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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/29971858/imidazole-dipeptides-can-quench-toxic-4-oxo-2-e-nonenal-molecular-mechanism-and-mass-spectrometric-characterization-of-the-reaction-products
#1
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...
July 3, 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
#2
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 2, 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
#3
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...
June 25, 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
#4
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...
June 25, 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
#5
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...
June 19, 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
#6
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)...
June 14, 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
#7
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...
June 14, 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
#8
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...
June 6, 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
#9
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...
June 3, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29845683/development-and-evaluation-of-cationic-amphiphilic-antimicrobial-2-5-diketopiperazines
#10
Christophe Labrière, Nahid Kondori, Josefin Seth Caous, Marc Boomgaren, Kerstin Sandholm, Kristina N Ekdahl, Jørn H Hansen, Johan Svenson
No abstract text is available yet for this article.
May 29, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29808604/induced-expression-of-cathelicidins-in-trout-oncorhynchus-mykiss-challenged-with-four-different-bacterial-pathogens
#11
Michela Furlan, Umberto Rosani, Stefano Gambato, Paola Irato, Amedeo Manfrin, Mario Mardirossian, Paola Venier, Alberto Pallavicini, Marco Scocchi
Cathelicidins are an important family of antimicrobial peptide effectors of innate immunity in vertebrates. Two members of this group, CATH-1 and CATH-2, have been identified and characterized in teleosts (ray-finned fish). In this study, we investigated the expression of these genes in different tissues of rainbow trout challenged with 4 different inactivated pathogens. By using qPCR, we detected a strong induction of both cath-1 and cath-2 genes within 24 hours after intraperitoneal inoculation with Lactococcus garvieae, Yersinia ruckeri, Aeromonas salmonicida, or Flavobacterium psychrophilum cells...
May 28, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29799150/action-of-antimicrobial-peptides-and-their-prodrugs-on-model-and-biological-membranes
#12
Éanna Forde, Ghady Shafiy, Deirdre Fitzgerald-Hughes, Adam A Strömstedt, Marc Devocelle
Antimicrobial peptides (AMPs) are promising broad-spectrum antibiotic candidates in the wake of multi-drug resistant pathogens. Their clinical use still requires a solution based on lead optimisation and/or formulation to overcome certain limitations, such as unwanted cytotoxicity. A prodrug approach could overcome this safety barrier and can be achieved through reversible reduction or neutralisation of the AMPs' net cationic charge. By prodrug activation through pathogen associated enzymes, this approach could increase the therapeutic index of membrane active peptides...
May 24, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29737589/ll-37-fragments-have-antimicrobial-activity-against-staphylococcus-epidermidis-biofilms-and-wound-healing-potential-in-hacat-cell-line
#13
Paola Saporito, Michelle Vang Mouritzen, Anders Løbner-Olesen, Håvard Jenssen
Staphylococcus epidermidis is a common nosocomial pathogen able to form biofilms in indwelling devices, resulting in chronic infections, which are refractory to antibiotics treatment. Staphylococcal biofilms are also associated with the delayed reepithelization and healing of chronic wounds. The human cathelicidin peptide LL-37 has been proven active against S. epidermidis biofilms in vitro and to promote wound healing. As previous studies have demonstrated that fragments of LL-37 could possess an equal antibacterial activity as the parent peptide, we tested whether shorter (12-mer) synthetic fragments of LL-37 maintained the antibiofilm and/or immune modulating activity, aiming at the identification of essential regions within the LL-37 parent sequence...
May 8, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29870123/influences-of-disulfide-connectivity-on-structure-and-antimicrobial-activity-of-tachyplesin-i
#14
Juan Shi, Lok-Yan So, Fangling Chen, Jiazhen Liang, Ho-Yin Chow, Kwok-Yin Wong, Shengbiao Wan, Tao Jiang, Rilei Yu
Tachyplesin I is a potent antimicrobial peptide with broad spectrum of antimicrobial activity. It has 2 disulfide bonds and can form 3 disulfide bond isomers. In this study, the structure and antimicrobial activity of 3 tachyplesin I isomers (tachyplesin I, 3C12C, 3C7C) were investigated using molecular dynamic simulations, circular dichroism structural study, as well as antimicrobial activity and hemolysis assay. Our results suggest that in comparison to the native peptide, the 2 isomers (3C12C, 3C7C) have substantial structural and activity variations...
June 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29870122/novel-tool-in-rheumatoid-arthritis-diagnosis-the-usage-of-urease-flap-region-peptidomimetics
#15
Iwona Konieczna, Inga Relich, Maciej Durajski, Lukasz Lechowicz, Magdalena Chrapek, Jozef Gaweda, Justyna Fraczyk, Zbigniew J Kaminski
Rheumatoid arthritis (RA) is an autoimmune inflammatory disease. Early diagnosis can prevent joint erosion. However, available biomarkers do not always allow for clear distinction between RA and non-RA individuals. It has become known that bacteria/viruses are among the environmental triggers that initiate RA via multiple molecular mechanisms. Thus, to better understand the role of bacteria in RA, we synthetized 6 peptidomimetics of bacterial ureases' flap region. These peptides were then used to distinguish RA patients from healthy people sera by immunoblotting...
June 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29737576/pvec-hydrophobic-n-terminus-is-critical-for-antibacterial-activity
#16
Begum Alaybeyoglu, Berna Sariyar Akbulut, Elif Ozkirimli
Cell-penetrating peptides (CPPs) are commonly defined by their shared ability to be internalized into eukaryotic cells, without inducing permanent membrane damage, and to improve cargo delivery. Many CPPs also possess antimicrobial action strong enough to selectively lyse microbes in infected mammalian cultures. pVEC, a CPP derived from cadherin, is able to translocate into mammalian cells, and it is also antimicrobial. Structure-activity relationship and sequence alignment studies have suggested that the hydrophobic N-terminus (LLIIL) of pVEC is essential for this peptide's uptake into eukaryotic cells...
June 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29700898/development-and-stability-of-a-heat-stable-formulation-of-carbetocin-for-the-prevention-of-postpartum-haemorrhage-for-use-in-low-and-middle-income-countries
#17
Mattias Malm, Ingbritt Madsen, Johan Kjellström
Postpartum haemorrhage is a leading cause of maternal death worldwide. Oxytocin, currently the drug of choice for prevention of PPH, requires constant refrigeration. In pursuit of an alternative medicine, Ferring Pharmaceuticals have developed a heat-stable formulation of carbetocin, an oxytocin analogue. This study aimed to define that formulation, and to investigate its stability under ICH climate zone IV conditions (30°C/75% relative humidity) for at least 3 years and at extreme temperatures, such as 60°C, for shorter periods of time...
June 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29676523/characterization-of-low-abundance-species-in-the-active-pharmaceutical-ingredient-of-cigb-300-a-clinical-grade-anticancer-synthetic-peptide
#18
Hilda Garay, Luis Ariel Espinosa, Yasser Perera, Aniel Sánchez, David Diago, Silvio E Perea, Vladimir Besada, Osvaldo Reyes, Luis Javier González
CIGB-300 is a first-in-class synthetic peptide-based drug of 25 amino acids currently undergoing clinical trials in cancer patients. It contains an amidated disulfide cyclic undecapeptide fused to the TAT cell-penetrating peptide through a beta-alanine spacer. CIGB-300 inhibits the CK2-mediated phosphorylation leading to apoptosis of tumor cells in vitro, and in vivo in cancer patients. Despite the clinical development of CIGB-300, the characterization of peptide-related impurities present in the active pharmaceutical ingredient has not been reported earlier...
June 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29656472/in-vitro-and-in-vivo-characterization-of-an-interleukin-15-antagonist-peptide-by-metabolic-stability-99m-tc-labeling-and-biological-activity-assays
#19
Yunier Rodríguez-Álvarez, Ania Cabrales-Rico, Alejandro Perera-Pintado, Anais Prats-Capote, Hilda E Garay-Pérez, Osvaldo Reyes-Acosta, Erik Pérez-García, Araceli Chico-Capote, Alicia Santos-Savio
Interleukin (IL)-15 is an inflammatory cytokine that constitutes a validated therapeutic target in some immunopathologies, including rheumatoid arthritis (RA). Previously, we identified an IL-15 antagonist peptide named [K6T]P8, with potential therapeutic application in RA. In the current work, the metabolic stability of this peptide in synovial fluids from RA patients was studied. Moreover, [K6T]P8 peptide was labeled with 99m Tc to investigate its stability in human plasma and its biodistribution pattern in healthy rats...
June 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29624787/insights-into-the-helix-sense-inversion-of-poly-%C3%AE-phenethyl-l-aspartate-by-two-dimensional-raman-correlation-spectroscopy
#20
Yuki Suzuki, Hidemine Furuya
In this study, the transition process of the helix-sense inversion of poly(β-phenethyl-L-aspartate) was investigated by Raman scattering and 2-dimensional correlation spectroscopy. Temperature-dependent Raman spectra were obtained during the helix-sense inversion. The results of 2-dimensional correlation analysis in the spectral regions of 1600-1800 and 3200-3400 cm-1 showed that the intensity changes of the side-chain ester C═O stretching bands occurred prior to those of amide A and amide I bands in the unwinding process of αR-helix on heating...
June 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
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