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Novel antimicrobial peptides from the venom of the eusocial bee Halictus sexcinctus (Hymenoptera: Halictidae) and their analogs

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Abstract

Two novel antimicrobial peptides, named halictines, were isolated from the venom of the eusocial bee Halictus sexcinctus. Their primary sequences were established by ESI-QTOF mass spectrometry, Edman degradation and enzymatic digestion as Gly-Met-Trp-Ser-Lys-Ile-Leu-Gly-His-Leu-Ile-Arg-NH2 (HAL-1), and Gly-Lys-Trp-Met-Ser-Leu-Leu-Lys–His-Ile-Leu-Lys-NH2 (HAL-2). Both peptides exhibited potent antimicrobial activity against Gram-positive and Gram-negative bacteria but also noticeable hemolytic activity. The CD spectra of HAL-1 and HAL-2 measured in the presence of trifluoroethanol or SDS showed ability to form an amphipathic α-helical secondary structure in an anisotropic environment such as bacterial cell membrane. NMR spectra of HAL-1 and HAL-2 measured in trifluoroethanol/water confirmed formation of helical conformation in both peptides with a slightly higher helical propensity in HAL-1. Altogether, we prepared 51 of HAL-1 and HAL-2 analogs to study the effect of such structural parameters as cationicity, hydrophobicity, α-helicity, amphipathicity, and truncation on antimicrobial and hemolytic activities. The potentially most promising analogs in both series are those with increased net positive charge, in which the suitable amino acid residues were replaced by Lys. This improvement basically relates to the increase of antimicrobial activity against pathogenic Pseudomonas aeruginosa and to the mitigation of hemolytic activity.

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Acknowledgments

This work was supported by the Czech Science Foundation, Grant No. 203/08/0536, and by research project no. Z40550506 of the Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic. We thank our technical assistants Mrs. Hana Hulačová and Mrs. Jitka Čermáková for the help with peptide synthesis. We also thank Gale A. Kirking at English Editorial Services, S. R .O. for assistance with the English.

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Authors and Affiliations

  1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo 2, 16610, Prague 6, Czech Republic

    Lenka Monincová, Miloš Buděšínský, Jiřina Slaninová, Oldřich Hovorka, Josef Cvačka, Zdeněk Voburka, Vladimír Fučík, Lenka Borovičková, Lucie Bednárová & Václav Čeřovský

  2. Department of Biochemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 12840, Prague 2, Czech Republic

    Lenka Monincová

  3. Department of Zoology, Faculty of Science, Charles University in Prague, Viničná 7, 12844, Prague 2, Czech Republic

    Jakub Straka

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  1. Lenka Monincová
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  3. Jiřina Slaninová
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Correspondence to Václav Čeřovský.

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Monincová, L., Buděšínský, M., Slaninová, J. et al. Novel antimicrobial peptides from the venom of the eusocial bee Halictus sexcinctus (Hymenoptera: Halictidae) and their analogs. Amino Acids 39, 763–775 (2010). https://doi.org/10.1007/s00726-010-0519-1

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