Controlled synthesis and properties of Neoglycoconjugates

Abstract

Glucosyl and galactosyl bearing methacrylates were synthesised using a combination of well known carbohydrate chemistry and ultrasonic chemistry. Polymerisation of these monomers by aqueous reversible addition-fragmentation chain transfer polymerisation yielded glycosylated polymers in high yield with a high degree of control over molecular weight and narrow polydispersity. Polymers of varying levels of glycosylation could be achieved through addition of a comonomer. Block copolymers were synthesised through sequential monomer addition. Binding studies of these polymers to Ricinus communis agglutinin 120 by both isothermal titration calorimetry and surface plasmon resonance found a high degree of molecular weight dependence on avidity. Studies also suggest that the increase in avidity through multivalency is due to both simultaneous binding to multiple receptors and the increased probability of binding due to the high local concentration of ligands. Polymers synthesised have been used in the synthesis of glycosylated gold nano-particles. Some degree of control over nanoparticle size was achieved through adjustment of the gold:polymer ratio but was found to be limited. Agglutination assays show the particles display specific lectin binding but in vitro cell studies were unable to give conclusive information regarding the uptake of particles into cells.