Design, synthesis, and biological evaluation of cyclic peptidotriazoles derived from BPC194 as novel agents for plant protection. Issue 3 (May 2017)

• Record Type: Journal Article
• Authors: Güell, Imma; Vilà, Sílvia; Badosa, Esther; Montesinos, Emilio; Feliu, Lidia; Planas, Marta
• Is Part Of: Biopolymers. Volume 108:Issue 3(2017)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2017-05
• Subjects: antimicrobial peptides -- click chemistry -- eukaryotic cytotoxicity -- peptidomimetics -- phytopathogenic bacteria; Biopolymers -- Periodicals; Peptides -- Periodicals; Spectrum analysis -- Periodicals; 572.33
• DOI: 10.1002/bip.23012
• Languages: English
• ISSNs: 0006-3525

Abstract

Abstract: The search for novel antimicrobial agents to be used for plant protection has prompted us to design analogues incorporating non‐natural amino acids. Herein, we designed and synthesized cyclic peptidotriazoles derived from the lead antimicrobial cyclic peptide c(Lys‐Lys‐Leu 3 ‐Lys‐Lys 5 ‐Phe‐Lys‐Lys‐Leu‐Gln) (BPC194 ). In particular, Leu 3 and Lys 5 were replaced by a triazolyl alanine, a triazolyl norleucine or a triazolyl lysine. These peptides were screened for their antibacterial activity against Xanthomonas axonopodis pv. vesicatoria, Erwinia amylovora, and Pseudomonas syringae pv. syringae, for their hemolysis and for their phytotoxicity. Results showed that the type of triazolyl amino acid and the substituent present at the triazole influenced the antibacterial and hemolytic activities. Moreover, the position of this residue was also crucial for the hemolysis. The lead compoundsBPC548 andBPC550 exhibited high antibacterial activity (MIC of 3.1 to 25 μM), low hemolysis (19 and 26% at 375 μM, respectively) and low phytotoxicity. Therefore, these analogues could be used as new leads for the development of effective agents to control pathogenic bacteria responsible for plant diseases of economic importance.