Materials Today Chemistry
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2018
·
IF 0
A. Kousar,J. Liu,N. Mehwish,F. Wang,A.Y. Dang-i,C. Feng
To achieve desired physicochemical and biochemical activities of optically active molecules at targetted sites in biological systems, tuning of chiral sense by varying internal conditions (e.g., pH) is of utmost importance. However, it has been a challenge to gain the balance of non-covalent interactions required for chiral transformations merely by deviations in biochemical environment. Herein, pH-controlled chirality of supramolecular nanostructures obtained from coassembly of phenylalanine-derived gelator and achiral cationic polyacrylamide has successfully been achieved. Specifically, any changes in the pH remarkably influence the chirality of these nanostructures. For instance, coassembled hydrogels possessing l -enantiomer provide right-handed nanostructures at pH < 7; whereas at pH ≥ 7, handedness of nanostructures switches to the left-handed nanostructures. Moreover, viscoelastic properties and twist pitch were also regulated under the influence of pH change. This study may provide a methodology to control chirality by simply varying biochemical conditions, which points toward its potential to be used in biological systems as a key to gain preferential chiral sense in different sites of living systems.
研究领域:
材料科学
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生物学
·
化学
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产品关联
DOI
ANALYTICAL AND BIOANALYTICAL CHEMISTRY
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2018
·Vol. 410
·期 23
·5941-5950
·
IF 3.307
Peng Huanjun,Wang Xiang,Peng Jingdong,He Yan,Chen Yu,Chen Fang,Li Shiyu
4-Hydroxy- d -phenylglycine was modified with methacrylic anhydride and then immobilized on silica through thiol-initiated surface polymerization; the prepared material was applied as stationary phase for HPLC. The obtained stationary phase was characterized by elemental analysis, infrared spectroscopy, and thermogravimetric analysis. The chromatographic performance of the packed column was evaluated in reversed-phase liquid chromatograph (RPLC) and hydrophilic interaction liquid chromatograph (HILIC) mode; this column has shown excellent selectivity to both the hydrophobic and hydrophilic solutes. The selectivity towards polycyclic aromatic hydrocarbons relative to that towards alkylbenzenes exhibited by the prepared column was higher than the corresponding selectivity exhibited by commercial C18 column, which could be explained by electronic π-π interaction between phenylglycine and electron-rich aromatic rings. On the other hand, the prepared column has also shown better selectivity for polar compounds, which was based on the multiple interaction and retention mechanisms. It was also used to separate sulfonamides and organic acid compared with a commercial C18 and HILIC column; the results show its great chromatographic performance with distinctive selectivity. All the results indicated the prepared column had potential application in a wide range.
研究领域:
分析化学
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材料科学
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色谱技术
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DOI
高影响因子
MACROMOLECULAR BIOSCIENCE
·
2018
·Vol. 18
·期 6
·1800054
·
IF 3.392
Rong Wang,Fanjun Zhang,Weiwei Lin,Wenkai Liu,Jiehua Li,Feng Luo,Yaning Wang,Hong Tan
Biodegradable shape memory polymers are promising biomaterials for minimally invasive surgical procedures. Herein, a series of linear biodegradable shape memory poly(ε-caprolactone) (PCL)-based polyurethane ureas (PUUs) containing a novel phenylalanine-derived chain extender is synthesized. The phenylalanine-derived chain extender, phenylalanine-hexamethylenediamine-phenylalanine (PHP), contains two chymotrypsin cleaving sites to enhance the enzymatic degradation of PUUs. The degradation rate, the crystallinity, and mechanical properties of PUUs are tailored by the content of PHP. Meanwhile, semicrystalline PCL is not only hydrolytically degradable but also vital for shape memory. Good shape memory ability under body temperature is achieved for PUUs due to the strong interactions in hard segments for permanent crosslinking and the crystallization-melt transition of PCL to switch temporary shape. The PUUs would have a great potential in application as implanting stent.
研究领域:
生物医学工程
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材料科学
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DOI
PubMed
高影响因子
Science Advances
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2023
·Vol. 9
·期 22
·
IF 13.6
Jing Yu,Ruilin Xie,Mengyuan Zhang,Kaixiang Shen,Yuxuan Yang,Xiaodan Zhao,Xin Zhang,Yanfeng Zhang,Yilong Cheng
Development of underwater adhesives with instant and robust adhesion to diverse substrates remains challenging. A strategy taking the structural advantage of phenylalanine derivative, N-acryloyl phenylalanine (APA), is proposed to facilely prepare a series of underwater polymeric glue-type adhesives (UPGAs) through one-pot radical polymerization with commonly used hydrophilic vinyl monomers. The adjacent phenyl and carboxyl groups in APA realize the synergy between interfacial interactions and cohesion strength, by which the UPGAs could achieve instant (~5 seconds) and robust wet tissue adhesion strength (173 kilopascal). The polymers with varied hydrophobicity and substitutional groups as well as carboxyl and phenyl groups in separated components are designed to investigate the underwater adhesion mechanism. The universality of APA for the construction of UPGAs is also verified by the copolymerization with different hydrophilic monomers, and the applications of the UPGAs have been validated in diverse hemorrhage models and distinct substrates. Our work may give a promising solution to design potent underwater adhesives.
研究领域:
材料科学
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生物医学工程
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高分子化学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF SEPARATION SCIENCE
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2015
·Vol. 38
·期 12
·2085-2092
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IF 2.737
Shengqiang Tong,Mangmang Shen,Hu Zhang,Dongping Cheng,Jizhong Yan
The chromatographic retention mechanism describing relationship between retention factor and concentration of Cu 2+ ( l -phenylalanine) 2 using chiral ligand mobile phase was investigated and eight mandelic acid derivatives were enantioseparated by chiral ligand exchange chromatography. The relationship between retention factor and concentration of the Cu 2+ ( l -phenylalanine) 2 complex was proven to be in conformity with chromatographic retention mechanism in which chiral discrimination occurred both in mobile and stationary phase. Different copper(II) salts, chiral ligands, organic modifier, pH of aqueous phase, and conventional temperature on retention behavior were optimized. Eight racemates were successfully enantioseparated on a common reversed-phase column with an optimized mobile phase composed of 6 mmol/L of l -phenylalanine or N , N -dimethyl- l -phenylalanine and 3 mmol/Lof copper(II) acetate or copper(II) sulfate aqueous solution and methanol.
研究领域:
分析化学
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药物化学
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DOI
高影响因子
Gels
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2025
·Vol. 11
·期 2
·112
·
IF 5.3
Beibei Wu,Xiaoqiu Dou,Sravan Baddi,Fengli Gao,Changli Zhao,Chuanliang Feng
Osteoporosis, a chronic bone disorder, poses a global threat to the health of millions of individuals. The disruption of bone homeostasis is the fundamental cause of osteoporosis. Currently, clinical drugs are employed to promote bone formation via enhancing osteogenesis and/or reduce bone loss via inhibiting osteoclastogenesis. However, it is difficult for the current drugs to simultaneously address the osteoblastogenesis and osteoclastogenesis issues associated with osteoporosis. Hence, L/D-phenylalanine derivatives (L/DPF), combined with Mg2+ions, are employed to assemble into chiral supramolecular hydrogels which facilitate osteocyte activity and inhibit osteoclast function. LPF_Mg hydrogels and DPF_Mg hydrogels demonstrate the opposite supramolecular chirality. Specifically, LPF_Mg hydrogels and DPF_Mg hydrogels are composed of left-handed (M-type) helical nanofibers and right-handed (P-type) helical nanofibers, respectively. The hydrogen bonding and π–π stacking interactions are crucial in the process of hydrogel formation. The chiral left-handed nanofibrous DPF_Mg hydrogels significantly promote osteogenic differentiation of MC3T3 cells and inhibit osteoclast differentiation of RAW267.4 cells, thereby demonstrating substantial potential for applications in improving skeletal health. These findings provide a promising novel perspective on the application of chiral functional materials for osteoporosis therapy.
研究领域:
生物材料学
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骨生物学
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医学
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产品关联
DOI
PubMed
高影响因子
MACROMOLECULAR CHEMISTRY AND PHYSICS
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2015
·Vol. 216
·期 19
·1945-1951
·
IF 2.616
Wei Ji,Guo Feng Liu,Ming Xin Xu,Chuan Liang Feng
A novel and simple strategy for preparing a redox-responsive supramolecular hydrogel coassembled from phenylalanine derivative gelator and 4,4′-dipyridine disulfide is reported in this study. The driving force for the coassembly process is intermolecular hydrogen bonds, as confirmed by various characterization methods, such as 1 H NMR, Fourier transform infrared (FTIR) spectroscopy, and circular dichroism spectroscopy. The disulfide-containing nanofibrous hydrogel is able to control over the release of encapsulated dyes in response to the reductive condition mimicking the intracellular environment like tumor tissues and should be a promising system for controllable drug release in the fields of nanomedicine and cancer therapy.
研究领域:
纳米医学
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癌症治疗
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材料科学
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生物化学
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产品关联
DOI
高影响因子
Chemical Science
·
2017
·Vol. 8
·期 3
·1769-1775
·
IF 8.668
Guofeng Liu,Jinying Liu,Chuanliang Feng,Yanli Zhao
The construction of chiral supramolecular systems with desirable handedness is of great importance in materials science, chemistry, and biology since chiral nanostructures exhibit fascinating photophysical properties and unique biological effects. Herein, we report that achiral bipyridines can co-assemble with L-phenylalanine derivatives into unexpected right-handed helical nanostructures rather than a left-handed helix via intermolecular hydrogen bonding interactions formed between the pyridyl and carboxylic groups. This study opens up a route to develop chiral nanostructures with desirable handedness via the co-assembly of simple molecular building blocks and provides a straightforward insight into the chirality control of nanostructures in supramolecular systems.
研究领域:
材料科学
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化学
·
生物学
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产品关联
DOI
PubMed
高影响因子
ORGANIC PROCESS RESEARCH & DEVELOPMENT
·
2024
·
IF 3.1
Chuanjun Wu,Heng Guo,Jiawei Tang,Lintao Xia,Jianfen Shao,Yongfu He,Fei Chen,Peng Peng,Yuewen Han,Chuanmeng Zhao,Fuli Zhang,Shaoxin Chen
In the present study, a practical chemoenzymatic method was developed for the synthesis of chiral phenylalanine derivative 1, which is the key intermediate of Lifitegrast. In this established process, a simple and effective Zn/HCl reduction system was employed to obtain N-acetyl-3-bromo-phenylalanine 6, which served as the substrate for the subsequent enzymatic resolution process. Then, the key chiral intermediate, 3-bromo-l-phenylalanine 7, could be obtained using acylase (ACY) AmACY. Upon process optimization, the chemical reaction was executed at a 300 g scale, with a notable substrate concentration reaching up to 100 g/L. The process achieved a yield of 40%, compared to a maximum theoretical yield of 50%, and exhibited an enantiomeric excess (ee) value reaching up to 99.9%. A simple and effective Zn/HCl reduction system was employed to obtain N-acetyl-3-bromo-phenylalanine 6, which served as the substrate for the subsequent enzymatic resolution process. This synthetic pathway was effectively executed, yielding 1·HCl with a purity of 99.7% and an ee value of 99.9%, culminating in an overall yield of 23.4%. Additionally, the undesired (D)-6 enantiomer was recycled to form (rac)-6, employing an acetanhydride/acetic acid (Ac2O/AcOH) system. This recycling process achieved a yield of 47.5%, relative to a maximum theoretical yield of 50%, and a purity level of 99.8%.
研究领域:
药物化学
·
生物催化
·
有机合成
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DOI
高影响因子
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES
·
2016
·Vol. 32
·期 5
·872-876
·
IF 1.086
Yu Ye,Wang Yuxiang,Feng Chuanliang
A roadblock for supramolecular hydrogels is their poor mechanical properties. Herein, to enhance the mechanical strength of supramolecular hydrogels, agarose(AG) was incorporated into the low molecular weight hydrogelator( G1). The results of scanning electron microscopy(SEM), circular dichroism(CD) and Fourier transform infrared spectroscopy(FTIR) prove that G1 gelators can self-assemble into cross-linked network together with AG. The mechanical properties of the gels are characterized by a rotary rheometer and the mechanical properties of the hybrid hydrogels(Hgel) can be significantly improved and may be further tuned by changing the ratio of the two components. For example, the elastic modulus of Hgel II[ m (G1): m (AG)=7:3] is about 2 times higher than that of G1 hydrogel. The results demonstrate that the mechanical property of hybrid supramolecular hydrogels can be adjusted through the formation of a cross-linked network.
研究领域:
材料科学
·
高分子化学
·
生物物理学
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DOI
高影响因子
危险品化学品经营许可证（带存储）