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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/30221432/ascidiacyclamides-containing-oxazoline-and-thiazole-motifs-assume-square-conformations-and-show-high-cytotoxicity
#1
Akiko Asano, Takeshi Yamada, Taizo Taniguchi, Masahiro Sasaki, Kenji Yoza, Mitsunobu Doi
Four cyclic octapeptides were designed from ascidiacyclamide [cyclo(-Ile-Oxz-D-Val- Thz-)2 ] (ASC, 1) to investigate the effects of oxazoline (Oxz) and thiazole (Thz) rings on the structures and cytotoxicities of the peptides. cyclo(-Ile-Thz-D-Val-Oxz-)2 (2) had the same number of Oxz and Thz rings as ASC, but the ring positions were switched. cyclo(-Ile-Oxz-D-Val-Thz-Ile-Thz-D-Val-Thz-) (3) and cyclo(-Ile-Thz-D-Val-Oxz-Ile-Thz-D-Val-Thz-) (4) contained one Oxz and three Thz rings within the molecule. All Oxz rings were substituted with Thz in cyclo(-Ile-Thz-D-Val-Thz-)2 (5)...
September 17, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/30168238/a-stable-meta-carborane-enables-the-generation-of-boron-rich-peptide-agonists-targeting-the-ghrelin-receptor
#2
Dennis J Worm, Sylvia Els-Heindl, Martin Kellert, Robert Kuhnert, Stefan Saretz, Johannes Koebberling, Bernd Riedl, Evamarie Hey-Hawkins, Annette G Beck-Sickinger
Boron neutron capture therapy (BNCT) is a binary cancer therapy, which combines the biochemical targeting of a boron-containing drug with the regional localization of radiation treatment. Although the concept of BNCT has been known for decades, the selective delivery of boron into tumor cells remains challenging. G protein-coupled receptors that are overexpressed on cancer cells in combination with peptidic ligands can be potentially used as shuttle system for a tumor-directed boron uptake. In this study, we present the generation of short, boron-rich peptide conjugates that target the ghrelin receptor...
August 31, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/30112781/an-amphipathic-cyclic-tetrapeptide-scaffold-containing-halogenated-%C3%AE-2-2-amino-acids-with-activity-against-multiresistant-bacteria
#3
Marianne H Paulsen, Eskil André Karlsen, Dominik Ausbacher, Trude Anderssen, Annette Bayer, Philipp Ochtrop, Christian Hedberg, Tor Haug, Johanna U Ericson Sollid, Morten B Strøm
The present study describes the synthesis and biological studies of a small series of head-to-tail cyclic tetrapeptides of the general structure c(Lys-β2,2 -Xaa-Lys) containing one lipophilic β2,2 -amino acid and Lys, Gly, Ala, or Phe as the Xaa residue in the sequence. The peptides were investigated for antimicrobial activity against gram-positive and gram-negative reference strains and 30 multiresistant clinical isolates including strains with extended spectrum β-lactamase-carbapenemase (ESBL-CARBA) production...
August 15, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/30084214/the-effect-of-conjugation-on-antitumor-activity-of-vindoline-derivatives-with-octaarginine-a-cell-penetrating-peptide
#4
Zoltán Bánóczi, András Keglevich, Ildikó Szabó, Ivan Ranđelović, Zita Hegedüs, Fruzsina L Regenbach, Péter Keglevich, Zsófia Lengyel, Álmos Gorka-Kereskényi, Zsófia Dubrovay, Viktor Háda, Áron Szigetvári, Csaba Szántay, László Hazai, József Tóvári, Ferenc Hudecz
Some Vinca alkaloids (eg, vinblastine, vincristine) have been widely used as antitumor drugs for a long time. Unfortunately, vindoline, a main alkaloid component of Catharanthus roseus (L.) G. Don, itself, has no antitumor activity. In our novel research program, we have prepared and identified new vindoline derivatives with moderate cytostatic activity. Here, we describe the effect of conjugation of vindoline derivative with oligoarginine (tetra-, hexa-, or octapeptides) cell-penetrating peptides on the cytostatic activity in vitro and in vivo...
August 6, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/30232828/35-th-european-peptide-symposium-26-th-31-st-august-2018-dublin-city-university-ireland
#5
(no author information available yet)
No abstract text is available yet for this article.
September 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/30062707/osmolytes-modulate-polyglutamine-aggregation-in-a-sequence-dependent-manner
#6
Itika Saha, Virender Singh, Gunasekhar Burra, Ashwani Kumar Thakur
Osmolytes stabilize protein structure and suppress protein aggregation. The mechanism of how osmolytes impact polyglutamine (polyQ) aggregation implicated in Huntington's disease was studied. By using a reverse-phase chromatography assay, we show that methylamines-trimethylamine N-oxide and betaine are generic in enhancing polyQ aggregation, while a disaccharide trehalose and an amino acid citrulline moderately retard polyQ aggregation in a sequence specific manner. Despite the altered kinetics, the fundamental nucleation mechanism of polyQ aggregation and the nature of end stage aggregates remains unaffected...
August 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/30019359/on-the-design-and-efficacy-assessment-of-self-assembling-peptide-based-hydrogel-glycosaminoglycan-mixtures-for-potential-repair-of-early-stage-cartilage-degeneration
#7
A Barco, E Ingham, J Fisher, H Fermor, R P W Davies
Peptide-based hydrogels are of interest for their potential use in regenerative medicine. Combining these hydrogels with materials that may enhance their physical and biological properties, such as glycosaminoglycans, has the potential to extend their range of biomedical applications, for example in the repair of early cartilage degeneration. The aim of this study was to combine three self-assembling peptides (P11 -4, P11 -8, and P11 -12) with chondroitin sulphate at two molar ratios of 1:16 and 1:64 in 130 and 230 mM Na+ salt concentrations...
August 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/30009478/further-applications-of-classical-amide-coupling-reagents-microwave-assisted-esterification-on-solid-phase
#8
Risa Takayama, Shun Hayakawa, Hiroshi Hinou, Fernando Albericio, Fayna Garcia-Martin
Ester linkage (s) is a key chemical connector in organic chemistry, including natural products, peptides, and synthetic polymers. We herein describe a straightforward method for the efficient formation of ester linkage (s) on solid-phase. This method simply involves the use of amide coupling reagents under microwave irradiation. The robustness of this method relies on the use of classical solid-phase coupling reagents, heating by microwave irradiation, and a short time period, which results in high yields and the minimization of racemization...
August 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/30009430/racemic-crystal-structures-of-peptide-toxins-gsmtx4-prepared-by-protein-total-synthesis
#9
Qian Qu, Shuai Gao, Yi-Ming Li
The Piezo channel is a versatile mechanosensitive cation channel that mediates tactile, vascular development, and proprioception. GsMTx4 is the only reported inhibitor specifically targeting Piezo channels. Although the sequence of GsMTx4 is reported, the crystal structure of GsMTx4 is still unknown. Here, we achieved the two-segment synthesis of GsMTx4 and its enantiomer, enGsMTx4, through hydrazide based Native Chemical Ligation, and analyzed the crystal structure of GsMTx4 through the racemic crystallization technology...
August 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/30009393/quantification-of-hydrolyzed-peptides-and-proteins-by-amino-acid-fluorescence
#10
Martina D Allenspach, Jens A Fuchs, Nicolas Doriot, Jan A Hiss, Gisbert Schneider, Christian Steuer
Reliable quantification of peptides and proteins is essential for drug discovery. We report the successful development and validation of an accurate and broadly applicable high performance liquid chromatography hyphenated to fluorescence detector procedure for the quantitative determination of the aromatic amino acids tyrosine, phenylalanine, and tryptophan, without relying on derivatization chemistry. Using ion-pair chromatography, fluorescent amino acids were clearly separated within 10 minutes. The hydrolysis of peptides was performed under acidic and heated conditions to yield the monomeric building blocks...
August 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29971858/imidazole-dipeptides-can-quench-toxic-4-oxo-2-e-nonenal-molecular-mechanism-and-mass-spectrometric-characterization-of-the-reaction-products
#11
Fumiya Tatsuno, Seon Hwa Lee, Tomoyuki Oe
Imidazole dipeptides, such as carnosine (β-alanyl-l-histidine) and anserine (β-alanyl-Nπ -methyl-l-histidine), are highly localized in excitable tissues, including skeletal muscle and nervous tissue, and play important roles such as scavenging reactive oxygen species and quenching reactive aldehydes. We have demonstrated several reactions between imidazole dipeptides (namely, carnosine, and anserine) and a lipid peroxide-derived reactive aldehyde 4-oxo-2(E)-nonenal. Seven carnosine adducts and two anserine adducts were characterized using liquid chromatography/electrospray ionization-multiple-stage mass spectrometry...
August 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29943487/influence-of-reaction-conditions-on-the-oxidation-of-thiol-groups-in-model-peptidomimetic-oligoureas
#12
Karolina Pulka-Ziach
Working with thiols is associated with the risk of unwanted oxidation reactions, which includes the formation of disulfides. Here, the use of short peptidomimetic oligoureas as a model system to study the influence of reaction conditions on the thiol oxidation process is described. The formation of disulfide bond is usually performed in aqueous solutions; in this study, it was shown that the oxidation reaction occurs also in organic medium. It was discovered that the rate of the oxidation reaction strongly depends on the type of solvent, which is the consequence of the change of the oxidant (air or DMSO), the temperature, and the presence (or absence) of base...
August 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29920844/synthesis-and-purification-of-self-assembling-peptide-oligonucleotide-conjugates-by-solid-phase-peptide-fragment-condensation
#13
Mahnseok Kye, Yong-Beom Lim
Peptide-oligonucleotide conjugates (POCs) are interesting molecules as they covalently combine 2 of the most important biomacromolecules. Sometimes, the synthesis of POCs involves unexpected difficulties; however, POCs with self-assembling propensity are even harder to synthesize and purify. Here, we show that solid-phase peptide fragment condensation combined with thiol-maleimide or copper-catalyzed azide-alkyne cycloaddition click chemistries is useful for the syntheses of self-assembling POCs. We describe guidelines for the selection of reactive functional groups and their placement during the conjugation reaction and consider the cost-effectiveness of the reaction...
August 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29900628/acyclic-peptides-incorporating-the-d-phe-2-abz-turn-motif-investigations-on-antimicrobial-activity-and-propensity-to-adopt-%C3%AE-hairpin-conformations
#14
Alan J Cameron, Kyriakos G Varnava, Patrick J B Edwards, Elena Harjes, Vijayalekshmi Sarojini
Three linear peptides incorporating d-Phe-2-Abz as the turn motif are reported. Peptide 1, a hydrophobic β-hairpin, served as a proof of principle for the design strategy with both NMR and CD spectra strongly suggesting a β-hairpin conformation. Peptides 2 and 3, designed as amphipathic antimicrobials, exhibited broad spectrum antimicrobial activity, with potency in the nanomolar range against Staphylococcus aureus. Both compounds possess a high degree of selectivity, proving non-haemolytic at concentrations 500 to 800 times higher than their respective minimal inhibitory concentrations (MICs) against S...
August 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29862598/a-general-method-for-preparation-of-n-boc-protected-or-n-fmoc-protected-%C3%AE-%C3%AE-didehydropeptide-building-blocks-and-their-use-in-the-solid-phase-peptide-synthesis
#15
Grzegorz Wołczański, Marek Lisowski
N-(tert-butyloxycarbonyl) or N-(9-fluorenylmethoxycarbonyl) dipeptides with C-terminal (Z)-α,β-didehydrophenylalanine (∆Z Phe), (Z)-α,β-didehydrotyrosine (∆Z Tyr), (Z)-α,β-didehydrotryptophan (∆Z Trp), (Z)-α,β-didehydromethionine (∆Z Met), (Z)-α,β-didehydroleucine (∆Z Leu), and (Z/E)-α,β-didehydroisoleucine (∆Z/E Ile) were synthesised from their saturated analogues via oxidation of intermediate 2,5-disubstituted-oxazol-5-(4H)-ones (also known as azlactones) with pyridinium tribromide followed by opening of the produced unsaturated oxazol-5-(4H)-one derivatives in organic-aqueous solution with a catalytic amount of trifluoroacetic acid or by a basic hydrolysis...
August 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/30133959/7-th-international-meeting-on-antimicrobial-peptides
#16
EDITORIAL
Håvard Jenssen
No abstract text is available yet for this article.
July 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29962075/fluorinated-antimicrobial-lysine-based-peptidomimetics-with-activity-against-methicillin-resistant-staphylococcus-pseudintermedius
#17
Natalia Molchanova, Paul R Hansen, Peter Damborg, Henrik Franzyk
Staphylococcus pseudintermedius is the predominant opportunistic pathogen in dogs causing primarily integumentary infections such as pyoderma and otitis. The worldwide emergence of methicillin-resistant S. pseudintermedius (MRSP) constitutes a significant health problem for companion animals in veterinary medicine. Thus, discovery of novel agents for treatment of MRSP-associated infections is highly warranted. In the present work, structure-activity relationships (based on testing of 37 peptidomimetics) have been explored with the aim of determining the influence of oligomer length as well as effect of fluorination, end-group modification, and length of hydrophobic side chains...
July 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29938867/neurotensin-substance-p-and-insulin-enhance-cell-migration
#18
Michelle V Mouritzen, Sali Abourayale, Rooshanie Ejaz, Christine B Ardon, Eugenia Carvalho, Louise T Dalgaard, Martin Roursgaard, Håvard Jenssen
Neurotensin, substance P, and insulin have been demonstrated to improve wound healing in vivo. However, the mechanism behind their effect is still not fully understood. This study investigates the effects leading to enhanced scratch closure by these peptides in vitro. The skin keratinocyte cell line, HaCaT, was used to test scratch closure effects of the peptides and alterations of cytokine levels. HUVEC cells were used to test the angiogenic effect of the peptides. Furthermore, clinical isolates of Staphylococcus lugdunensis were used to examine the potential antimicrobial activity of each peptide...
July 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29900637/human-apolipoprotein-e-as-a-reservoir-of-cryptic-bioactive-peptides-the-case-of-apoe-133-167
#19
Anna Zanfardino, Andrea Bosso, Giovanni Gallo, Valeria Pistorio, Michela Di Napoli, Rosa Gaglione, Eliana Dell'Olmo, Mario Varcamonti, Eugenio Notomista, Angela Arciello, Elio Pizzo
Bioactive peptides derived from the receptor-binding region of human apolipoprotein E have previously been reported. All these peptides, encompassing fragments of this region or designed on the basis of short repeated cationic sequences identified in the same region, show toxic activities against a broad spectrum of bacteria and interesting immunomodulatory effects. However, the ability of these molecules to exert antibiofilm properties has not been described so far. In the present work, we report the characterization of a novel peptide, corresponding to residues 133 to 167 of human apolipoprotein E, here named ApoE (133-167)...
July 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29873139/random-mixtures-of-antimicrobial-peptides-inhibit-bacteria-associated-with-pasteurized-bovine-milk
#20
Tal Stern Bauer, Zvi Hayouka
The shelf life of pasteurized bovine milk is limited by microorganism activity as surviving bacteria continue to grow in the bovine milk, eventually causing milk spoilage. In the current study, we used matrix-assisted laser desorption ionization time of flight mass spectrometry to identify pasteurized bovine milk-associated mesophilic and psychrotrophic bacteria. We have recently designed random cationic peptide mixtures that possess strong antimicrobial and antibiofilm properties. These compounds are cheap and easy to synthesize and represent a new class of antimicrobial agents...
July 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
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