Abstract
Recent advances in polymer science are enabling substantial progress in nanobiotechnology, particularly in the design of new tools for enhanced understanding of cell biology and for smart drug delivery formulations. Herein, a range of novel galactosylated diblock copolymer nano-objects is prepared directly in concentrated aqueous solution via reversible addition–fragmentation chain transfer polymerization using polymerization-induced self-assembly. The resulting nanospheres, worm-like micelles, or vesicles interact in vitro with galectins as judged by a turbidity assay. In addition, galactosylated vesicles are highly biocompatible and allow intracellular delivery of an encapsulated molecular cargo.
Highlights
Controlled radical polymerization (CRP) techniques have enabled synthetic chemists to prepare a remarkably wide range of functional copolymers.[1]
Galectins are ubiquitous within the cell and are highly mobile; they can be found in the cytosol and nuclear region and, secretion signal peptides have not been found in the sequence of galectins, they are present in the extracellular space.[16]
A novel route to a methacrylic glycomonomer was devised. This method relies on the very high efficiency and regioselectivity offered by thia-Michael addition to acrylates.45 1-Thio-β-Dgalactose was readily prepared on a multigram scale according to literature protocols[43] and subsequently reacted with 3(acryloyloxy)-2-hydroxypropyl methacrylate to produce the desired galactose methacrylate (GalSMA) in 63% yield
Summary
Controlled radical polymerization (CRP) techniques have enabled synthetic chemists to prepare a remarkably wide range of functional copolymers.[1]. Mammalian galectins are a family of lectins that exhibit strong affinity for β-galactose-containing glycoconjugates.[14] All galectins share a core sequence consisting of about 130 amino acids, many of which are highly conserved. This core sequence is known as the carbohydrate recognition domain (CRD) and is responsible for the binding of specific sugars.[15] The biological significance of specific carbohydrate-ligand recognition by various galectins is not fully understood, but this may in part explain why individual galectins preferentially bind to different glycoprotein counterreceptors, which implies specific targeting. Galectin targeting has the potential to offer new therapeutic avenues for nanomedicine
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