title: Panurgines, novel antimicrobial peptides from the venom of communal bee Panurgus calcaratus (Hymenoptera: Andrenidae).
abstract: Three novel antimicrobial peptides (AMPs), named panurgines (PNGs), were isolated from the venom of the wild bee Panurgus calcaratus. The dodecapeptide of the sequence LNWGAILKHIIK-NH₂ (PNG-1) belongs to the category of α-helical amphipathic AMPs. The other two cyclic peptides containing 25 amino acid residues and two intramolecular disulfide bridges of the pattern Cys8-Cys23 and Cys11-Cys19 have almost identical sequence established as LDVKKIICVACKIXPNPACKKICPK-OH (X=K, PNG-K and X=R, PNG-R). All three peptides exhibited antimicrobial activity against Gram-positive bacteria and Gram-negative bacteria, antifungal activity, and low hemolytic activity against human erythrocytes. We prepared a series of PNG-1 analogs to study the effects of cationicity, amphipathicity, and hydrophobicity on the biological activity. Several of them exhibited improved antimicrobial potency, particularly those with increased net positive charge. The linear analogs of PNG-K and PNG-R having all Cys residues substituted by α-amino butyric acid were inactive, thus indicating the importance of disulfide bridges for the antimicrobial activity. However, the linear PNG-K with all four cysteine residues unpaired, exhibited antimicrobial activity. PNG-1 and its analogs induced a significant leakage of fluorescent dye entrapped in bacterial membrane-mimicking large unilamellar vesicles as well as in vesicles mimicking eukaryotic cell membrane. On the other hand, PNG-K and PNG-R exhibited dye-leakage activity only from vesicles mimicking bacterial cell membrane.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 16610 Prague 6, Czech Republic.
authors.forename: Sabína
authors.initials: S
authors.lastname: Čujová
authors.forename: Jiřina
authors.initials: J
authors.lastname: Slaninová
authors.forename: Lenka
authors.initials: L
authors.lastname: Monincová
authors.forename: Vladimír
authors.initials: V
authors.lastname: Fučík
authors.forename: Lucie
authors.initials: L
authors.lastname: Bednárová
authors.forename: Jitka
authors.initials: J
authors.lastname: Štokrová
authors.forename: Oldřich
authors.initials: O
authors.lastname: Hovorka
authors.forename: Zdeněk
authors.initials: Z
authors.lastname: Voburka
authors.forename: Jakub
authors.initials: J
authors.lastname: Straka
authors.forename: Václav
authors.initials: V
authors.lastname: Čeřovský
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology*; D023181:Antimicrobial Cationic Peptides / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D001514:Bee Venoms / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D006927:Hymenoptera / Q000378:metabolism; D008826:Microbial Sensitivity Tests; D020539:Sequence Analysis, Protein; D013329:Structure-Activity Relationship; D013501:Surface-Active Agents; D053835:Unilamellar Liposomes / Q000378:metabolism
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D023181:Antimicrobial Cationic Peptides; D001514:Bee Venoms; D013501:Surface-Active Agents; D053835:Unilamellar Liposomes