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Fig. 1. Phase contrast images of GUVs composed by POPG/POPC (1:1) in the presence of(A) gomesin (A4) after t.480 s; (B) magainin II,(B4) after t.675 s; (C) protegrin I, (C4)after t.973 s; (D) polyphemusin II, (D4) after t.835 s; (E) tachyplesin I, (E4) after t.778 s.The snapshots in columns 1 and 2 were taken with a 20x objective and those in columns 3and 4 were taken with a 63x objective.Although magainin II and protegrin I strongly interacted with phospholipid vesicles andinduced leakage, their mechanism of action was different and could be discerned withoptical microscopy of giant vesicles. We conclude that gomesin, polyphemusin II andtachyplesin I act via the carpet model, whereas magainin II and protegrin I form toroidal orbarrel pores. Consequently, studies with GUVs provide an easy way of testing the potentialantimicrobial activities of several lead compounds.AcknowledgmentsThe work was supported by FADA-UNIFESP, FAPESP, CNPq and CAPES.References1. Miranda, A., et al. J. Med. Chem. 37, 1450-1459 (1994).2. Angelova, M.I., et al. Faraday Discuss. 81, 303-311 (1986).3. Domingues, T.M., et al. Langmuir 26, 11077-11084 (2010).4. Silva, P.I., et al. J. Biol. Chem. 275, 33464-33470 (2000).5. Powers, J.P., et al. Biochim Biophys Acta 1698, 239-250 (2004).6. Kawano, K., et al. J. Biol. Chem. 265, 15365-15367 (1990).7. Zasloff, M., et al. Proc. Natl. Acad. Sci. 84, 5449-5453 (1987).8. Aumelas, A., et al. Eur. J. Biochem. 237, 575-583 (1996).405
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010Lasiocepsin: Novel Antimicrobial Peptide from the Venom ofEusocial Bee Lasioglossum laticepsLenka Monincová, Jiřina Slaninová, Vladimír Fučík,Oldřich Hovorka, Zdeněk Voburka, Lucie Bednárová, PetrMaloň, and Václav ČeřovskýInstitute of Organic Chemistry and Biochemistry, Academy of Sciences of the CzechRepublic, Flemingovo nám. 2, Prague 6, 166 10, Czech RepublicIntroductionWe have already shown that the venom of wild bees is a rich source of pharmacologicallyinteresting antimicrobial peptides (AMPs). As an example, three linear α-helical AMPsnamed lasioglossins (LL-I, LL-II and LL-III) were identified by us in the venom of the wildeusocial bee Lasioglossum laticeps [1]. Further detailed inspection of the venom extractrevealed the presence of other interesting AMPs. One of those, which we namedlasiocepsin (LAS), is a 27 amino acid residue peptide containing two intramoleculardisulfide bridges (Figure 1). Here we describe its isolation, synthesis, structurecharacterization and biological activities.Results and DiscussionBee specimens of Lasioglossum laticeps were collected in front of our institute in Prague inJune 2009. The venom reservoirs of 10 individuals were removed by dissection and theircontents extracted with a mixture (25 μl) of acetonitrile/water (1:1) containing 0.5% TFA.The extract was fractioned by RP-HPLC (Figure 2). Thecomponents of the peaks detected at 220 nm were analyzedby mass spectrometry and tested for the presence ofantimicrobial activity against Micrococcus luteus (Figure 2,inset). The anti-M. luteus active peptides were subjected toEdman degradation. Three peaks (24, 28 and 29)corresponded to the recently identified lasioglossins (LL-I,LL-II and LL-III) [1]. Two peptides (20, 23), showedsequence and structure similarities to lasioglossins (LL-IVand LL-V). The peptide of the peak numbered 22 showed asignificantly different sequence. We named this peptidelasiocepsin (LAS) and it became the object of our study.Fig. 1. Primary sequenceof Lasiocepsin.mAU250200150100#23LL-V#24#22LL-I #28LASLL-II#20LL-IV#29LL-III#29#20#22 #23 #24#2850010 15 20 25 30 35 40 45 50 55 60t R minFig. 2. RP-HPLC profile of Lasioglossum laticeps venom extract at 220 nm on Vydac C-18 column (205 x 4.6 mm). An elution gradient of solvent from 5% to 70% ofacetonitrile/water/0.1% TFA was applied for 60 min at 1 ml/min flow rate. Inset: Anti-M.luteus activity (clear zones in the drop diffusion test) of individual fractions delineated inthe profile.406
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Peptides 2010Tales of PeptidesProce
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Peptides 2010Tales of PeptidesProce
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IntroductionWe had the distinct hon
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Scientific programIn planning the 3
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31 st EUROPEAN PEPTIDE SYMPOSIUMSep
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published by John Wiley & Sons as a
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The Josef Rudinger AwardThis award
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Young Investigators' SymposiumThe y
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xxiv
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Design of Peptidyl-Inhibitors for G
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Synthetic Antifreeze Glycopeptide A
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Synthesis and Oxidative Folding of
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Convergent Syntheses of Huprp106-12
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Bactericidal Activity of Small Beta
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Bradykinin Analogues Acylated on Th
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Antimicrobial Activity of Small 3-(
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Interaction of Curcumin with A-Synu
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Fluorescent and Luminescent Fusion
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Cellular Expression of the Human An
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2D IR Spectroscopy of Oligopeptides
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large, non-redundant subset of prot
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The aberrantly glucosylated peptide
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Table 1. Proline cis/trans ratios o
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Table 1. Yields, UV-vis absorption
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Table 1. Purity of the targeted tri
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processes are blocked. Interestingl
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(tb4 n ,1 m )MTII(tb1 n ,4 m )MTIIF
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Fig. 2. a) Part of the 400 MHz HR-M
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Once printed, the amino acid partic
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A) PSA, few seconds73B) PSA, 45 min
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short β strands. In contrast, nume
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neg. control Cs9-Rhd MM-218Fig. 2.
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Table 1. The general structure of t
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% ID in the liver 1 h p.i.100908070
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Peptidyl phosphoranes were first re
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obtained from the same sardines and
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MccJ25 variants were produced by si
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Fig. 2. Proposed signaling mechanis
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Table 1. mCD4-HS12 antiviral activi
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Proceedings of the 31 st European P
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Subject index(S)-2-(1-adamantyl)gly
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chip 18chiral triazine condensing r
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heat stress 348helical conformation
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O-acyl isopeptide method 112obesity
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SH2-ligands 210short collagen-relat
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Author indexAboye, Teshome Leta 142
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Chi, Hongfang 480Chiche, Laurent 6C
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Geronikaki, Athina 444Gessmann, Ren
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Kostova, Kalina 528Kotzia, Georgia
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Nagata, Koji 162Nagayev, Igor Yu. 5
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Salvarese, Nicola 518Sammet, Benedi
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Vauquelin, Georges 138Veiga, Ana Sa
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