Helicobacter pylori (Hp) is a pathogenic bacterium that causes ulcers and gastric cancer in humans. We set out to develop an antibiotic strategy based on unique glycans present on Hp through a three component therapeutic process � 1) metabolic labeling of Hp's glycans with the substrate peracetylated N-azidoacetylglucosamine, 2) selective targeting of azide-labeled glycans via the Staudinger ligation with  phosphine conjugated to a photosensitizer that produces reactive oxygen species in the presence of light, 3) killing phosphine-photosensitizer labeled Hp with light. We have synthesized several phosphine-photosensitizer conjugates via Fmoc-based solid phase peptide synthesis. We then assessed the ability of the conjugates to bind to azide-labeled Hp and catalyze damage in the presence of light.

Photodynamic therapy of the gastric pathogen <i>Helicobacter pylori</i> via phosphine probes delivered to surface glycans

247th National Meeting (2014)

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Photodynamic therapy of the gastric pathogen Helicobacter pylori via phosphine probes delivered to surface glycans