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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/29737589/ll-37-fragments-have-antimicrobial-activity-against-staphylococcus-epidermidis-biofilms-and-wound-healing-potential-in-hacat-cell-line
#1
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/29737576/pvec-hydrophobic-n-terminus-is-critical-for-antibacterial-activity
#2
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...
May 8, 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
#3
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...
April 27, 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
#4
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...
April 20, 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
#5
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...
April 15, 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
#6
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...
April 6, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29602217/a-fluorescently-labeled-undecapeptide-derived-from-a-protein-in-royal-jelly-of-the-honeybee-royalisin-for-specific-detection-of-oxidized-low-density-lipoprotein
#7
Akira Sato, Hiroto Unuma, Yoji Yamazaki, Keiichi Ebina
The probes for detection of oxidized low-density lipoprotein (ox-LDL) in plasma and in atherosclerotic plaques are expected to facilitate the diagnosis, prevention, and treatment of atherosclerosis. Recently, we have reported that a heptapeptide (Lys-Trp-Tyr-Lys-Asp-Gly-Asp, KP6) coupled through the ε-amino group of N-terminal Lys to fluorescein isothiocyanate (FITC), (FITC)KP6, can be useful as a fluorescent probe for specific detection of ox-LDL. In the present study, to develop a novel fluorescent peptide for specific detection of ox-LDL, we investigated the interaction (with ox-LDL) of an undecapeptide corresponding to positions 41 to 51 of a potent antimicrobial protein (royalisin, which consists of 51 residues; from royal jelly of honeybees), conjugated at the N-terminus to FITC in the presence of 6-amino-n-caproic acid (AC) linker, (FITC-AC)-royalisin P11, which contains both sequences, Phe-Lys-Asp and Asp-Lys-Tyr, similar to Tyr-Lys-Asp in (FITC)KP6...
March 30, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29582508/cell-assembled-nanoclusters-of-msc-targeting-gd-dota-peptide-as-a-t-2-contrast-agent-for-mri-cell-tracking
#8
Pengli Zhang, Yanhui Zhang, Binbin Li, Hailu Zhang, Haixia Lin, Zongwu Deng, Bo Tan
A cyclic peptide CC9 that targets cell membrane of mesenchymal stem cells (MSCs) is coupled with Gd-DOTA to yield a Gd-DOTA-CC9 complex as MRI contrast agent. It is used to label human MSCs (hMSCs) via electroporation. Electroporation-labeling of hMSCs with Gd-DOTA-CC9 induces cell-assembly of Gd-DOTA-CC9 nanoclusters in the cytoplasm, significantly promotes cell-labeling efficacy and intracellular retention time of the agent. In vitro MRI of labeled hMSCs exhibits significant signal reduction under T2 -weighted MRI, which can allow long-term tracking of labeled cell transplants in in vivo migration...
March 27, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29582506/exploring-hydrophobicity-limits-of-polyproline-helix-with-oligomeric-octahydroindole-2-carboxylic-acid
#9
Vladimir Kubyshkin, Nediljko Budisa
The polyproline-II helix is the most extended naturally occurring helical structure and is widely present in polar, exposed stretches and "unstructured" denatured regions of polypeptides. Can it be hydrophobic? In this study, we address this question using oligomeric peptides formed by a hydrophobic proline analogue, (2S,3aS,7aS)-octahydroindole-2-carboxylic acid (Oic). Previously, we found the molecular principles underlying the structural stability of the polyproline-II conformation in these oligomers, whereas the hydrophobicity of the peptide constructs remains to be examined...
March 27, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29582500/the-stereodynamics-of-macrocyclic-succinimide-thioethers
#10
Stefan Lenz, Philip Horx, Armin Geyer
Maleimide-thiol coupling is a popular bioconjugation strategy, but little is known about the stereoselectivity and the stereodynamics of the succinimide thioether formed in a biopolymer environment. We used thiol 1,4-addition for the macrocyclisation of 5 designed pentapeptides with the ringsize of hexapeptides because they incorporate the succinimide thioether (4-8). Both succinimide diastereomers are observed in the constrained macrocyclic rings in each case. In spite of the low diastereoselectivity of the macrocyclisation reaction, there is a significant influence of the amino acid environment on the epimerization rate of the succinimide...
March 27, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29575223/novel-side-reaction-accompanying-cyclization-of-glu-r1-glu-r2-dipeptides-via-lactamization-of-the-glu-r1-residue
#11
Vladislav Deigin, Olga Ksenofontova, Oleg Yatskin, Vadim Kublitsky, Vladimir Shmygarev, Rimma Abramovich, Maxim Dubinnyi, Vadim Ivanov
No abstract text is available yet for this article.
March 25, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29573035/synthesis-and-physicochemical-studies-of-amyloidogenic-hexapeptides-derived-from-human-cystatin-c
#12
Emilia Iłowska, Justyna Sawicka, Aneta Szymańska
Human cystatin C (hCC) is a low molecular mass protein that belongs to the cystatin superfamily. It is an inhibitor of extracellular cysteine proteinases, present in all human body fluids. At physiological conditions, hCC is a monomer, but it has a tendency to dimerization. Naturally occurring hCC mutant, with leucine in position 68 substituted by glutamine (L68Q), is directly involved in the formation of amyloid deposits, independently of other proteins. This process is the primary cause of hereditary cerebral amyloid angiopathy, observed mainly in the Icelandic population...
March 23, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29542264/molecular-design-of-antimicrobial-peptides-based-on-hemagglutinin-fusion-domain-to-combat-antibiotic-resistance-in-bacterial-infection
#13
Hui Ye
Antimicrobial peptides are derived from the viral fusion domain of influenza virus hemagglutinin based on rational analysis of the intermolecular interaction between peptides and bacterial outer membrane. It is revealed that the isolated viral fusion domain is a negatively charged peptide HAfp1-23 that cannot effectively interact with the anionic membrane. Conversion of the native HAfp1-23 to a positively charged peptide HAfp1-23 _KK by E11K/D19K mutation can promote the peptide-membrane interaction substantially; this confers to the peptide a moderate antibacterial potency against antibiotic-resistant bacterial strains...
March 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29542263/how-are-the-expression-patterns-of-gut-antimicrobial-peptides-modulated-by-human-gastrointestinal-diseases-a-bridge-between-infectious-inflammatory-and-malignant-diseases
#14
REVIEW
Paulo André Dias Bastos, Lúcio Lara Santos, Rui Miguel Pinheiro Vitorino
The human gut barrier is the tissue exposed to the highest load of microorganisms, harbouring 100 trillion bacteria. In addition, the gut's renewal rate outruns that of any other human tissue. Antimicrobial peptides (AMPs) are highly optimized defense molecules in the intestinal barrier optimized to maintain gastrointestinal homeostasis. Alterations in AMPs activity can lead to or result from human gastrointestinal diseases. In this review, unique, conserved, or otherwise regular alterations in the expression patterns of human AMPs across gastrointestinal inflammatory and infectious diseases were analyzed for pattern elucidation...
March 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29446187/4-fluorophenyl-3-nitro-2-pyridinesulfenate-as-a-practical-protecting-agent-for-amino-acids
#15
Yan Cui, Cédric Rentier, Akihiro Taguchi, Kentaro Takayama, Atsuhiko Taniguchi, Yoshio Hayashi
We report a new protecting agent (1, Npys-OPh(pF)) for 3-nitro-2-pyridine (Npy) sulfenylation of amino, hydroxy, and thiol functional groups. Several Npys phenoxides were synthesized from Npys chloride (Npys-Cl) and phenols in the presence of base in 1-step reaction, and their ability for Npy-sulfenylation was evaluated. As a result, 1 was selected as a new Npy-sulfenylation agent with advantages including improved physicochemical stability, more controllable reactivity, and easier handling than the conventional protecting agent Npys-Cl...
March 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29441631/respirable-powder-formulation-of-a-shortened-vasoactive-intestinal-peptide-analog-for-treatment-of-airway-inflammatory-diseases
#16
Hiroki Suzuki, Takahiro Mizumoto, Yoshiki Seto, Hideyuki Sato, Satomi Onoue
The aim of present study was to develop a respirable powder (RP) of a shortened vasoactive intestinal peptide (VIP) analog for inhalation. VIP and C-terminally truncated VIP analogs were synthesized with a solid-phase method. A structure-activity relationship (SAR) study was carried out in terms with binding and relaxant activities of the peptides. Prepared RP formulation of a shortened VIP analog was physicochemically characterized by morphological, in vitro aerodynamic, and pharmacological assessments. The SAR study demonstrated that the N-terminal 23 amino acid residues were required for biological activity of VIP...
March 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29430772/a-practical-diastereoselective-synthesis-of-bestatin
#17
Suisheng Shang, Andreas V Willems, Satendra S Chauhan
Diastereoselective addition of nitromethane to Boc-D-Phe-H in the presence of sodium hydride in diethyl ether/hexane containing 15-crown-5 and subsequent N,O-protection with 2,2-dimethoxypropane gave trans-oxazolidine in a diastereomeric ratio of >16:1. The oxazolidine was easily separated by column chromatography, which after Nef reaction was coupled to H-Leu-OtBu. The 8-step synthesis afforded (-)-bestatin in an overall yield of 24.7% after deprotection and ion exchange.
March 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29436155/design-of-cyclic-and-d-amino-acids-containing-peptidomimetics-for-inhibition-of-protein-protein-interactions-of-her2-her3
#18
Sandeep Pallerla, Himgauri Naik, Sitanshu Singh, Ted Gauthier, Rushikesh Sable, Seetharama D Jois
HER2 receptors are surface proteins belonging to the epidermal growth factor family of receptors. Their numbers are elevated in breast, lung, and ovarian cancers. HER2-positive cancers are aggressive, have higher mortality rate, and have a poor prognosis. We have designed peptidomimetics that bind to HER2 and block the HER2-mediated dimerization of epidermal growth factor family of receptors. Among these, a symmetrical cyclic peptidomimetic (compound 18) exhibited antiproliferative activity in HER2-overexpressing lung cancer cell lines with IC50 values in the nanomolar concentration range...
February 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29436154/new-methodology-for-automated-spot-synthesis-of-peptides-on-cellulose-using-1-3-5-triazine-derivatives-as-linkers-and-as-coupling-reagents
#19
Justyna Fraczyk, Małgorzata Walczak, Zbigniew J Kaminski
Two new rigid bi-aromatic linkers for synthesis of peptide arrays by SPOT methodology were obtained from cellulose treated with 2,4-dichloro-6-methoxy-1,3,5-triazine. Reaction with m-phenylenediamine gave non-cleavable TYPE I linker which enabled attachment of the peptides via resistant to harsh reaction conditions amide, ether, and amine bonds. Reaction with 3-Fmoc-aminobenzoic acid followed by thermal isomerization of the intermediate "superactive" ester producing an amide-like bond gave TYPE II linker that was very stable during peptide synthesis...
February 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29349894/assessment-of-the-potential-of-temporin-peptides-from-the-frog-rana-temporaria-ranidae-as-anti-diabetic-agents
#20
Vishal Musale, Bruno Casciaro, Maria Luisa Mangoni, Yasser H A Abdel-Wahab, Peter R Flatt, J Michael Conlon
Temporin A (FLPLIGRVLSGIL-NH2 ), temporin F (FLPLIGKVLSGIL-NH2 ), and temporin G (FFPVIGRILNGIL-NH2 ), first identified in skin secretions of the frog Rana temporaria, produced concentration-dependent stimulation of insulin release from BRIN-BD11 rat clonal β-cells at concentrations ≥1 nM, without cytotoxicity at concentrations up to 3 μM. Temporin A was the most effective. The mechanism of insulinotropic action did not involve an increase in intracellular Ca2+ concentrations. Temporins B, C, E, H, and K were either inactive or only weakly active...
February 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
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