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Synthetic Enantiopure Carbohydrate Polymers that are Highly Soluble in Water and Noncytotoxic.


ABSTRACT: The first synthesis of poly-amido-saccharides (PASs) from a galactose(gal)-derived ?-lactam sugar monomer is reported. The polymers are prepared using a controlled anionic ring-opening polymerization and characterized by NMR, optical rotation, IR, and GPC. Galactose-derived PASs display high solubility in aqueous solutions and are noncytotoxic to HepG2, CHO, and HeLa cell lines. To evaluate whether gal-derived PASs are recognized by the gal-specific lectin present on human hepatocytes, cellular uptake of rhodamine-labeled polymers is assessed using flow cytometry and fluorescence microscopy. Based on these results, the polymers are taken into cells via endocytosis that is not dependent on the gal-specific receptor on hepatocytes. Neutral, hydrophilic polymers, such as gal-derived PASs, are desirable materials for a range of biomedical applications, such as drug delivery, surface passivation, and hydrogel formation.

SUBMITTER: Dane EL 

PROVIDER: S-EPMC3932237 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Synthetic Enantiopure Carbohydrate Polymers that are Highly Soluble in Water and Noncytotoxic.

Dane Eric L EL   Chin Stacy L SL   Grinstaff Mark W MW  

ACS macro letters 20131001 10


The first synthesis of poly-amido-saccharides (PASs) from a galactose(gal)-derived β-lactam sugar monomer is reported. The polymers are prepared using a controlled anionic ring-opening polymerization and characterized by NMR, optical rotation, IR, and GPC. Galactose-derived PASs display high solubility in aqueous solutions and are noncytotoxic to HepG2, CHO, and HeLa cell lines. To evaluate whether gal-derived PASs are recognized by the gal-specific lectin present on human hepatocytes, cellular  ...[more]

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