title: Selective Uptake of a Fructose Glycopolymer Prepared by RAFT Polymerization into Human Breast Cancer Cells.
abstract: A new methacrylic fructose glycomonomer is synthesized and copolymerized with N-isopropyl acrylamide by reversible addition fragmentation chain transfer (RAFT) poly-merization. By additional copolymerization of the analog mannose, glucose, and galactose glycomonomers, a set of glycopolymers is obtained which vary in the type of sugar attached to the polyacrylamide backbone. The glycopolymers are subsequently deprotected and characterized by size exclusion chromatography, FT-IR and NMR spectroscopy, elemental analysis, as well as turbidimetry, revealing the thermoresponsive character of all synthesized glycopolymers. The deprotected glycopolymers are subsequently labeled with a Rhodamine B derivative, utilizing the thiol-functionalities derived from the RAFT endgroups. As concluded from the ArlamaBlue assay, the glycopolymers are not cytotoxic. Finally, cellular uptake studies reveal a higher uptake of the fructose polymer into MDA-MB-231 breast cancer cells compared to the other glycopolymers, which demonstrates the high potential of fructosylated polymers for potential applications in the targeted treatment of breast cancer.
authors.affiliation: Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstraße 10, 07743, Jena, Germany.|Jena Center for Soft Matter (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, 07743, Jena, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: von der Ehe
authors.affiliation: Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstraße 10, 07743, Jena, Germany.|Jena Center for Soft Matter (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, 07743, Jena, Germany.
authors.forename: Alexandra
authors.initials: A
authors.lastname: Rinkenauer
authors.affiliation: Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstraße 10, 07743, Jena, Germany.|Jena Center for Soft Matter (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, 07743, Jena, Germany.
authors.forename: Christine
authors.initials: C
authors.lastname: Weber
authors.affiliation: Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstraße 10, 07743, Jena, Germany.
authors.forename: David
authors.initials: D
authors.lastname: Szamosvari
authors.affiliation: Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstraße 10, 07743, Jena, Germany.|Jena Center for Soft Matter (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, 07743, Jena, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Gottschaldt
authors.affiliation: Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstraße 10, 07743, Jena, Germany.|Jena Center for Soft Matter (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, 07743, Jena, Germany.|Dutch Polymer Institute (DPI), P.O. Box 902, 5600, AX, Eindhoven, The Netherlands.
authors.forename: Ulrich S
authors.initials: US
authors.lastname: Schubert
mesh_terms: D000178:Acrylamides / Q000737:chemistry*; D000818:Animals; D001692:Biological Transport; D002460:Cell Line; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D005347:Fibroblasts / Q000166:cytology / Q000187:drug effects; D005632:Fructose / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006001:Glycoconjugates / Q000737:chemistry; D006801:Humans; D008358:Mannose / Q000737:chemistry; D008689:Methacrylates / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D051379:Mice; D058105:Polymerization; D012235:Rhodamines / Q000737:chemistry; D013696:Temperature
chemical_list: D000178:Acrylamides; D006001:Glycoconjugates; D008689:Methacrylates; D012235:Rhodamines; D005632:Fructose; C067295:N-isopropylacrylamide; D005947:Glucose; C029773:rhodamine B; D008358:Mannose; D005690:Galactose
keywords: RAFT polymerization; cell-uptake; fructose; glycopolymer