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chemically-modified functional Ad hybrid is thus expected to be an efficient tool for thedevelopment of gene transfer therapy.Table 1. Transduction efficiency of R8GC-Ad and WT-Ad into A549 and B16BL6 cellsB16BL6 (CAR-negative)Luciferase activity (RLU/well)A549 (CAR-positive)WT-Ad 7.8 x 10 5 3.6 x 10 8R8-GC-Ad 2.4 x 10 7 8.2 x 10 7Table 2. Transduction efficiency of ProrGC-Ad and WT-Ad into A549 and B16BL6 cellsB16BL6 (CAR-negative)Luciferase activity (RLU/well)A549 (CAR-positive)WT-Ad 3.0 x 10 5 3.6 x 10 8Pro-pep-GC-Ad 6.1 x 10 6 1.4 x 10 6In summary, we prepared peptides (R8-GC-NH 2 and Pro-pep-GC-NH 2 ) that can serve asefficient Ad transporters into CAR-negative cells (B16BL6). The chemically modified Ads,R8-GC-Ad and Pro-pep-GC-Ad, are promising tools for the development of gene transfertherapy. The modification of a viable virus with a synthetic peptide is a new field of peptidechemistry and will be a potent new resource for developing virus function.AcknowledgmentsThis work was supported in part by Grant-in-Aid for Scientific Research and by “Academic Frontier”Project for Private Universities matching fund subsidy from the Japanese Ministry of Education,Culture, Sports, Science and Technology, 2006-2010.References1. Maeda, M., Kida. S., Hojo, K., Eto, Y., Gao, J-Q., Kurachi, S., Sekiguchi, F., Mizuguchi, H.,Hayakawa, T., Mayumi, T., Nakagawa, S., Kawasaki, K. Bioog. Med. Chem. Lett. 15, 621-624(2005).2. Kida, S., Maeda, M., Hojo, K., Eto, Y., Gao, J-Q., Kurachi, S., Mizuguchi, H., Hayakawa, T.,Mayumi, T., Nakagawa, S., Kawasaki, K. Bioorg. Med. Chem. Lett. 16, 743-745(2006).3. Fernandez-Carneado, J., Kogan, M.J., Castel, S., Giralt, E. Angew. Chem. Int. Ed. Engl. 43, 1811-1814 (2004).4. Fernandez-Carneado, J., Kogan, M.J., Pujals, S., Lopez-Iglesias, C., Heitz, F., Giralt, E., J. PeptideRes. 65, 580-590 (2005).5. Futaki, S., Suzuki, T., Ohashi, W., Yagami, T., Tanaka, S., Ueda, K., Sugiura, Y. J. Biol. Chem.276, 5836-5840 (2001).375
<strong>Proceedings</strong> of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010Jelleine-I Analogues with Improved Antibacterial ActivityPaul R. HansenIGM-Bioorganic Chemistry, Faculty of Life Sciences, University of Copenhagen, DenmarkIntroductionJelleine-I (Figure 1) is an octapeptide amide, H-PFKLSLHL-NH 2 (1) isolated from RoyalJelly of honeybees (Apis mellifera) [1]. The peptide is active against Gram-positive andGram-negative bacteria. However, Jelleine-I is also hemolytic towards human erythrocytes.In the present paper, we report the synthesis and antibacterial activity of 21 analogues ofJelleine I including an Ala-scan and single residue substitutions.Results and DiscussionThe peptides were synthesized using standard Fmoc chemistry, on a TentaGel RAM resin(50 mg, loading 0.24 mmol/g). Activation of the Fmoc amino acids and formation ofpeptide bonds were carried out using DIC and HOBt. All Fmoc amino acids and couplingreagents were used in fourfold excess. Fmoc deprotection was ac<strong>com</strong>plished by treatmentwith 20% piperidine in NMP (1 x 3 min and 1 x 7 minutes). The peptides were cleavedfrom the solid support along with the permanent side chain protection groups usingTFA/H 2 O/TIS/thioanisole (90:5:2.5:2.5: v/v). The crude peptides were purified bypreparative HPLC and characterized by MALDI-TOF-MS. A stock peptide solution in 1%DMSO was prepared and the concentration was determined by amino acid analysis. Thepeptides were tested against the American Type Culture Collection (ATCC) S. aureusATCC 25923 and E. coli ATCC 25922. The MIC of each peptide was determined using amicrotitre broth dilution assay modified from the method of Hancock [2]. Briefly, serialtwofold dilutions of the peptides were made in solutions of 0.2% bovine serum albuminand 0.01% acetic acid in 96-well polypropylene microtiter plates in volumes of 50 µL.To each well was added 50 µL of the test organism in Mueller Hinton Broth to a finalconcentration of approximately 2×10 5 CFU/mL. The plates were incubated overnight at37°C and the MIC of each peptide was read as the lowest concentration of peptide thatinhibited visible growth of the organism. All MIC determinations were performed induplicate, and are the average of three independent determinations.Freshly drawn human erythrocytes in citrate-dextrose-phosphate (CDP) buffer, fromCopenhagen University Hospital were used to determine the hemolytic activity as describedby Ryge and Hansen [3].Alanine positional scanning showed restrictions on 6 out of the 8 residues (data notshown), and a moderate drop in MIC-activity for the [Ala 1 ] and [Ala 5 ] Jelleine-I analogues(Table 1).Based on the above results, two series of analogues were designed and tested. Pro 1was replaced with either Ala or 3-(2 naphthyl)-L-alanine (X) and Ser 5 was replaced withAsn or one of the more hydrophobic amino acids Val, Leu, Ile, Trp, Phe. The MICsobtained for the Jelleine-I analogues are listed in Table 1.Fig. 1. Helical wheel of Jelleine-I.376
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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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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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