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Type: Journal article
Title: Short photoswitchable antibacterial peptides
Author: Yeoh, Y.Q.
Horsley, J.
Yu, J.
Polyak, S.W.
Jovcevski, B.
Abell, A.D.
Citation: ChemMedChem: chemistry enabling drug discovery, 2020; 15(16):1505-1508
Publisher: Wiley
Issue Date: 2020
ISSN: 1860-7179
Statement of
Yuan Qi Yeoh, John R. Horsley, Jingxian Yu, Steven W. Polyak, Blagojce Jovcevski, and Andrew D. Abell
Abstract: Three photoswitchable tetrapeptides, based on a known synthetic antibacterial, were designed and synthesized to determine activity against Staphylococcus aureus. Each peptide contains an azobenzene photoswitch incorporated into either the N‐terminal side chain (1), C‐terminal side chain (2), or the C‐terminus (3) to allow reversible switching between cis‐ and trans‐enriched photostationary states. Biological assays revealed that the C‐terminus azobenzene (3 ) possessed the most potent antibacterial activity, with an MIC of 1 μg/mL. In this study, net positive charge, hydrophobicity, position of the azobenzene, secondary structure, and amphiphilicity were all found to contribute to antibacterial activity, with each of these factors likely facilitating the peptide to disrupt the negatively charged bacterial lipid membrane. Hence, these short photoswitchable antibacterial tetrapeptides provide insights for the future design and synthesis of antibiotics targeting S. aureus.
Keywords: Amphiphilicity; antibacterial peptides; azobenzene photoswitch; hydrophobicity; Staphylococcus aureus
Rights: © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
DOI: 10.1002/cmdc.202000280
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