We have synthesised short analogues of the marine antimicrobial peptide Turgencin A from the colonial Arctic ascidian In this study, we focused on a central, cationic 12-residue Cys-Cys loop region within the sequence. Modified (tryptophan- and arginine-enriched) linear peptides were compared with Cys-Cys cyclic derivatives, and both linear and Cys-cyclic peptides were N-terminally acylated with octanoic acid (C), decanoic acid (C) or dodecanoic acid (C). The highest antimicrobial potency was achieved by introducing dodecanoic acid to a cyclic Turgencin A analogue with low intrinsic hydrophobicity, and by introducing octanoic acid to a cyclic analogue displaying a higher intrinsic hydrophobicity. Among all tested synthetic Turgencin A lipopeptide analogues, the most promising candidates regarding both antimicrobial and haemolytic activity were and . These optimized cyclic lipopeptides displayed minimum inhibitory concentrations of 4 µg/mL against , and the fungus sp. Mode of action studies on bacteria showed a rapid membrane disruption and bactericidal effect of the cyclic lipopeptides. Haemolytic activity against human erythrocytes was low, indicating favorable selective targeting of bacterial cells.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9696794PMC
http://dx.doi.org/10.3390/ijms232213844DOI Listing

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