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Tryptophan-Containing Cyclic Decapeptides with Activity against Plant Pathogenic Bacteria

A library of 66 cyclic decapeptides incorporating a Trp residue was synthesized on solid phase and screened against the phytopathogenic bacteria Pseudomonas syringae pv. syringae, Xanthomonas axonopodis pv. vesicatoria, and Erwinia amylovora. The hemolytic activity of these peptides was also evaluated. The results obtained were compared with those of a collection of Phe analogues previously reported. The analysis of the data showed that the presence of the Trp improved the antibacterial activity against these three pathogens. In particular, 40 to 46 Trp analogues displayed lower minimum inhibitory concentration (MIC) values than their corresponding Phe counterparts. Interestingly, 26 Trp-containing sequences exhibited MIC of 0.8 to 3.1 μM against X. axonopodis pv. vesicatoria, 21 peptides MIC of 1.6 to 6.2 μM against P. syringae pv. syringae and six peptides MIC of 6.2 to 12.5 μM against E. amylovora. Regarding the hemolysis, in general, Trp derivatives displayed a percentage of hemolysis comparable to that of their Phe analogues. Notably, 49 Trp-containing cyclic peptides showed a hemolysis ≤ 20% at 125 μM. The peptides with the best biological activity profile were c(LKKKLWKKLQ) (BPC086W) and c(LKKKKWLLKQ) (BPC108W), which displayed MIC values ranging from 0.8 to 12.5 μM and a hemolysis ≤ 8% at 125 μM. Therefore, it is evident that these Trp sequences constitute promising candidates for the development of new agents for use in plant protection

This work was supported by grants AGL2009-13255-C02-02/AGR, AGL2012-39880-C02-02 and AGL2015-69876-C2-2-R (MINECO/FEDER, EU)

Molecules, 2017, vol. 22, núm. 11, p.1817-1830

MDPI (Multidisciplinary Digital Publishing Institute)

Manager: Ministerio de Ciencia e Innovación (Espanya)
Ministerio de Economía y Competitividad (Espanya)
Author: Camó Marin, Cristina
Torné, Maria
Besalú i Llorà, Emili
Rosés Subirós, Cristina
Díaz i Cirac, Anna
Moiset, Gemma
Badosa Romañó, Esther
Bardají Rodríguez, Eduard
Montesinos Seguí, Emilio
Planas i Grabuleda, Marta
Feliu Soley, Lídia
Date: 2017 October 26
Abstract: A library of 66 cyclic decapeptides incorporating a Trp residue was synthesized on solid phase and screened against the phytopathogenic bacteria Pseudomonas syringae pv. syringae, Xanthomonas axonopodis pv. vesicatoria, and Erwinia amylovora. The hemolytic activity of these peptides was also evaluated. The results obtained were compared with those of a collection of Phe analogues previously reported. The analysis of the data showed that the presence of the Trp improved the antibacterial activity against these three pathogens. In particular, 40 to 46 Trp analogues displayed lower minimum inhibitory concentration (MIC) values than their corresponding Phe counterparts. Interestingly, 26 Trp-containing sequences exhibited MIC of 0.8 to 3.1 μM against X. axonopodis pv. vesicatoria, 21 peptides MIC of 1.6 to 6.2 μM against P. syringae pv. syringae and six peptides MIC of 6.2 to 12.5 μM against E. amylovora. Regarding the hemolysis, in general, Trp derivatives displayed a percentage of hemolysis comparable to that of their Phe analogues. Notably, 49 Trp-containing cyclic peptides showed a hemolysis ≤ 20% at 125 μM. The peptides with the best biological activity profile were c(LKKKLWKKLQ) (BPC086W) and c(LKKKKWLLKQ) (BPC108W), which displayed MIC values ranging from 0.8 to 12.5 μM and a hemolysis ≤ 8% at 125 μM. Therefore, it is evident that these Trp sequences constitute promising candidates for the development of new agents for use in plant protection
This work was supported by grants AGL2009-13255-C02-02/AGR, AGL2012-39880-C02-02 and AGL2015-69876-C2-2-R (MINECO/FEDER, EU)
Format: application/pdf
Citation: https://doi.org/10.3390/molecules22111817
ISSN: 1420-3049
Document access: http://hdl.handle.net/10256/14576
Language: eng
Publisher: MDPI (Multidisciplinary Digital Publishing Institute)
Collection: MICINN/PN 2010-2012/ AGL2009-13255-C02-02
MICINN/PN 2013-2015/AGL2012-39880-C02-02
MINECO/PE 2016-2018/AGL2015-69876-C2-2-R
Reproducció digital del document publicat a: https://doi.org/10.3390/molecules22111817
Articles publicats (D-Q)
Is part of: Molecules, 2017, vol. 22, núm. 11, p.1817-1830
Rights: Attribution 3.0 Spain
Rights URI: http://creativecommons.org/licenses/by/3.0/es/
Subject: Antibiòtics pèptids
Peptide antibiotics
Pèptids -- Síntesi
Peptides -- Synthesis
Antibiòtics pèptids
Peptide antibiotics
Title: Tryptophan-Containing Cyclic Decapeptides with Activity against Plant Pathogenic Bacteria
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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