ACS Applied Materials & Interfaces
·
2023
·
IF 9.5
Siying Chen,Zhicheng Le,Jiayue Gu,Lixin Liu,Zhijia Liu,Yongming Chen
Carrier-mediated intracellular protein delivery holds tremendous application potential in biology and medicine. The ideal carrier should be well-controlled and cost-effective and able to facilitate robust delivery of diverse types of proteins into the target cells, thus ensuring efficacy in different application scenarios. Here, we describe a modular chemistry approach for generating a small-molecule amphiphile molecular library based on the Ugi four-component reaction under one-pot and mild conditions. Then, two different types of amphiphiles with the dimeric or trimeric architecture were obtained for intracellular protein delivery through in vitro screening test. Depending on the precise adjustment of the hydrophobic tails of amphiphiles, the optimized trimeric amphiphile (TA) exhibited more superior protein loading performance and a higher efficiency of delivering proteins into cells through the endocytosis pathway and subsequent endosomal escape. Furthermore, we demonstrated that the TA could be a universal delivery carrier capable of transporting broad-spectrum proteins, especially for the hard-to-deliver native antibodies, into the cytosol. Overall, we describe a robust amphiphile platform with a well-defined and cost-effective design to improve the cytosolic protein delivery capacity, exhibiting great promise for developing intracellular protein-based therapeutics.
研究领域:
化学
·
生物学
·
医学
·
药学
·
材料科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Soft Matter
·
2015
·Vol. 11
·期 20
·4075-4080
·
IF 4.029
Lijuan Shi,Fuyu Chen,Nan Sun,Liqiang Zheng
Novel gemini supra-amphiphiles, [Mim-4-Mim][DBS]2 and [Mim-4-Mim][DS]2, were facilely constructed. A slight variation of building blocks can effectively modulate the driving forces for the fabrication of gemini supra-amphiphiles, thus leading to the fine control of subsequent self-assemblies. [Mim-4-Mim][DS]2, constructed via electrostatic attraction, tends to form micelles and hexagonal liquid crystals. Rich lamellar structures, including unilamellar and multilamellar vesicles, planar bilayers, and lamellar liquid crystals can be formed by [Mim-4-Mim][DBS]2, which is constructed through electrostatic and π–π stacking interactions. With increasing temperatures, [Mim-4-Mim][DBS]2 exhibits interesting phase separation in the La phase, behaving like common nonionic surfactants. The cross-linking between vesicles, where the “bola-type” [Mim-4-Mim]2+ cations act as the bridges, was found to promote the elongation of aggregates until the occurrence of phase separation.
研究领域:
材料科学
·
化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS
·
2015
·
IF 2.752
Jiao Wang,Xiao Chen,Wanling Cui,Sijing Yi
pH-responsive vesicles have been prepared from the mixture of 1-(10-(4-formyl-phenoxy) decyl)-pyridinium (FDP) or 1-methyl-3-(10-(4-formyl-phenoxy) decyl) imidazolium (FDI) with 1-octyl amine at a molar ratio of 1:1 in alkaline aqueous solutions. Their structures and morphologies were characterized by transmission electron microscopy with sample preparations by negative staining or freeze-fracture. Basically, the spherical unilamellar vesicles were formed with the mean diameters respectively of about 71 and 107 nm for two supra-amphiphile systems, which were based on the formation of dynamic imine bonds between amine and FDP (i-FDP) or FDI (i-FDI). The loading and release studies of a fluorophore, Nile red (NR), demonstrated the capabilities of these vesicles to encapsulate NR and a rapid release at low pH environment. The vesicles from i-FDP behaved relatively more sensitive to acidic environment than those from i-FDI. The dynamic transitions of supra-amphiphiles were characterized by nuclear magnetic resonance or fluorescence emission spectroscopy measurements. A lower critical micelle concentration and a higher aldehyde conversion efficiency of i-FDI than those of i-FDP were observed. The characteristics of facile formation, fast dissociation, and switchable morphologies of studied systems should be referable for designing novel smart supra-amphiphile systems with potential applications as controlled drug delivery systems.
研究领域:
生物化学
·
材料科学
·
药物递送
✓ 已验证
产品关联
DOI
高影响因子
Soft Matter
·
2018
·Vol. 14
·期 11
·2112-2117
·
IF 3.709
Shangyang Li,Aiyou Hao,Jian Shen,Ningzhao Shang,Chun Wang
In order to fabricate a novel supra-amphiphile with multiple stimulus properties, we developed the strategy of introducing a bi-functional linker to bridge the hydrophilic and hydrophobic building blocks together, by utilizing more than one kind of interaction. We characterized the assembled structure and morphology of the supra-amphiphile using transmission electron microscopy (TEM), dynamic light scattering (DLS) and X-ray diffraction (XRD). 1H NMR and UV-vis spectroscopy studies revealed that the amphiphile was constructed by the effect of host–guest recognition and a dynamic covalent bond, which could be switched ‘‘on’’ and ‘‘off’’ via UV irradiation and pH variation stimuli, respectively. This responsiveness realized finely controllable self-assembly behaviors of the supra-amphiphile, which was thus able to encapsulate and release the drug model rhodamine B.
研究领域:
材料科学
·
化学
·
生物医学工程
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Materials Science & Engineering C-Materials for Biological Applications
·
2017
·
IF 4.164
Beibei Hu,Yue Yuan,Yun Yan,Xiaoping Zhou,Yue Li,Qiming Kan,Sanming Li
A novel bolaamphiphile surfactant N , N ′-(dodecane-1, 12-diyl) bis (2,6-diaminohexanamide) (DADL) was designed and synthesized using l -lysine and 1,12-diaminododecane as the hydrophilic and hydrophobic part, respectively. After separation and purification, the structure of the synthetic bolaamphiphile surfactant was verified by FTIR, MS and 1 H NMR. The synthetic bolaamphiphile was able to self-assemble to form vesicles. After formulation screening, vesicles loaded with 5-Fluorouracil (5-Fu) were prepared with Tween 60 and DADL by sonication and were examined by dynamic light scattering and transmission electron microscopy. Micro-FTIR was applied to investigate the conformation of the bola molecules within the vesicle membrane. The release profile of the vesicles showed a pH-sensitive and sustained release. No significant toxicity was observed in an in vitro cell viability assay. The antitumor efficacy of the 5-Fu-loaded vesicles on H 22 tumor-bearing mice was remarkably high due to the EPR effects. These results show that our novel bolaamphiphile derived from lysine has excellent potential as a pH-sensitive drug carrier.
研究领域:
药剂学
·
生物医学工程
·
肿瘤学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
ACS Omega
·
2018
·
IF 0
Cuiyun Zhou,Xuenan Feng,Rong Wang,Gengxiang Yang,Tianyu Wang,Jianzhuang Jiang
Demands related to clean energy and environmental protection promote the development of novel supramolecular assemblies for photocatalysis. Because of the distinctive aggregation behaviors, bolaamphiphiles with two hydrophilic end groups could be theoretically the right candidates for the fabrication of high-performance photocatalysis. However, photocatalytic applications based on bolaamphiphilic assemblies were still rarely investigated. Especially, the relationship between diverse assembled nanostructures and the properties for different applications is urgently needed to be studied. Herein, we demonstrate that using the hierarchical assembly of bolaamphiphiles could correctly induce the porphyrin supramolecular architectures with much better photocatalytic performances than the aggregations containing 450 times of the porphyrin molecules, even though both molecular structures as well as the J-aggregations of porphyrin building blocks are same in two different systems. Thus, the co-assembly of l-phenylalanine terminated bolaamphiphile (Bola-F) and the porphyrin containing four hydroxyl groups (tetrakis-5,10,15,20-(4-hydroxyphenyl)porphyrin) can form microtube in methanol and forms fibers/spheres in methanol/water mixture. For catalyzing the photodegradation of rhodamine B, the small amount of J-aggregated porphyrin within Bola-F microtubes show much better photocatalytic performance comparing with that of huge porphyrin J-aggregations in fibers/spheres. The supramolecular assemblies as well as the photocatalysis were thoroughly characterized by different spectroscopies and electron microscopy. It is demonstrated that the co-assembly with bolaamphiphiles could inhibit the energy transfer of porphyrin aggregation and subsequently benefit the electron transfer and corresponding photocatalysis under photo-irradiation. This work is not only useful for further understanding the hierarchically supramolecular assembly but also provides a new strategy for making novel functional supramolecular architectures based on the assembly of bolaamphiphiles and porphyrins.
研究领域:
材料科学
·
化学
·
环境科学
✓ 已验证
产品关联
DOI
PubMed
RSC Advances
·
2016
·Vol. 6
·期 57
·52189-52200
·
IF 3.289
Tao Sun,Lan Shu,Jian Shen,Chunhui Ruan,Zhifeng Zhao,Chen Jiang
Superamphiphiles are considered as a promising approach for fabricating stimuli-responsive materials. Sensitivity to more than one stimulus can improve the system's versatile performance. In this study, we proposed a facile dual-responsive vesicle constructed from Bola-type superamphiphiles. An azobenzene dimer linked by a disulfide bond was synthesized. As the guest molecule, the azobenzene dimer can be included into the β-cyclodextrin's cavity from both ends to form a novel Bola-type superamphiphile, which can further assemble into a vesicular structure in aqueous solution. The vesicles were characterized by transmission electron microscopy (TEM) and dynamic light scattering (DLS). The formation mechanism of the vesicular structure was suggested based on the NMR, Fourier transform infrared spectroscopy (FT-IR) and X-ray diffraction (XRD) results. The photo and redox responsiveness of the vesicles was studied. The vesicles were found able to carry mitomycin C (MMC) and the drug-release can be greatly promoted upon UV irradiation or reduction.
研究领域:
材料科学
·
生物化学
·
药学
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
·
2022
·
IF 6.633
Zhiyin Yao,Na Du,Nan Chen,Jianqiang Liu,Wanguo Hou
Proto-single chain amphiphiles (P-SCAs) vesicles are considered to be a plausible model of the protocell on early Earth due to their primordial relevancy and membrane structure. In this work, we selected P-SCAs sodium 2-ketooctanate (SKO) and proto-nucleobases (PNBs, including cytosine, uracil, adenine, and guanine) as the building constituents of the vesicles. The PNB molecules incorporate into SKO bilayers to form PNB@SKO vesicles with a binding rate of 7% − 12%. The interactions between them increase the solubility of PNB in water obviously while decreasing the critical vesicle concentration of SKO. The morphology, size, and membrane thickness of SKO PRB@SKO vesicles are not affected by the PNB combination significantly. A binding mechanism is proposed based on the results of Fourier transform infrared and small angle X-ray scattering. The rigid planar PNB molecules orientate via hydrogen bonding in the tilted bilayers of SKO, without excessive disruption to the membrane structure. Both ribozyme-catalyzed and non-enzymatic RNA copying reactions require high concentrations of divalent ions, fortunately, the salt resistance of these PNB@SKO vesicles is surprisingly remarkable, one or two orders of magnitude greater than the other typical P-SCAs vesicles systems. We expect that this primitively relevant vesicle system can exert its potential advantages in the proto-membrane mimicry of the origin of life.
研究领域:
生物化学
·
分子生物学
·
起源化学
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
·
2024
·
IF 5.3
Bin Liu,Meiran Liu,Zhenghao Wu,Meiyu Zhang,Fanpeng Meng,Yanlan Wang,Na Du,Huifang Xu
Protocell compartments composed of simple amphiphilic molecules could have survived on the clay mineral surfaces which can serve well as plausible sites for prebiotic chemistry on the early Earth. Herein we chose four common single-chain amphiphiles (SCAs), including the anionic surfactant sodium dodecyl sulfate (SDS) and sodium dodecylbenzenesulfonate (SDBS), the cationic surfactant dodecyltrimethylammonium bromide (DTAB) and the zwitterionic lauryl sulfobetaine (LSB)), as model constituents of early membranes to establish a tentative model for protocell compartment. Positively charged Mg 2 Al-/Mg 2 Fe-layered double hydroxides (LDHs) and FeS 2 are viewed as models of clay minerals. We demonstrate by comprehensively experimental study that unconventional vesicles can be easily promoted in a SCA aqueous micellar solution in the presence of model particles. Morphology evolutions are traced by collecting samples from mixtures of LDHs and SCA aqueous solutions and then recording at different incubation times via negative-staining or cryo-transmission electron microscopy (NS-TEM or cryo-TEM) and dynamic light scattering (DLS). Additionally, the stability of SCA bilayer membranes under possible prebiotic environment are tentatively studied. This work not only offers a robust yet versatile approach for the fabrication of novel vesicles but also provides new insights into the origin of cellular life.
研究领域:
生物化学
·
起源化学
·
地质生物学
✓ 已验证
产品关联
DOI
高影响因子
LANGMUIR
·
2021
·
IF 3.882
Qi Hao,Yuetong Kang,Jiang-Fei Xu,Xi Zhang
A novel fluorescence “turn-on” enzyme-responsive supra-amphiphile is developed based on the host–guest recognition between γ-cyclodextrin (γ-CD) and an amphiphilic tetraphenylethene-sodium glycyrrhetinate conjugate (TPE-SGA). The covalent amphiphile TPE-SGA displayed strong fluorescence in aqueous solution owing to the aggregation-induced emission. Upon addition of γ-CD, the fluorescence of TPE-SGA was effectively turned off due to the host–guest recognition with γ-CD prohibiting the aggregation of TPE-SGA in aqueous solution. The as-formed nonfluorescent supra-amphiphile (TPE-SGA/γ-CD) inherited the α-amylase-responsive property of γ-CD. In the presence of α-amylase, the fluorescence of the supra-amphiphile was gradually turned on owing to the hydrolysis of γ-CD, and the fluorescence intensity linearly correlated to the activity of α-amylase. This study enriches the field of supra-amphiphile on the basis of cyclodextrin-based host–guest chemistry and provides a novel strategy to construct fluorescence turn-on functioned self-assemblies. It is anticipated that the fluorescence turn-on supra-amphiphile has potential applications in biological analysis and diagnosis of pancreatic diseases.
研究领域:
超分子化学
·
生物分析
·
医学诊断
✓ 已验证
DOI
高影响因子
Soft Matter
·
2015
·Vol. 12
·期 4
·1192-1199
·
IF 4.029
Huixin Zou,Hongcheng Sun,Liang Wang,Linlu Zhao,Jiaxi Li,Zeyuan Dong,Quan Luo,Jiayun Xu,Junqiu Liu
Glutathione peroxidase (GPx) is a major defense against hydroperoxides as a kind of seleno-enzyme that protects cells from oxidative damage. A supramolecular vesicle with controllable GPx activity and morphology has been successfully constructed by the self-assembly of supra-amphiphiles formed by host–guest recognition between cyclodextrin and adamantane derivatives. By introducing thermosensitive poly(N-isopropylacrylamide) (PNIPAM) scaffolds and the catalytic moiety selenium into adamantane and cyclodextrin, respectively, the complex of catalysis-functionalized cyclodextrin with thermosensitivity-functionalized adamantane directed the formation of a supramolecular vesicle which acted as a GPx mimic at 37 °C. The self-assembled nanoenzyme exhibited an obvious temperature responsive characteristic and high GPx-like catalytic activity promoting the reduction of hydrogen peroxide (H2O2) with glutathione (GSH) as the reducing substrate at 37 °C. However, the vesicle disassembled when the temperature decreased to 25 °C due to the transition of PNIPAM between the coil and the globule. Interestingly, the catalytic activity changed along with the transformation of morphologies. The vesicle structure self-assembled at 37 °C provided the favorable microenvironment for the enzymatic reaction, hence we successfully developed a temperature-responsive nanoenzyme model. Moreover, the catalytic activity of the thermosensitive GPx mimic exhibited excellent reversibility and typical saturation kinetics behaviour similar to a natural enzyme catalyst. It is assumed that the proposed GPx model not only has remarkable advantages such as easy functionalization and facile preparation but also provided a new way to develop intelligent responsive materials.
研究领域:
生物化学
·
材料科学
·
仿生学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
ACS Applied Materials & Interfaces
·
2015
·
IF 6.723
Honghai Liu,Decheng Wan,Jiang Du,Ming Jin
Straightforward organization of platinum nanoparticles (PtNPs) onto a macroscopic and robust material is described. PtNPs are in situ produced and stabilized by a dendritic amphiphile, where the latter consists of a hyperbranched polyethylenimine (PEI) as core and poly(styrene-co-2-ethylhexyl acrylate (P(St-EHA)) as shell. The resulting Pt@PEI@P(St-EHA), upon mixing with biphasic water and oil (a mixture of EHA and a dimethacrylate cross-linker in toluene), can self-assemble along the water/oil (W/O) interface and result in a stable emulsion. At W/O = 80/20 (volume ratio), a high internal phase emulsion (HIPE) forms and can be radically transformed into an open-cellular and elastic monolith termed Pt-polyHIPE, with PtNPs decorated on the surface. The Pt-polyHIPE is mechanically robust, and the cross-linking homogeneity by the dimethacrylate is responsible for the strength. The Pt-polyHIPE shows an active catalytic property, as evaluated by reduction of 4-nitrophenol. The material is conveniently and well recyclable, showing no decrease in catalytic activity at least within 20 cycles. Energy-dispersive X-ray spectra and thermogravimetric analysis also support sufficient retaining of the Pt species, where the multivalent and multiligand PEI should be responsible for this property.
研究领域:
材料科学
·
化学工程
·
催化领域
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）