Helicobacter pylori is a gram-negative bacteria that infects almost 50% of the world’s population. It is a pathogenic agent that is responsible for causing duodenal ulcers, gastritis, and even gastric cancer. Due to the rise in antibiotic resistant bacteria, triple therapy with a combination of two antibiotics and a proton pump inhibitor is becoming ineffective at clearing H. pylori infection. In order to effectively cure H. pylori infection, a new therapeutic methodology must be developed. Bacterial glycans are an attractive target for new treatments as they are linked to pathogenesis and contain unique structures that are absent in human. This project explores the utility of metabolic oligosaccharide engineering as a means to label surface glycans of H. pylori with azides and target them with a bioorthogonal reaction partner bearing the immune-stimulant 2,4-dinitrophenyl to induce immune-mediated damage. In particular, three different methodologies were compared for covalent delivery of the DNP epitope to azide-coated H. pylori: Staudinger ligation with a phosphine-based reactive partner, strain promoted azide-alkyne cycloaddition with a dibenzoazacyclooctyne-based reactive partner, and copper catalyzed azide-alkyne cycloaddition with an alkyne-based reactive partner. The effect of immune-mediated killing associated with each delivery method will be presented.

Comparison of covalent delivery methods and their effects for immune-mediated killing of Helicobacter pylori

2019 Spring National Meeting

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