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Tryptophan-Containing Cyclic Decapeptides with Activity against Plant Pathogenic Bacteria.

Cristina Camó1, Maria Torné2, Emili Besalú3

  • 1LIPPSO, Departament de Química, University of Girona, Maria Aurèlia Capmany 69, 17003 Girona, Spain. cristina.camo@udg.edu.

Molecules (Basel, Switzerland)
|October 27, 2017
PubMed
Summary

New cyclic decapeptides containing tryptophan show enhanced antibacterial activity against key plant pathogens like Pseudomonas syringae and Xanthomonas axonopodis. These tryptophan-rich peptides offer a promising avenue for developing novel agricultural protection agents with low hemolytic activity.

Keywords:
antibacterial activityantimicrobial peptidescyclopeptideseukaryotic cytotoxicityhemolysisplant pathogens

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Area of Science:

  • Medicinal Chemistry
  • Agricultural Science
  • Microbiology

Background:

  • Phytopathogenic bacteria pose significant threats to crop yields and agricultural sustainability.
  • Cyclic peptides are a class of compounds with diverse biological activities, including antimicrobial properties.
  • Tryptophan (Trp) and Phenylalanine (Phe) are aromatic amino acids that can influence peptide structure and function.

Purpose of the Study:

  • To synthesize and evaluate a library of 66 cyclic decapeptides containing tryptophan (Trp) for antibacterial activity.
  • To assess the hemolytic activity of these Trp-containing peptides.
  • To compare the antibacterial efficacy of Trp analogues with previously reported Phe analogues against specific plant pathogens.

Main Methods:

  • Solid-phase synthesis of 66 cyclic decapeptides incorporating a Trp residue.
  • Screening of synthesized peptides against three key phytopathogenic bacteria: *Pseudomonas syringae* pv. *syringae*, *Xanthomonas axonopodis* pv. *vesicatoria*, and *Erwinia amylovora*.
  • Determination of minimum inhibitory concentrations (MIC) and evaluation of hemolytic activity.

Main Results:

  • The incorporation of Trp significantly improved antibacterial activity compared to Phe analogues, with 40-46 Trp analogues showing lower MIC values.
  • Specific Trp-containing peptides demonstrated potent activity: 26 peptides against *X. axonopodis* pv. *vesicatoria* (MIC 0.8–3.1 μM), 21 against *P. syringae* pv. *syringae* (MIC 1.6–6.2 μM), and six against *E. amylovora* (MIC 6.2–12.5 μM).
  • Trp derivatives generally exhibited comparable or lower hemolytic activity than Phe analogues, with 49 peptides showing ≤ 20% hemolysis at 125 μM. Peptides BPC086W and BPC108W showed excellent profiles (MIC 0.8–12.5 μM, hemolysis ≤ 8% at 125 μM).

Conclusions:

  • Tryptophan-containing cyclic decapeptides represent a promising class of compounds for combating phytopathogenic bacteria.
  • The synthesized Trp analogues exhibit potent antibacterial activity with acceptable safety profiles regarding hemolysis.
  • Selected peptides, such as BPC086W and BPC108W, are strong candidates for further development as novel agents for plant protection.