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Journal of Peptide Science: An Official Publication of the European Peptide Society

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https://www.readbyqxmd.com/read/28707817/evaluation-of-free-or-anchored-antimicrobial-peptides-as-candidates-for-the-prevention-of-orthopaedic-device-related-infections
#1
Francesca D'Este, Debora Oro, Gerard Boix-Lemonche, Alessandro Tossi, Barbara Skerlavaj
The prevention of implant-associated infection, one the most feared complications in orthopaedic surgery, remains a major clinical challenge and urges development of effective methods to prevent bacterial colonization of implanted devices. Alpha-helical antimicrobial peptides (AMPs) may be promising candidates in this respect due to their potent and broad-spectrum antimicrobial activity, their low tendency to elicit resistance and possible retention of efficacy in the immobilized state. The aim of this study was to evaluate the potential of five different helical AMPs, the cathelicidins BMAP-27 and BMAP-28, their (1-18) fragments and the rationally designed, artificial P19(9/G7) peptide, for the prevention of orthopaedic implant infections...
July 14, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28699258/cytotoxic-peptides-with-insulin-releasing-activities-from-skin-secretions-of-the-italian-stream-frog-rana-italica-ranidae
#2
J Michael Conlon, Vishal Musale, Samir Attoub, Maria Luisa Mangoni, Jérôme Leprince, Laurent Coquet, Thierry Jouenne, Yasser H A Abdel-Wahab, Peter R Flatt, Andrea C Rinaldi
Peptidomic analysis of norepinephrine-stimulated skin secretions from Italian stream frog Rana italica led to the purification and characterization of two host-defense peptides differing by a single amino acid residue belonging to the brevinin-1 family (brevinin-1ITa and -1ITb), a peptide belonging to the temporin family (temporin-ITa) and a component identified as prokineticin Bv8. The secretions contained relatively high concentrations of the methionine-sulphoxide forms of brevinin-1ITa and -1ITb suggesting that these peptides may have a role as antioxidants in the skin of this montane frog...
July 11, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28681413/re-evaluating-the-stability-of-comu-in-different-solvents
#3
Ashish Kumar, Yahya E Jad, Beatriz G de la Torre, Ayman El-Faham, Fernando Albericio
COMU is uronium-type coupling reagent based on OxymaPure. It showed several advantages over classical benzotriazole-based coupling reagents such as higher solubility, water-soluble byproduct, and monitoring the reaction by changing of color. Although COMU is well known to perform excellent in solution, but its hydrolytic stability in DMF limits its use in automatic peptide synthesizer. Herein, we evaluated the hydrolytic stability of COMU in γ-valerolactone (GVL), acetonitrile (ACN) and N-formylmorpholine (NFM) and compared its stability against DMF...
July 6, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28661555/cryptophycins-cytotoxic-cyclodepsipeptides-with-potential-for-tumor-targeting
#4
Christine Weiss, Eduard Figueras, Adina N Borbely, Norbert Sewald
Cryptophycins are a class of 16-membered highly cytotoxic macrocyclic depsipeptides isolated from cyanobacteria. The biological activity is based on their ability to interact with tubulin. They interfere with microtubule dynamics and prevent microtubules from forming correct mitotic spindles, which causes cell-cycle arrest and apoptosis. Their strong antiproliferative activities with 100-fold to 1000-fold potency compared with those of paclitaxel and vinblastine have been observed. Cryptophycins are highly promising drug candidates, as their biological activity is not negatively affected by P-glycoprotein, a drug efflux system commonly found in multidrug-resistant cancer cell lines and solid tumors...
June 29, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28635051/substitution-determination-of-fmoc-substituted-resins-at-different-wavelengths
#5
Stefan Eissler, Markus Kley, Dirk Bächle, Günther Loidl, Thomas Meier, Daniel Samson
In solid-phase peptide synthesis, the nominal batch size is calculated using the starting resin substitution and the mass of the starting resin. The starting resin substitution constitutes the basis for the calculation of a whole set of important process parameters, such as the number of amino acid derivative equivalents. For Fmoc-substituted resins, substitution determination is often performed by suspending the Fmoc-protected starting resin in 20% (v/v) piperidine in DMF to generate the dibenzofulvene-piperidine adduct that is quantified by ultraviolet-visible spectroscopy...
June 21, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28627122/a-biotinylated-peptide-bp21-as-a-novel-potent-anti-anaphylactic-agent-targeting-platelet-activating-factor
#6
Akira Sato, Keiichi Ebina
Platelet-activating factor (PAF) is an important mediator of anaphylaxis and is therefore an anti-anaphylactic drug target. We recently reported that synthetic N-terminally biotinylated peptides (BP4-BP29) inhibit PAF by directly interacting with PAF and its metabolite/precursor lyso-PAF. In this study, we investigated whether the biotinylated peptides can inhibit anaphylactic reactions in vivo. In mouse models of anaphylaxis, one of the peptides, BP21, markedly and dose-dependently inhibited hypothermia with a maximum dose-response within 30 min after administration, even at doses 20 times lesser than doses of the known PAF antagonist CV-3988...
June 19, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28626916/unexpected-functions-of-angiotensin-converting-enzyme-beyond-its-enzymatic-activity
#7
REVIEW
Jean Martinez
Angiotensin converting enzyme (ACE) is a well-known enzyme, largely studied for its action on hypertension, as it produces angiotensin II from angiotensin I. This paper describes two original behaviours of ACE. We showed that ACE could hydrolyse gastrin, a neuropeptide from the gastrointestinal tract, releasing the C-terminal amidated dipeptide H-Asp-Phe-NH2 . This dipeptide is believed to be involved in the gastrin-induced acid secretion in the stomach. This hypothetic mechanism of action of gastrin resulted in a strategy to rationally design gastrin receptor antagonists...
June 19, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28626925/stoichiometric-analysis-of-oligomeric-states-of-three-class-a-gpcrs-chemokine-cxcr4-dopamine-d2-and-prostaglandin-ep1-receptors-on-living-cells
#8
Kenichi Kawano, Tetsuya Yagi, Nozomu Fukada, Yoshiaki Yano, Katsumi Matsuzaki
G-protein-coupled receptors (GPCRs) form the largest family of transmembrane receptors, and their oligomerization has been suggested to be related to their functions. Despite extensive studies, their oligomeric states are highly controversial. One of the reasons is the overestimation of oligomerization by conventional methods. We recently established a stoichiometric analysis method for precisely determining the oligomeric state of membrane proteins on living cells with the combined use of the coiled-coil labeling method and a spectral imaging technique and showed that the prototypical class-A GPCR β2 -adrenergic receptor (β2 AR) did not form functional oligomers...
June 18, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28612448/visible-light-photoredox-catalyzed-desulfurization-of-thiol-and-disulfide-containing-amino-acids-and-small-peptides
#9
Myungmo Lee, Saskia Neukirchen, Chiara Cabrele, Oliver Reiser
A scalable protocol for the desulfurization of cysteine by using visible light, the photocatalyst Ir(dF(CF3 )ppy)2 (dtb-bpy)PF6 and triethylphosphite under biphasic reaction conditions has been developed. The loading of the catalyst can be as low as 0.01 mol%, which can be efficiently removed during the workup (≤0.3 ppm), giving rise to the corresponding desulfurized product in high yields. This method has been applied also to cystine, penicillamine, and reduced and oxidized glutathione. The desulfurization has been found to be pH sensitive, with an optimal pH value of 6...
June 14, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28608418/characterization-of-an-insulinotropic-peptide-from-skin-secretions-of-odorrana-andersonii
#10
Weijie Shang, Xinwang Yang, Xiaoman Ju, Yueying Xie, Yun Zhang, Wen-Hui Lee
Insulinotropic peptide agents are regarded as potential candidates for anti-diabetic treatment. In the present study, a novel insulinotropic peptide, termed OA-A1, was purified from frog skin secretions of Odorrana andersonii. Mature OA-A1 was determined to be a 1965.049 Da peptide with an amino acid sequence of LVGKLLKGAVGDVCGLLPIC, in which an intramolecular disulfide bridge was formed by two cysteine residues. At the cellular level, OA-A1 exhibited potent proliferation promoting effects on mouse-derived pancreatic β-TC-6 cells and significantly stimulated insulin release in β-TC-6 cells at a minimum concentration of 1 nM...
June 13, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28608410/pyrazole-amino-acids-hydrogen-bonding-directed-conformations-of-3-amino-1h-pyrazole-5-carboxylic-acid-residue
#11
Anna Kusakiewicz-Dawid, Monika Porada, Wioletta Ochędzan-Siodłak, Małgorzata A Broda, Maciej Bujak, Dawid Siodłak
A series of model compounds containing 3-amino-1H-pyrazole-5-carboxylic acid residue with N-terminal amide/urethane and C-terminal amide/hydrazide/ester groups were investigated by using NMR, Fourier transform infrared, and single-crystal X-ray diffraction methods, additionally supported by theoretical calculations. The studies demonstrate that the most preferred is the extended conformation with torsion angles ϕ and ψ close to ±180°. The studied 1H-pyrazole with N-terminal amide/urethane and C-terminal amide/hydrazide groups solely adopts this energetically favored conformation confirming rigidity of that structural motif...
June 13, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28585417/cyanobacterial-peptides-as-a-prototype-for-the-design-of-cathepsin-d-inhibitors
#12
Hao Xu, Keting Bao, Shuai Tang, Jing Ai, Haiyan Hu, Wei Zhang
Cathepsin D (Cath D) is overexpressed and secreted in a number of solid tumors and involved in the progress of tumor invasion, proliferation, metastasis, and apoptosis. Inhibition of Cath D is regarded as an attractive pathway for the development of novel anticancer drugs. Our previous studies revealed that tasiamide B, a cyanobacterial peptide that contained a statine-like unit, exhibited good inhibition against Cath D and other aspartic proteases. Using this natural product as prototype, we designed and synthesized three new analogs, which bear isophthalic acid fragment at the N-terminus and isobutyl amine (1), cyclopropyl amine (2), or 3-methoxybenzyl amine (3) moiety at the C-terminus...
June 6, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28580755/crabrolin-a-natural-antimicrobial-peptide-structural-properties
#13
Massimiliano Aschi, Argante Bozzi, Carla Luzi, Nadia Bouchemal, Marco Sette
A joint application of experimental and computational approaches has revealed the exceptionally high attitude of crabrolin, a 13-residue peptide with sequence FLPLILRKIVTAL-NH2 , to adopt alpha-helix conformation not only in membrane-mimicking solvents but also in the presence of a not negligible amount of water. Our study shows that this propensity essentially resides in the intrinsic thermodynamic stability of alpha-helix conformation whose kinetic stability is drastically reduced in water solvent. Our analysis suggests that this is due to two effects enhanced by water: a more local effect consisting of the demolition of intra-peptide H-bonds, essential for the alpha-helix formation, and a bulk - electrostatic - effect favoring conformational states more polar than alpha-helix...
June 5, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28580683/simple-method-to-assess-stability-of-immobilized-peptide-ligands-against-proteases
#14
Silvana L Giudicessi, María L Salum, Soledad L Saavedra, María C Martínez-Ceron, Osvaldo Cascone, Rosa Erra-Balsells, Silvia A Camperi
Although peptides are used as affinity chromatography ligands, they could be digested by proteases. Usually, peptide stability is evaluated in solution, which differs from the resin-bounded peptide behavior. Furthermore, the study of the degradation products requires purification steps before analysis. Here, we describe an easy method to assess immobilized peptide stability. Sample peptides were synthesized on hydroxymethylbenzamide-ChemMatrix resin. Peptidyl-resin beads were then incubated with solutions containing proteases...
June 5, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28543807/aromatic-interaction-mediated-inhibition-of-%C3%AE-amyloid-assembly-structures-and-cytotoxicity
#15
Hanyi Xie, Jiaxi Peng, Changliang Liu, Xiaocui Fang, Hongyang Duan, Yimin Zou, Yanlian Yang, Chen Wang
Abnormal aggregation of β-amyloid (Aβ) peptide plays an important role in the onset and progress of Alzheimer's disease (AD); hence, targeting Aβ aggregation is considered as an effective therapeutic strategy. Here, we studied the aromatic-interaction-mediated inhibitory effect of oligomeric polypeptides (K8Y8, K4Y8, K8W8) on Aβ42 fibrillization process. The polypeptides containing lysine as well as representative aromatic amino acids of tryptophan or tyrosine were found to greatly suppress the aggregation as evaluated by thioflavin T assay...
May 23, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28466607/conformational-latitude-activity-relationship-of-kppr-tetrapeptide-analogues-toward-their-ability-to-inhibit-binding-of-vascular-endothelial-growth-factor-165-to-neuropilin-1
#16
Bartlomiej Fedorczyk, Piotr F J Lipiński, Dagmara Tymecka, Anna K Puszko, Beata Wilenska, Gerard Y Perret, Aleksandra Misicka
Neuropilin-1 has been found to be overexpressed in several kinds of malignant tumors, and it is postulated that its interaction with the vascular endothelial growth factor 165 leads to progression of tumor vascularization and growth. Several analogues (KxxR) with various conformational latitudes have been synthesized and found as inhibitors of NRP-1. Detailed insight provided by molecular dynamics simulation allowed forming a clear relationship between flexibility of xx part of the molecule and its inhibitory activity...
May 3, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28466571/synthesis-of-relaxin-2-and-insulin-like-peptide-5-enabled-by-novel-tethering-and-traceless-chemical-excision
#17
Kishore Thalluri, Binbin Kou, Xu Yang, Alexander N Zaykov, John P Mayer, Vasily M Gelfanov, Fa Liu, Richard D DiMarchi
This report presents an entirely chemical, general strategy for the synthesis of relaxin-2 and insulin-like peptide 5. Historically, these two peptides have represented two of the more synthetically challenging members of the insulin superfamily. The key synthetic steps involve two sequential oxime ligations to covalently link the individual A-chain and B-chain, followed by disulfide bond formation under aqueous, redox conditions. This is followed by two chemical reactions that employ diketopiperazine cyclization-mediated cleavage and ester hydrolysis to liberate the connecting peptide and the heterodimeric product...
May 3, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28449250/self-assembly-of-peptide-boroxoles-on-cis-dihydroxylated-oligoamide-templates-in-water
#18
André Wuttke, Armin Geyer
We develop templates that can be used to stabilize consistent oligomers of a bioactive peptide. In the present study, we synthesize oligomers of an antibody epitope from the amyloidogenic prion protein. Dynamic covalent chemistry is the basis for the spontaneous condensation of 2, 3, 4 or 6 peptides with qualified polyol templates presenting the required number of bioorthogonal ligation sites. To study this process in aqueous solution, the N-terminal amino acid of a 13-mer peptide is first acylated with 4-carboxy-benzoboroxole (1-hydroxy-1,3-dihydrobenzo[c][1,2] oxaborole-5-carboxylic acid) and then mixed with the template to obtain self-assembled miniamyloids of specified degree of oligomerization...
April 27, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28421689/on-resin-n-formylation-of-peptides-a-head-to-head-comparison-of-reagents-in-solid-phase-synthesis-of-ligands-for-formyl-peptide-receptors
#19
COMPARATIVE STUDY
Simon Bendt Christensen, Anna Mette Hansen, Henrik Franzyk
4-Nitrophenyl formate was found to be the most convenient reagent in solid-phase formylation of peptides with a high formylation degree within 20 min to 3 h depending on reaction temperature and length of peptide.
May 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28326661/role-of-single-disulfide-linkages-in-the-folding-and-activity-of-scyllatoxin-based-bh3-domain-mimetics
#20
Danushka Arachchige, M Margaret Harris, Zachary Coon, Jacob Carlsen, Justin M Holub
Anti-apoptotic Bcl-2 proteins are implicated in pathogenic cell survival and have attracted considerable interest as therapeutic targets. We recently developed a class of synthetic peptide based on scyllatoxin (ScTx) designed to mimic the helical BH3 interaction domain of the pro-apoptotic Bcl-2 protein Bax. In this communication, the contribution of single disulfides in the folding and function of ScTx-Bax peptides was investigated. We synthesized five ScTx-Bax variants, each presenting a different combination of native disulfide linkage and evaluated their ability to directly bind Bcl-2 in vitro...
May 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
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