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Short Photoswitchable Antibacterial Peptides
Author(s) -
Yeoh Yuan Qi,
Horsley John R.,
Yu Jingxian,
Polyak Steven W.,
Jovcevski Blagojce,
Abell Andrew D.
Publication year - 2020
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.202000280
Subject(s) - azobenzene , photoswitch , antibacterial activity , chemistry , peptide , antibacterial peptide , side chain , amphiphile , staphylococcus aureus , stereochemistry , combinatorial chemistry , biochemistry , bacteria , organic chemistry , biology , molecule , copolymer , genetics , polymer
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 .