Tunable Nanocarrier Morphologies from Glycopolypeptide-based Amphiphilic Biocompatible Star Copolymers and Their Carbohydrate Specific Intracellular Delivery

Nano-carriers with carbohydrates on the surface represent a very interesting class of drug delivery vehicles since carbohydrates are involved in bio-molecular recognition events in vivo. We have synthesized biocompatible miktoarm star copolymers comprising glycopolypeptide and poly(ε-caprolactone) chains, using ring opening polymerization and ‘click chemistry’. The amphiphilic copolymers were self-assembled in water into morphologies such as nanorods, polymersomes and micelles with carbohydrates displayed on the surface. We demonstrate that, the formation of nanostructure could be tuned by chain length of the blocks and was not affected by the type of sugar residue. These nanostructures were characterized in detail using a variety of techniques such as TEM, AFM, cryogenic electron microscopy, spectrally resolved fluorescence imaging and dye encapsulation techniques. We show that it is possible to sequester both hydrophobic as well as hydrophilic dyes within the nanostructures. Finally, we show that these non-cytotoxic manno-sylated rods and polymersomes were selectively and efficiently taken up by MDA-MB-231 breast cancer cells demonstrating their potential as nanocarriers for drug delivery.