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Significance The roseobacter constitute nearly 25% of marine bacteria in coastal areas. They have been shown to produce a potent antibiotic, tropodithietic acid (TDA), which confers far-reaching aquacultural and ecological benefits. We have examined the mode of action of TDA using a number of methods including bacterial cytological profiling. Surprisingly, TDA clusters with molecules that are structurally unrelated and highly cytotoxic. Subsequent screens demonstrate that, aside from its antibacterial activity, TDA is also a potent, broad-range, and potentially useful anticancer agent. Our studies highlight the power of profiling methods in repurposing bioactive compounds, reveal the mode of action of the unusual troponoid TDA, and uncover a previously unknown link between two metabolic cycles, which together provide TDA resistance to the producing roseobacter.

Mode of action and resistance studies unveil new roles for tropodithietic acid as an anticancer agent and the γ-glutamyl cycle as a proton sink