interactions, conformational flexibility and steric repulsion, play a crucial role in determining the gelation properties. Hansen solubility parameters were employed to explore the solvent effect on the network forming and gel properties. From an analysis of the morphologies obtained from polarized optical microscope (POM), atomic force microscopic images (AFM) and scanning electron microscopy (SEM), the gelator structure was found to have an impact on the self-assembly. According to the X-ray diffraction (XRD), the possible conformations adopted by the gelators were revealed through molecular modelling. The ability to form intermolecular H-bonding is vital in molecular packing and, thus, gelation. A structure-property relationship was developed and proposed to provide a theoretical basis for controllable drug delivery implants.
研究领域:
材料科学
·
药学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
CHINESE JOURNAL OF POLYMER SCIENCE
·
2024
·Vol. 42
·期 10
·1578-1588
·
IF 4.1
Li Meng,Zhang Meng-Yuan,Lei Wu-Xuan,Lv Zhu-Ting,Shang Qing-Hua,Zhao Zheng,Li Jiang-Tao,Cheng Yi-Long
The development of physically crosslinked hydrogels with excellent mechanical and sensing properties is of importance for expanding the practical applications of intelligent soft hydrogel materials. Herein, after copolymerization of hydroxyl-containing amino acid derivative N-acryloyl serine (ASer) with acrylamide (AM), we introduce Zr 4+ through an immersion strategy to construct metal ion-toughened non-covalent crosslinked hydrogels (with tensile strength of up to 5.73 MPa). It is found that the synergistic coordination of hydroxyl and carboxyl groups with Zr 4+ substantially increases the crosslinking density of the hydrogels, thereby imparting markedly superior mechanical properties compared to hydroxyl-free Zr 4+ -crosslinked hydrogels, such as N-acryloyl alanine (AAla) copolymerized with AM hydrogels (with tensile strength of 2.98 MPa). Through the adjustment of the composition of the copolymer and the density of coordination bonds, the mechanical properties of the hydrogels can be modulated over a wide range. Additionally, due to the introduction of metal ions and the dynamic nature of coordination bonds, the hydrogels also exhibit excellent sensing performance and good self-recovery properties, paving the way for the development of flexible electronic substrates with outstanding comprehensive performances.
研究领域:
材料科学
·
高分子化学
·
智能材料
✓ 已验证
DOI
高影响因子
JOURNAL OF CHROMATOGRAPHY A
·
2013
·
IF 4.612
Jinjing Zhang,Yingxiang Du,Qi Zhang,Jiaquan Chen,Guangfu Xu,Tao Yu,Xiaoyi Hua
Recently, chiral ionic liquids (ILs) have drawn more and more attention in chiral separation by capillary electrophoresis (CE). In this paper, two chiral ILs based on amino acid derivatives, l -alanine and l -valine tert butyl ester bis (trifluoromethane) sulfonimide, were applied for the first time in CE to evaluate their potential synergistic effects with classical chiral selectors (β-cyclodextrin derivatives) for enantiomeric separation. As observed, improved separation of tested drug enantiomers was obtained with the presence of chiral ILs compared to the conventional β-cyclodextrin derivatives separation system. Parameters such as type and proportion of organic modifier, type and concentration of chiral ILs, concentration of chiral selector, buffer pH and applied voltage were systematically investigated with Me-β-CD/chiral ILs as model system to optimize the novel synergistic system, and the best results were obtained when 15 mM chiral ILs were introduced into the 30 mM sodium citrate/citric acid (20% organic modifier included) buffer solution containing 20 mM Me-β-CD at pH 5.0 with a 20 kV applied voltage for naproxen, pranoprofen and warfarin.
研究领域:
分析化学
·
药物化学
✓ 已验证
DOI
PubMed
高影响因子
JOURNAL OF SEPARATION SCIENCE
·
2014
·Vol. 38
·期 2
·332-338
·
IF 2.594
Bingxiang Wang,Weibo Chai,Guosheng Ding
In this study, diamino moiety functionalized silica nanoparticles with the size of 118 ± 12 nm were successfully synthesized and directly introduced into a chiral capillary electrophoresis system to improve the enantioseparation of 9-fluorenyl methoxycarbonyl derivatized amino acids using norvancomycin as chiral selector. Under acidic background electrolyte conditions, functional silica nanoparticles can be readily adsorbed onto the inner surface of bare silica capillary column through electrostatic interaction to form a dynamic coating, resulting in a reversed anodic electro-osmotic flow (i.e. from cathode to anode). As expected, chiral amino acid derivatives (usually negatively charged) can be rapidly separated under co-electro-osmotic flow conditions in the current separation system. Furthermore, the column performance and detection sensitivity for the enantioseparation were also obviously improved because the adsorption of chiral selector of norvancomycin to the capillary wall was greatly suppressed. Some important factors influencing the separation, such as the coating thickness, background electrolyte concentration, functional silica nanoparticles concentration, and the organic modifier were also investigated and the optimized separation conditions were obtained.
研究领域:
分析化学
·
纳米技术
·
药物化学
✓ 已验证
DOI
高影响因子
危险品化学品经营许可证（带存储）