Synthesis of Novel Biomimetic Zwitterionic Phosphorylcholine‐Bound Chitosan Derivative

Zeng, Rong; Fu, Hua; Zhao, Yufen

doi:10.1002/marc.200500876

Cited by 28 publications

(15 citation statements)

References 17 publications

(15 reference statements)

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“…Intermediate protection of the anionic group as ester and its post-polymerization cleavage to liberate the anionic site has also proven to be the most convenient strategy for preparing polymeric ammoniophosphates, ammoniophosphonates and ammoniophosphinates [63,64,153,[404][405][406][407].…”

Section: P-51mentioning

confidence: 99%

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Structures and Synthesis of Zwitterionic Polymers

2014

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Abstract:The structures and synthesis of polyzwitterions ("polybetaines") are reviewed, emphasizing the literature of the past decade. Particular attention is given to the general challenges faced, and to successful strategies to obtain polymers with a true balance of permanent cationic and anionic groups, thus resulting in an overall zero charge. Also, the progress due to applying new methodologies from general polymer synthesis, such as controlled polymerization methods or the use of "click" chemical reactions is presented. Furthermore, the emerging topic of responsive ("smart") polyzwitterions is addressed. The considerations and critical discussions are illustrated by typical examples.

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Section: P-51mentioning

confidence: 99%

“…Figure 15. Zwitterionic chitosane derivative made via Atherton-Todd reaction [404,405]. Figure 15 exemplifies the options to convert natural polymers, such as polysaccharides, into zwitterionic species.…”

Section: P-52mentioning

confidence: 99%

Structures and Synthesis of Zwitterionic Polymers

2014

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“…Cs‐ g ‐PC was synthesized according to Zeng et al Briefly, choline chloride (0.29 g, 2.1 mmol) was added to diphenyl phosphate (0.19 mL, 1.0 mmol) dissolved in distilled pyridine/dimethylsulfoxide (DMSO) (1:10, 10 mL) at room temperature, followed by stirring for 2 h. The crude product of dicholinyl H‐phosphonate dichloride (6) was obtained after evaporating the solvents. Then compound 6 was dissolved in 2‐propanol (10 mL) and added drop‐wise to compound 4 (0.32 g, ca.…”

Section: Methodsmentioning

confidence: 99%

Chitosan Grafted with Phosphorylcholine and Macrocyclic Polyamine as an Effective Gene Delivery Vector: Preparation, Characterization and In Vitro Transfection

Zhao

et al. 2015

Macromolecular Bioscience

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Herein, an effective gene delivery vector phosphorylcholine and macrocyclic polyamine grafted chitosan (PC-g(6)-Cs-g(2)-Cyclen) was developed. Chemical characterization of product PC-g(6)-Cs-g(2)-Cyclen was performed by NMR, FT-IR, gel permeation chromatography (GPC), and X-ray photoelectron spectroscopy (XPS) analysis. PC-g(6)-Cs-g(2)-Cyclen could more efficiently bind and protect plasmid DNA than macrocyclic polyamine grafted chitosan (Cs-g-Cyclen) and phosphorylcholine grafted chitosan (Cs-g-PC), as evaluated by agarose gel electrophoresis, circular dichroism spectra, and fluorescence quenching assays. PC-g(6)-Cs-g(2)-Cyclen could wrap DNA into uniform nanoparticles in the size of 112.6 ± 8.5 nm and possessed net cationic charge. UV spectroscopy and MTT assays showed excellent water-solubility and cell viability for PC-g(6)-Cs-g(2)-Cyclen. In addition, three polymer/DNA complexes showed 5.1-15.1-fold greater uptake activity and 10-14-fold higher transfection efficiency in 293 T cells as compared to chitosan/DNA complex, in which PC-g(6)-Cs-g(2)-Cyclen demonstrated the highest transfection activity. These date demonstrated that PC-g(6)-Cs-g(2)-Cyclen is a promising vector candidate for gene delivery.

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“…The synthesis of zwitterionic derivatives of CH has been devised with different procedures, such as conjugation with succinic anhydride, the reaction with 2‐chloro‐2‐oxo‐1,3,2‐dioxaphospholane, the Atherton–Todd reaction with dicholinyl phosphite dichloride, the Michael addition reaction of 2‐methacryloyloxyethyl phosphorylcholine, and the reductive amination reaction …”

Section: Introductionmentioning

confidence: 99%

“…12,13 zwitterionic groups provides a highly hydrated layer to nanoparticles and interfaces; this improves the biocompatibility of nanodevices and surfaces. 21 The synthesis of zwitterionic derivatives of CH has been devised with different procedures, such as conjugation with succinic anhydride, [22][23][24] the reaction with 2-chloro-2-oxo-1,3,2dioxaphospholane, 25 the Atherton-Todd reaction with dicholinyl phosphite dichloride, 26 the Michael addition reaction of 2methacryloyloxyethyl phosphorylcholine, 27,28 and the reductive amination reaction. 29 Zwitterionic derivatives of CH have been exploited as possible carriers for antitumor drugs, such as camptotecin 30 and doxorubicin, 31 but studies focusing on the effect of composition on the self-assembly behavior have been limited.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and self‐assembly study of zwitterionic amphiphilic derivatives of chitosan

Barbosa

Lima

Taboga

et al. 2016

J of Applied Polymer Sci

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New zwitterionic derivatives of chitosan (CH) were synthesized through the Michael addition reaction of 1‐(3‐sulfopropyl)‐2‐vinylpyridine hydroxide (SPP) with primary amines of deacetylated CHs (with weight‐average molecular weights of 46 and 216 kDa) to obtain SPP‐substituted CHs. The hydrophilic derivatives were subsequently modified with 2.1, 4.6, and 9.7% of dodecyl groups [degree of substitution by dodecyl groups (DSDod)]. The SPP‐substituted CH derivatives were characterized by 1H‐NMR, Fourier transform infrared spectroscopy, and gel permeation chromatography. Aqueous solutions of SPP‐substituted CH samples remained clear, independently of the pH (3.0 < pH < 12.0). The self‐association study of the amphiphilic derivatives was performed in aqueous buffered solution at pH 5.0 and 7.4, and the critical aggregation concentration values varied from 5.6 × 10−3 to 0.02 g/L. The measurements of dynamic light scattering and ζ potentials showed that the self‐assembly behavior was dependent on the pH and DSDod. At pH 7.4, the measured ζ potentials were near zero, and colloidal stability was provided by the hydrated zwitterionic shell of the aggregates. Transmission electron microscopy revealed spherelike microsized particles of broad distribution. The amphiphilic SPP‐substituted CH samples were shown to be nontoxic with a 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide assay performed with HeLa cells. The remarkable water solubility and nontoxicity displayed by the new SPP‐substituted CH derivatives showed promising properties for the design of CH‐based biomaterials and nanoparticles. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016, 133, 44176.

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Synthesis of Novel Biomimetic Zwitterionic Phosphorylcholine‐Bound Chitosan Derivative

Cited by 28 publications

References 17 publications

Structures and Synthesis of Zwitterionic Polymers

Structures and Synthesis of Zwitterionic Polymers

Chitosan Grafted with Phosphorylcholine and Macrocyclic Polyamine as an Effective Gene Delivery Vector: Preparation, Characterization and In Vitro Transfection

Synthesis and self‐assembly study of zwitterionic amphiphilic derivatives of chitosan

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