A pH‐Responsive Superamphiphile Based on Dynamic Covalent Bonds

Wang, Chao; Wang, Guangtong; Wang, Zhiqiang; Zhang, Xi

doi:10.1002/chem.201003502

Cited by 145 publications

(128 citation statements)

References 60 publications

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“…Comparing Figure 4 b with 4a, it can be seen that when pH changed from 7.4 to 5.0, the microcapsules became permeable, owing to the degradability by hydrolysis of the Schiff base at low pH, as reported previously. [14,32,33] Comparing Figure 4 c with 4 b, it is very interesting that in the media with the same pH, when adding 10 mm reduced DTT, the permeability increased; this effect can be attributed to the cleavage of -SÀS-within the formed multilayers, a consistent result with Ellmans analysis. Utilizing this dual sensitivity may open opportunities to ensure the capsules as the effective intracellular drug-delivery platform.…”

Section: Wwwchemeurjorgsupporting

confidence: 68%

pH‐ and Redox‐Responsive Polysaccharide‐Based Microcapsules with Autofluorescence for Biomedical Applications

Gao

Fei

Zhao

et al. 2012

Chemistry A European J

105

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Autofluorescent microcapsules were assembled by covalent cross-linking of polysaccharide alginate dialdehyde (ADA) derivative and cystamine dihydrochloride (CM) through a layer-by-layer (LBL) technique. The formulated Schiff base and disulfide bonds render capsules with pH- and redox-responsive properties for pinpointed intracellular delivery based on the physiological difference between intracellular and extracellular environments. This simple and versatile method could be extended to other polysaccharide derivatives for the fabrication of autofluorescent nano- and micromaterials with dual stimuli response for biomedical applications.

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Section: Wwwchemeurjorgsupporting

confidence: 68%

pH‐ and Redox‐Responsive Polysaccharide‐Based Microcapsules with Autofluorescence for Biomedical Applications

Gao

Fei

Zhao

et al. 2012

Chemistry A European J

105

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“…A new signal appeared at 8.4 ppm could be attributed to the protons on benzoic imine conjugate structure. 22,30 At the same time, the signals of protons on the side alkyl chain of the PLys block merged into two broad signals near 1.2-2.0 ppm. It was a typical feature of protons on polymers with restricted mobility 15,33 because of the resultant PLys/ 2-FPBA complex was relatively hydrophobic at pH 7.4.…”

Section: Characterizationsmentioning

confidence: 90%

“…3A for 2-FPBA, reaction with 1-BA and CAPE led to the complete disappearance of the signal of aldehyde protons at 9.9 ppm, indicating that all of the aldehyde groups were converted. A new signal corresponding to the protons on the benzoic imine conjugate structure appeared at 8.5 ppm, 22,30 indicating the combination between 1-BA and 2-FPBA. While in the 11 B NMR spectra in Fig.…”

Section: Characterizationsmentioning

confidence: 99%

Iminoboronate-based dual-responsive micelles via subcomponent self-assembly for hydrophilic 1,2-diol-containing drug delivery

Zhang

Liu

et al. 2017

RSC Adv.

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Amphiphilic block copolymer micelles in aqueous solution have been used extensively in delivery of hydrophobic drugs with the hydrophobic core serving as the reservoir. However, encapsulation of hydrophilic drugs by polymeric micelles with hydrophobic core is relatively difficult because of the poor interaction between them. Herein, we report a novel kind of pH/GSH dual-responsive complex micelles with a hydrophilic drug loaded, via direct subcomponent self-assembly of block copolymer poly(ethyleneglycol)-block-poly(L-lysine) (PEG-b-PLys), 2-formylbenzeneboronic acid (2-FPBA) and hydrophilic 1,2-diol-containing drugs (e.g. capecitabine (CAPE)) under physiological pH 7.4 based on the synergistic formation of an iminoboronate structure. The PEG-b-PLys/2-FPBA micelles without CAPE are well-characterized in terms of micellization mechanism, size, morphology, pH-and GSHresponsiveness. Encapsulation of CAPE by forming PEG-b-PLys/2-FPBA/CAPE complex micelles via synergistic formation of the iminoboronate structure is discussed and pH-and GSH-responsive drugrelease studies are carried out. The complex micelles are stable under physiological neutral conditions but could be destroyed in response to the stimuli of physiological acidic condition (pH 5.0) and/or glutathione (GSH) at pH 7.4. pH-and GSH-responsive drug-releases are successfully achieved. The drug-loaded complex micelles could be endocytosed by HepG2 cells and efficiently deliver hydrophilic drugs into them. This type of complex micelles could be used as a promising platform for the delivery of hydrophilic 1,2-diol-containing drugs.

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“…The supraamphiphiles can self-assemble into spherical aggregates. However, when pH changes to 6.5, which is about extracellular pH of tumour cells, the imine bonds are broken, and the superamphiphilic spherical aggregates are disassembled, releasing the encapsulated guest molecules [23]. Similar idea can also be used to fabricate oxidation responsive polymeric supra-amphiphiles by the complexation of PEG-b-PAA and selenium-containing positively charged surfactants [24].…”

Section: Polymeric Supra-amphiphilesmentioning

confidence: 99%

Macromolecular self-assembly and nanotechnology in China

Chen

Wang

et al. 2013

Phil. Trans. R. Soc. A.

Self Cite

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Macromolecular self-assembly refers to the assembly of synthetic polymers, biomacromolecules and supra-molecular polymers. Through macromolecular self-assembly, the fabrication of ordered structures at different scales, the control of the dynamic assembly process and the integrations of advanced functions can be realized. Macromolecular self-assembly and nanotechnology research in China has developed rapidly, from the early periods of follow-up at low to high level and progress into a stage of innovation and creation. This review selects some representative progresses achieved recently, aiming to reflect the current status of macromolecular self-assembly and nanotechnology research in China.

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A pH‐Responsive Superamphiphile Based on Dynamic Covalent Bonds

Cited by 145 publications

References 60 publications

pH‐ and Redox‐Responsive Polysaccharide‐Based Microcapsules with Autofluorescence for Biomedical Applications

pH‐ and Redox‐Responsive Polysaccharide‐Based Microcapsules with Autofluorescence for Biomedical Applications

Iminoboronate-based dual-responsive micelles via subcomponent self-assembly for hydrophilic 1,2-diol-containing drug delivery

Macromolecular self-assembly and nanotechnology in China

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