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.
journal_name
ChemMedChemjournal_title
ChemMedChemauthors
Yeoh YQ,Horsley JR,Yu J,Polyak SW,Jovcevski B,Abell ADdoi
10.1002/cmdc.202000280subject
Has Abstractpub_date
2020-08-19 00:00:00pages
1505-1508issue
16eissn
1860-7179issn
1860-7187journal_volume
15pub_type
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