Selective Uptake of a Fructose Glycopolymer Prepared by RAFT Polymerization into Human Breast Cancer Cells
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von der Ehe, Christian; Rinkenauer, Alexandra; Weber, Christine; Szamosvari, David; Gottschaldt, Michael; Schubert, Ulrich S.
- 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.
- Research areas:
- Year:
- 2016
- Type of Publication:
- Article
- Journal:
- macromolecular Bioscience
- Volume:
- 16
- Number:
- 4
- Pages:
- 508 - 521
- DOI:
- 10.1002/mabi.201500346