Selective Uptake of a Fructose Glycopolymer Prepared by RAFT Polymerization into Human Breast Cancer Cells
详细信息 查看全文
- 作者：Christian von der Ehe ; Alexandra Rinkenauer ; Christine Weber ; David Szamosvari ; Michael Gottschaldt and Ulrich S. Schubert
- 关键词：cell-uptake ; fructose ; glycopolymer ; RAFT polymerization
- 刊名：Macromolecular Bioscience
- 出版年：2016
- 出版时间：April 2016
- 年：2016
- 卷：16
- 期：4
- 页码：508-521
- 全文大小：2026K
- ISSN：1616-5195
文摘
A new methacrylic fructose glycomonomer is synthesized and copolymerized with N-isopropyl acrylamide by reversible addition fragmentation chain transfer (RAFT) polymerization. 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.