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|Title:||Photopharmacological control of cyclic antimicrobial peptides|
|Citation:||ChemBioChem: a European Journal of Chemical Biology, 2018; 19(24):2591-2597|
|Yuan Qi Yeoh, Jingxian Yu, Steven W. Polyak, JohnR.Horsley and Andrew D.Abell|
|Abstract:||Gramicidin S is a naturally occurring antimicrobial cyclic peptide. Here we present a series of cyclic peptides based on Gramicidin S each containing an azobenzene photoswitch to reversibly control secondary structure and, hence, antimicrobial activity. 1H NMR and density functional theory (DFT) calculations revealed a β-sheet/β-turn secondary structure for the cis configuration of each peptide, and an ill-defined conformation for all associated trans structures. The cis-enriched and trans-enriched photostationary states (PSS) for each of peptides 1-3 were assayed against Staphylococcus aureus (S. aureus) to reveal a clear relationship between well-defined secondary structure, amphiphilicity and optimal antimicrobial activity. Most notably, peptides 2a and 2b exhibited a four-fold difference in antimicrobial activity in the cis-enriched PSS over the trans-enriched equivalent. This photopharmacological approach allows antimicrobial activity to be regulated through photochemical control of the azobenzene photoswitch, opening new avenues in the design and synthesis of future antibiotics.|
|Keywords:||Amphiphilicity; antibiotics; photopharmacology; photoswitchable peptides; secondary structure; S. aureus|
|Rights:||© 2018 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim|
|Appears in Collections:||Medicine publications|
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