Bacterial biofilms are surface-attached bacterial communities containing enriched persister cells encased within an extracellular matrix. Biofilms are tolerant to antibiotic treatments and host responses, associated with ~80% bacterial infections and kill 550,000 people each year. Inspired by phenazine antibiotics, our group found halogenated phenazine (HP) analogues are potent biofilm-eradicating agents. Herein, we report different modular synthetic approaches to achieve diverse HPs. Initially, 1-methoxyphenazines with substitution at the 6- to 8-positions were synthesized via a Wohl-Aue reaction with commercially available anilines and nitroarenes. HPs derived from the Wohl-Aue reaction, including 6-substituted analogues demonstrated potent activities, eradicating both planktonic and biofilm bacteria. In addition, an improved Wohl-Aue route was used to enhance the synthesis of HPs, bearing new functionality at the 3-position. One new HP analogue displayed in vivo efficacy in a wound infection model in mice.

Synthesis and discovery of new halogenated phenazine antibacterial and biofilm-eradicating agents

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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