title: Peptidotriazoles with antimicrobial activity against bacterial and fungal plant pathogens.
abstract: We designed and prepared peptidotriazoles based on the antimicrobial peptide BP100 (LysLysLeuPheLysLysIleLeuLysTyrLeu-NH(2)) by introducing a triazole ring in the peptide backbone or onto the side chain of a selected residue. These compounds were screened for their in vitro growth inhibition of bacterial and fungal phytopathogens, and for their cytotoxic effects on eukaryotic cells and tobacco leaves. Their proteolytic susceptibility was also analyzed. The antibacterial activity and the hemolysis were influenced by the amino acid that was modified with the triazole as well as by the absence of presence of a substituent in this heterocyclic ring. We identified sequences active against the bacteria Xanthomonas axonopodis pv. vesicatoria, Erwinia amylovora, Pseudomonas syringae pv. syringae (MIC of 1.6-12.5 μM), and against the fungi Fusarium oxysporum (MIC<6.2-12.5 μM) with low hemolytic activity (0-23% at 50 μM), high stability to protease digestion and no phytotoxicity. These peptidotriazoles constitute good candidates to design new antimicrobial agents.
authors.affiliation: LIPPSO, Department of Chemistry, University of Girona, Campus Montilivi, E-17071 Girona, Spain.
authors.forename: Imma
authors.initials: I
authors.lastname: Güell
authors.forename: Lluís
authors.initials: L
authors.lastname: Micaló
authors.forename: Laura
authors.initials: L
authors.lastname: Cano
authors.forename: Esther
authors.initials: E
authors.lastname: Badosa
authors.forename: Rafael
authors.initials: R
authors.lastname: Ferre
authors.forename: Emilio
authors.initials: E
authors.lastname: Montesinos
authors.forename: Eduard
authors.initials: E
authors.lastname: Bardají
authors.forename: Lidia
authors.initials: L
authors.lastname: Feliu
authors.forename: Marta
authors.initials: M
authors.lastname: Planas
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015195:Drug Design; D004353:Drug Evaluation, Preclinical / Q000379:methods; D044084:Erwinia amylovora / Q000187:drug effects; D005670:Fusarium / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D009842:Oligopeptides / Q000737:chemistry; D044224:Pseudomonas syringae / Q000187:drug effects; D060327:Solid-Phase Synthesis Techniques; D014230:Triazoles / Q000737:chemistry; D053532:Xanthomonas axonopodis / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D009842:Oligopeptides; D014230:Triazoles; C540525:lysyl-lysyl-leucyl-phenylalanyl-lysyl-lysyl-isoleucyl-leucyl-lysyl-tyrosyl-leucinamide