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.
Subject(s)
Acrylamides/chemistry , Fructose/chemistry , Methacrylates/chemical synthesis , Animals , Biological Transport , Cell Line , Cell Line, Tumor , Cell Survival/drug effects , Fibroblasts/cytology , Fibroblasts/drug effects , Galactose/chemistry , Glucose/chemistry , Glycoconjugates/chemistry , Humans , Mannose/chemistry , Methacrylates/metabolism , Methacrylates/pharmacology , Mice , Polymerization , Rhodamines/chemistry , TemperatureABSTRACT
A highly porous cryogel is prepared and subsequently functionalized with an atom transfer radical polymerization (ATRP) initiator at the surface. Two new glycomonomers are introduced, which possess deprotected mannose as well as glucose moieties. These are copolymerized with N-isopropylacrylamide (NiPAm) from the cryogel surface, providing a highly hydrophilic porous material, which is characterized by SEM, FT-IR spectroscopy, and NMR spectroscopy. This functionalized support can be applied for affinity chromatography of whole cells owing to the high pore space and diameter. Such an application is exemplified by investigating the ability to capture Escherichia coli bacteria, revealing selective binding interactions of the bacteria with the mannose glycopolymer-functionalized cryogel surface. Thus, the presented glycopolymer-cryogel represents a promising material for affinity chromatography or enrichment of cells.
