Microparticulate immunotherapy holds promise to vaccinate difficult targets like cancer. Many vehicles exist, but triggering is often based on pH or passive hydrolysis. The most effective antigen presenting cells are dendritic cells, and the lysosomes of these cells are highly oxidizing relative to acidifying. Thus, an oxidation-sensitive vehicle could enable a significant advancement in effective particulate immunotherapy. One promising class of materials being developed toward this end are aryl boronate-modified dextran polymers. The boronic esters for oxidation-sensitive materials and sensors are typically made using pinacol (Pin) as a diol. However, Pin-based aryl boronate-modified polymers are capable of transesterifying with biogenic diols, which can lead to undesirable interactions and poor material properties. To solve this, pinanediol (PD) was used in place of Pin in the synthesis of an aryl-boronate modified dextran polymer (PDB-Dex). PD’s rigid structure ensures that it forms a highly stable boronic ester. This modified dextran reverses its water solubility as desired, and improves on Pin-based materials by maintaining its solubility in organic solvents. Microparticles were prepared through single emulsion and their approximate size, measured by dynamic light scattering, was 350 ± 100 nm in diameter. Degradation of particles was triggered with hydrogen peroxide and was tracked using H-NMR and through a colorimetric assay. Preliminary biological assays and in vitro studies show low cytotoxicity and the ability to deliver an immunostimulatory agent.<br/>

Modifying dextran with stable boronic ester groups to produce an oxidation-sensitive, biocompatible polymer

2019 Spring National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.