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• W1976468424 endingPage "1971" @default.
• W1976468424 startingPage "1965" @default.
• W1976468424 abstract "A novel four-step method is presented to synthesize partially thiolated trimethylated chitosan (TMC) with a tailorable degree of quaternization and thiolation. First, chitosan was partially N-carboxylated with glyoxylic acid and sodium borohydride. Next, the remaining amines were quantitatively dimethylated with formaldehyde and sodium borohydride and then quaternized with iodomethane in NMP. Subsequently, these partially carboxylated TMCs dissolved in water were reacted with cystamine at pH 5.5 using EDC as coupling agent. After addition of DTT and dialysis, thiolated TMCs were obtained, varying in degree of quaternization (25−54%) and degree of thiolation (5−7%), as determined with 1H NMR and Ellman’s assay. Gel permeation chromatography with light scattering detection indicated limited intermolecular cross-linking. All thiolated TMCs showed rapid oxidation to yield disulfide cross-linked TMC at pH 7.4, while the thiolated polymers were rather stable at pH 4.0. When Calu-3 cells were used, XTT and LDH cell viability tests showed a slight reduction in cytotoxicity for thiolated TMCs as compared to the nonthiolated polymers with similar DQs. Positively charged nanoparticles loaded with fluorescently labeled ovalbumin were made from thiolated TMCs and thiolated hyaluronic acid. The stability of these particles was confirmed in 0.8 M NaCl, in contrast to particles made from nonthiolated polymers that dissociated under these conditions, demonstrating that the particles were held together by intermolecular disulfide bonds." @default.
• W1976468424 created "2016-06-24" @default.
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• W1976468424 creator A5075387713 @default.
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• W1976468424 date "2010-06-28" @default.
• W1976468424 modified "2023-10-17" @default.
• W1976468424 title "Tailorable Thiolated Trimethyl Chitosans for Covalently Stabilized Nanoparticles" @default.
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• W1976468424 doi "https://doi.org/10.1021/bm1002784" @default.
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