Both naturally occurring and synthetic brominated furanones are known to inhibit biofilm formation by bacteria. However, most of the known structures are toxic to mammalian cells and the growth of bacteria. Here, based on a hypothesis of what the essential structural elements are for biofilm inhibition activities, we designed and synthesized a class of new bicyclic brominated furanones that contained only one bromide group with total control of regiochemistry. This new class of molecules exhibits significant reduction in the cytotoxicity towards bacteria growth and mammalian cells, yet retains the activity for inhibiting the biofilm formation. As biofilm formation is the source of many infectious diseases, health-related problems and industrial settings, these molecules present an opportunity for controlling biofilm formation without the issue of drug resistance. In this presentation, we will present the synthesis of bicyclic brominated furanones that have 5-, 6-, or 7-memebered rings, and their biological activity studies.

Controlling bacterial behavior by bicyclic brominated furanones with reduced toxicity

243rd National Meeting (2012)

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