Brocazines are natural products bearing a disulfide diketopiperazine core that was isolated by Meng et al in 2004 from an endophytic fungus derived from the marine mangrove plant Avicennia marina named Penicillium brocae MA-231. Six different brocazines (A-F) were isolated and of those brocazine F showed a strong activity against the prostate cancer cell line DU145 (IC50 of 1.7 mM) and the lung cancer cell line NCI-H460 (IC50 of 0.89 mM). Brocazine G was isolated two-year later, and also possessed anticancer activity. Given the potent cytotoxicity of brocazine F & G and its intriguing polycyclic core structure, our lab. has devised a total synthesis route to access this compd. To be presented is our route developed to gain access to brocazine F and G, biological evaluation (as sole agents and potentiation agents), and the development of a new targeted and designed chemical screening library to be used in the further investigations of charge location as a function of gram-negative bacteria porin mediated transport.

Total synthesis of the brocazine and chemical diversification

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

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