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Molecules 2017, 22(11), 1817; doi:10.3390/molecules22111817

Tryptophan-Containing Cyclic Decapeptides with Activity against Plant Pathogenic Bacteria

1
LIPPSO, Departament de Química, University of Girona, Maria Aurèlia Capmany 69, 17003 Girona, Spain
2
Institut de Química Computacional i Catàlisi i Departament de Química, University of Girona, Maria Aurèlia Capmany 69, 17003 Girona, Spain
3
Laboratory of Plant Pathology, Institute of Food and Agricultural Technology-CIDSAV-XaRTA, University of Girona, Maria Aurèlia Capmany 61, 17003 Girona, Spain
*
Authors to whom correspondence should be addressed.
Received: 2 October 2017 / Revised: 25 October 2017 / Accepted: 25 October 2017 / Published: 26 October 2017
(This article belongs to the Special Issue Antimicrobial Peptides and Peptidomimetics)
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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. View Full-Text
Keywords: antimicrobial peptides; cyclopeptides; plant pathogens; hemolysis; eukaryotic cytotoxicity; antibacterial activity antimicrobial peptides; cyclopeptides; plant pathogens; hemolysis; eukaryotic cytotoxicity; antibacterial activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Camó, C.; Torné, M.; Besalú, E.; Rosés, C.; Cirac, A.D.; Moiset, G.; Badosa, E.; Bardají, E.; Montesinos, E.; Planas, M.; Feliu, L. Tryptophan-Containing Cyclic Decapeptides with Activity against Plant Pathogenic Bacteria. Molecules 2017, 22, 1817.

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