Antitumor activity of opiorphin, sialorphin and their conjugates with a peptide klaklakklaklak
This is the study on the effect of opiorphin, sialorphin and their analogs on antitumor activity. We demonstrated that conjugation of opiorphin and sialorphin with a proapoptotic, antimicrobial peptide klak (klaklakklaklak) led to compounds (opio‐klak and sialo‐klak) that were cytotoxic against cancer cells (LN18, PC3, A549, HCT116 and B10‐F16) in the MTT test. The conjugated analogs were designed to increase the effectiveness of the peptide. The opio‐klak derivative was the most effective in the in vitro assays and led to a decrease in viability of cancer cells over time as compared with that of untreated controls...
Source: Journal of Peptide Science - September 30, 2016 Category: Biochemistry Authors: El żbieta Kamysz, Ryszard Smolarczyk, Tomasz Cichoń, Magdalena Jarosz‐Biej, Emilia Sikorska, Małgorzata Sobocińska, Maciej Jaśkiewicz, Wojciech Kamysz Tags: Research Article Source Type: research
Development of lipopolysaccharide ‐mimicking peptides and their immunoprotectivity against Vibrio cholerae serogroup O1
In conclusion, these peptides are mimicking LPS and can potentially act as vaccine candidates against V. cholerae. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.
Phage particles displaying 12 amino acid peptides were selected from phage library using camelid VHH against Vibrio cholerae LPS in a three rounds of panning. Because these peptides are mimicking, the antigenic epitopes of LPS, therefore, are used as vaccine candidate to immunized mice. These peptides induced the immune system against V. cholerae and inhibit its attachment and colonization. (Source: Journal of Peptide Science)
Source: Journal of Peptide Science - September 30, 2016 Category: Biochemistry Authors: Fatemeh Mohammad Pour Ghazi, Seyed Latif Mousavi Gargari Tags: Research Article Source Type: research
Suppressing the epimerization of endothioamide peptides during Fmoc/t ‐Bu‐based solid phase peptide synthesis
Despite a number of intriguing utilities associated with thioamide‐containing peptides and proteins in the context of biophysics, pharmacology and chemical biology, it has hitherto remained as one of the underexplored territories of peptidomimetics. The synthesis of long mono to multiply substituted endothioamide peptides is invariably accompanied with severe epimerization, oxoamide formation and various other undesired side reactions, resulting in messy product profiles. This has completely restrained their use as novel chemical tools for biological studies. During the chain elongation of an N‐terminally located thioa...
Source: Journal of Peptide Science - September 30, 2016 Category: Biochemistry Authors: Somnath Mukherjee, Jayanta Chatterjee Tags: Rapid Communication Source Type: research
Collagen and keratin polypeptide models for assessing the natural and artificial protein decay of organic materials
Among the materials constituting the natural and cultural heritage, organic materials of proteinaceous origin as bone (collagen), parchment and woolen textiles (keratin) are the most susceptible to damage and decay because of their exposure to air pollution, inappropriate values of ambient temperature, humidity and light. Aiming at contributing to the development of a reliable and reproducible immunoassay for the evaluation of collagen and keratin decay, three polypeptide models of these proteins were designed, synthesized and studied. Polypeptide [Pro‐Ser(OBzl)‐Gly]n incorporates the typical motif Pro‐X‐Gly of col...
Source: Journal of Peptide Science - September 30, 2016 Category: Biochemistry Authors: Evmorfia Fotou, Maria Sakarellos ‐Daitsiotis, Eleni Ioakeimoglou, Eleni Tziamourani, Ekaterini Malea, George Panayiaris, Eugenia Panou‐Pomonis Tags: Research Article Source Type: research
Immune activation with peptide assemblies carrying Lewis y tumor ‐associated carbohydrate antigen
Molecular assemblies varying morphologies in a wide range from spherical micelle, nanosheet, curved sheet, nanotube and vesicle were prepared and loaded with Lewis y (Ley) tumor‐associated carbohydrate antigen on the assembly surface. The molecular assemblies were composed of poly(sarcosine)m‐block‐poly(L‐lactic acid)30 (m = 15 or 50, Lactosome), poly(sarcosine)m‐block‐(D/L‐Leu‐Aib)n (m = 22 or 30, n = 6 or 8) and their combinations. The molecular assemblies carrying Ley on the surface were administered in BALB/c nu/nu mice. The major epitopes of the molecular assemblies are commonly Ley and pol...
Source: Journal of Peptide Science - September 30, 2016 Category: Biochemistry Authors: Yuji Yamazaki, Naoki Watabe, Hiroaki Obata, Eri Hara, Masashi Ohmae, Shunsaku Kimura Tags: Special Issue Article Source Type: research
Design of peptidase ‐resistant peptide inhibitors of myosin light chain kinase
Myosin light chain kinase (MLCK) is a key regulator of various forms of cell motility including smooth muscle contraction, cell migration, cytokinesis, receptor capping, secretion, etc. Inhibition of MLCK activity in endothelial and epithelial monolayers using cell‐permeant peptide Arg‐Lys‐Lys‐Tyr‐Lys‐Tyr‐Arg‐Arg‐Lys (PIK, Peptide Inhibitor of Kinase) allows protecting the barrier capacity, suggesting a potential medical use of PIK. However, low stability of L‐PIK in a biological milieu prompts for development of more stable L‐PIK analogues for use as experimental tools in basic and drug‐oriented bi...
Source: Journal of Peptide Science - August 31, 2016 Category: Biochemistry Authors: Asker Y. Khapchaev, Olga A. Kazakova, Mikhail V. Samsonov, Maria V. Sidorova, Valery N. Bushuev, Elena L. Vilitkevich, Andrey A. Az'muko, Alexander S. Molokoedov, Zhanna D. Bespalova, Vladimir P. Shirinsky Tags: Research Article Source Type: research
Comparative studies of adhesion peptides based on l ‐ or d‐amino acids
Detailed studies comparing solid‐supported l‐ or d‐amino acid adhesion peptides based on the sequence KLHRIRA were performed. Stability towards proteases and levels of cellular adhesion to the otherwise inert surface of PEGA resin were compared by using fluorescently labelled peptides. A clear difference in the peptide stability towards cleavage by subtilisin, trypsin, or papain was observed. However, all of the on‐bead peptides provided an optimal surface for cell adhesion and proliferation. In long‐term experiments, these properties were still found to be similar on the resins modified either with l‐ or with ...
Source: Journal of Peptide Science - August 31, 2016 Category: Biochemistry Authors: Sergey Nikitin, Daniel Palmer, Morten Meldal, Frederik Diness Tags: Research Article Source Type: research
Synthesis and characterization of β‐peptide helices as transmembrane domains in lipid model membranes
Aggregation, orientation and dynamics of transmembrane helices are of relevance for protein function and transmembrane signaling. To explore the interactions of transmembrane helices and the interdependence of peptide structure and lipid composition of the membranes, β‐peptides were explored as model transmembrane domains. Various hydrophobic β‐peptide sequences were synthesized by solid phase peptide synthesis. Conformational analyses of β‐peptide helices were performed in organic solvents (methanol and 2,2,2‐trifluoroethanol) and in large unilamellar liposomes (dimyristoylphosphatidylcholine, dipalmitoylphosph...
Source: Journal of Peptide Science - August 31, 2016 Category: Biochemistry Authors: Denis M. Pahlke, Ulf Diederichsen Tags: Research Article Source Type: research
Total synthesis, structural, and biological evaluation of stylissatin A and related analogs
We report here the solid‐phase synthesis, structural studies, and biological evaluation of cyclic peptides stylissatin A, proline rotamer of stylissatin A, (D‐allo‐Ile2)‐stylissatin A, and six analogues of stylissatin A. The position of macrocyclization was found to influence the proline rotamer population of synthetic sytlissatin A. The synthetic stylissatin A, its epimer and trans, trans rotamer potently inhibited the NO. production. Related analogues of stylissatin A were identified as more potent inhibitors of interleukin 2 release. (Source: Journal of Peptide Science)
Source: Journal of Peptide Science - August 15, 2016 Category: Biochemistry Authors: Farzana Shaheen, Almas Jabeen, Samreen Ashraf, Muhammad Nadeem ‐ul‐Haque, Zafar Ali Shah, Muhammad Asad Ziaee, Nida Dastagir, A. Ganesan Tags: Research Article Source Type: research
Issue Information
(Source: Journal of Peptide Science)
Source: Journal of Peptide Science - August 15, 2016 Category: Biochemistry Tags: Issue Information Source Type: research
Novel pentapeptide, PALAL, derived from a bony fish elicits contraction of the muscle in starfish Patiria pectinifera
A bioactive peptide mimicking peptide‐signaling molecules has been isolated from the skin extract of fish Channa argus which caused contraction of the apical muscle of a starfish Patiria pectinifera, a deuterostomian invertebrate. The primary structure of the isolated pentapeptide comprises amino acid sequence of H‐Pro‐Ala‐Leu‐Ala‐Leu‐OH (PALAL) with a molecular mass of 483.7 Da. Pharmacological activity of PALAL, dosage ranging from 10−9 to 10−5 M, revealed concentration‐dependent contraction of the apical muscles of P. pectinifera and Asterias amurensis. However, PALAL was not active on the intestin...
Source: Journal of Peptide Science - July 31, 2016 Category: Biochemistry Authors: Hye ‐Jin Go, Chan‐Hee Kim, Hye Young Oh, Nam Gyu Park Tags: Research Article Source Type: research
Microwave ‐assisted cleavage of Alloc and Allyl Ester protecting groups in solid phase peptide synthesis
Orthogonal protection of amino acid side chains in solid phase peptide synthesis allows for selective deprotection of side chains and the formation of cyclic peptides on resin. Cyclizations are useful as they may improve the activity of the peptide or improve the metabolic stability of peptides in vivo. One cyclization method often used is the formation of a lactam bridge between an amine and a carboxylic acid. It is desirable to perform the cyclization on resin as opposed to in solution to avoid unwanted side reactions; therefore, a common strategy is to use –Alloc and –OAllyl protecting groups as they are compatible ...
Source: Journal of Peptide Science - July 31, 2016 Category: Biochemistry Authors: Krista R. Wilson, Seth Sedberry, Robyn Pescatore, Daniel Vinton, Brian Love, Sarah Ballard, Bradley C. Wham, Stacy K. Hutchison, Eric J. Williamson Tags: Rapid Communication Source Type: research
Removal of the 5 ‐nitro‐2‐pyridine‐sulfenyl protecting group from selenocysteine and cysteine by ascorbolysis
We previously reported on a method for the facile removal of 4‐methoxybenzyl and acetamidomethyl protecting groups from cysteine (Cys) and selenocysteine (Sec) using 2,2′‐dithiobis‐5‐nitropyridine dissolved in trifluoroacetic acid, with or without thioanisole. The use of this reaction mixture removes the protecting group and replaces it with a 2‐thio(5‐nitropyridyl) (5‐Npys) group. This results in either a mixed selenosulfide bond or disulfide bond (depending on the use of Sec or Cys), which can subsequently be reduced by thiolysis. A major disadvantage of thiolysis is that excess thiol must be used to driv...
Source: Journal of Peptide Science - July 31, 2016 Category: Biochemistry Authors: Emma J. Ste. Marie, Erik L. Ruggles, Robert J. Hondal Tags: Rapid Communication Source Type: research
Synthesis and biological activity of FGLamide allatostatin analogs with Phe3 residue modifications
This study will be useful for the design of new allatostatin analogs for insect management. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.
A series of Phe3 residue‐modified analogs were designed and synthesized. Bioassay results indicated that analogs 4, 11 and 13 showed stronger ability than lead H17 to inhibit JH production by corpora allata of Diploptera punctata. Removing the methylene group of Phe3, or an o‐ or p‐ halogen‐substituted benzene ring could increase the activity of the analogs containing six‐membered aromatic rings. (Source: Journal of Peptide Science)
Source: Journal of Peptide Science - July 31, 2016 Category: Biochemistry Authors: Yong Xie, Meizi Wang, Li Zhang, Xiaoqing Wu, Xinling Yang, Stephen S. Tobe Tags: Research Article Source Type: research
Biosynthetic engineering of nonribosomal peptide synthetases
From the evolutionary melting pot of natural product synthetase genes, microorganisms elicit antibiotics, communication tools, and iron scavengers. Chemical biologists manipulate these genes to recreate similarly diverse and potent biological activities not on evolutionary time scales but within months. Enzyme engineering has progressed considerably in recent years and offers new screening, modelling, and design tools for natural product designers. Here, recent advances in enzyme engineering and their application to nonribosomal peptide synthetases are reviewed. Among the nonribosomal peptides that have been subjected to b...
Source: Journal of Peptide Science - July 28, 2016 Category: Biochemistry Authors: Hajo Kries Tags: Review Source Type: research
