Carbon dioxide sourced functional cyclic carbonates used to prepare macromolecular therapeutics to treat infectious disease and cancer

Abstract

High value specialty polycarbonates are employed in numerous applications, including resins for 3D additive printing, macromonomers for polyurethanes, surfactants, battery electrolytes, and degradable adhesives for medical applications. Driving the growth in use cases are the significant advancements made over the last two decades in improved methodologies for the synthesis of aliphatic carbonates as well as upcycling carbon dioxide (CO2) into high value-added materials. We have recently reported a method to transform 1,3- and 1,5-diols into functional cyclic carbonates without the use of hazardous reagents. Employment of TMEDA was shown to provide selective ring-closure to the cyclic carbonate in the presence of CO2 while minimizing oligomerization and formation of other byproducts. A series of commercial and synthetic 1,3- and 1,5-diols were employed to generate 6- and 8-membered cyclic carbonates with diverse pendant functional groups tuning polymer properties. The ability to tune these functional monomers and subsequent polymers has allowed numerous applications that include drug, gene and cell delivery as well as the use of the polymer as a stand-alone therapeutic including antimicrobials, anticancer agents and antiviral therapies packaged as either micelles, hydrogels or coacervates. Specifically, we address the multi-faceted problem of drug-resistance as well as other important concerns in disease treatment exploiting polymer science to develop novel macromolecular therapeutics for treating infectious disease and cancer.