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Design, synthesis and biological evaluation of cyclic peptidotriazoles derived from BPC194 as novel agents for plant protection

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-Leu3-Lys-Lys5-Phe-Lys-Lys-Leu-Gln) (BPC194). In particular, Leu3 and Lys5 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 compounds BPC548 and BPC550 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

This work was supported by the Spanish Ministerio de Economía y Competitividad (MINECO) [grant numbers AGL2009-13255-C02-02/AGR and AGL2012-39880-C02-02]

© Biopolymers.Peptide Science, 2017, vol. 108, núm. 3, p. e23012

Wiley

Manager: Ministerio de Ciencia e Innovación (Espanya)
Author: Güell Costa, Imma
Vilà Roura, Sílvia
Badosa Romañó, Esther
Montesinos Seguí, Emilio
Feliu Soley, Lídia
Planas i Grabuleda, Marta
Date: 2017 May 1
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-Leu3-Lys-Lys5-Phe-Lys-Lys-Leu-Gln) (BPC194). In particular, Leu3 and Lys5 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 compounds BPC548 and BPC550 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
This work was supported by the Spanish Ministerio de Economía y Competitividad (MINECO) [grant numbers AGL2009-13255-C02-02/AGR and AGL2012-39880-C02-02]
Format: application/pdf
Citation: 026165
ISSN: 0006-3525 (versió paper)
1097-0282 (versió electrònica)
Document access: http://hdl.handle.net/10256/13892
Language: eng
Publisher: Wiley
Collection: MICINN/PN 2010-2012/ AGL2009-13255-C02-02
MICINN/PN 2013-2015/AGL2012-39880-C02-02
Reproducció digital del document publicat a: http://dx.doi.org/10.1002/bip.23012
Articles publicats (D-Q)
Is part of: © Biopolymers.Peptide Science, 2017, vol. 108, núm. 3, p. e23012
Rights: Tots els drets reservats
Subject: Antibiòtics pèptids
Peptide antibiotics
Citotoxicitat
Toxicologie cellulaire
Bacteris fitopatògens
Title: Design, synthesis and biological evaluation of cyclic peptidotriazoles derived from BPC194 as novel agents for plant protection
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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