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Tuesday, April 24 • 12:00pm - 1:30pm
Synthesis And Antibacterial Evaluation Of Empetroxepin A And B And Related Analogs

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The World Health Organization recognizes antimicrobial resistance (AMR) as a global problem caused by the decreasing effectiveness of conventional antibacterial drugs. Estimates are that by 2050, 10 million lives a year would be at risk from drug-resistance infections. The Wolfe research group works to develop novel antibiotics through the isolation, extraction, and characterization of secondary metabolites produced by bacteria, and by leveraging antibiotic scaffolds provided by nature to synthesize and optimize antibacterial activity through medicinal chemistry techniques. Empetroxepin A and B, isolated from the black crowberry tree, Empetrum nigrum L. (Ericaceae), exhibited weak antimycobacterial activity against M. tuberculosis H37Ra (MIC = 100 µg/mL, IC50 =25.7 µg/mL and IC50 = 28.5 µg/mL) and selectivity against human embryonic kidney 293 cells (IC50 45.6 µg/mL and IC50 96.7 µg/mL). Although this activity is modest, sufficient structural similarities exist with known bioactive molecules such as depsidone, flavin, and chalcone, suggesting that activity might be enhanced through modifications to the empetroxepin core. Prior research resulted in a synthetic strategy for both empetroxepin analogs by forming an alkene bridge between a triphenylphosphate salt and a trimethylsilane (TMS) protected salicylaldehyde followed by cyclization using potassium carbonate and a copper oxide catalyst . This research investigates the effect of new ligands to the empetroxepin core by introducing commercially available substituted salicylaldehydes chosen for their influence on steric and electrochemical properties. Each empetroxepin analog will be tested for antibacterial activity against a panel of two Gram-positive (S. aureus and B. subtilis) and two Gram-negative (E. coli and P. aeruginosa) bacteria.


Tuesday April 24, 2018 12:00pm - 1:30pm PDT
Sherrill Center Concourse