Synthesis and characterization of novel glucose- and lactose-containing methacrylate-based radiopaque glycopolymers

Two kinds of glucose- and lactose-containing methacrylate-based radiopaque glycopolymers (MGI and MLI) were synthesized and characterized. The first glycopolymer was prepared from 2-(2′,3′,4′,6′-tetra-O-acetyl-β-d-glucosyloxy)ethyl methacrylate (AcGEMA), 2-(2′-iodobenzoyl)-ethyl methacrylate (2-IEMA) and methyl methacrylate (MMA) via bulk radical polymerization, followed by the deacetylation. The second glycopolymer was synthesized directly from 2-lactobionamidoethyl methacrylate (LAMA), 2-IEMA and MMA via radical polymerization in DMSO. The cleavage of the ester bond in 2-IEMA of MGI was determined by ¹H NMR analysis during the deacetylation. The in vitro radiopacity of these glycopolymers was demonstrated with both an X-ray detector and a CT scanner. The in vivo CT-imaging tests performed by intravenous administration of a saline solution containing the selected MLI sample in a mouse model exhibited enhanced visibility of the liver and kidney organs.