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https://www.readbyqxmd.com/read/28429225/design-of-chemical-conjugate-for-targeted-therapy-of-multiple-sclerosis-based-of-constant-fragment-of-human-antibody-heavy-chain-and-peptoid-analog-of-autoantigen-mog35-55
#1
Y A Lomakin, A V Stepanov, D S Balabashin, N A Ponomarenko, I V Smirnov, A A Belogurov
Elimination of B cells producing autoantibodies to neuroantigens is considered as beneficial in the treatment of multiple sclerosis. Myelin oligodendrocyte glycoprotein (MOG) is a significant autoantigen in multiple sclerosis. It was shown that MOG-like peptoid AMogP3 can bind autoantibodies produced by pathological lymphocytes. We propose a structure of an innovative drug for targeted elimination of the pool of autoreactive B cells responsible for multiple sclerosis pathogenesis; this compound is a complex of peptoid AMogP3 with Fc fragment of human immunoglobulin...
April 21, 2017: Bulletin of Experimental Biology and Medicine
https://www.readbyqxmd.com/read/28401209/unusual-molecular-mechanism-behind-the-thermal-response-of-polypeptoids-in-aqueous-solutions
#2
Jianbo Ma, Sunting Xuan, Abby C Guerin, Tianyi Yu, Donghui Zhang, Daniel G Kuroda
Poly(α-peptoid)s, a structural isomer to polypeptides, have recently attracted a significant amount of scientific attention. However, the molecular mechanism behind the thermal response of this class of polymers is unknown. Here, the thermal response of two polypeptoids in aqueous solutions was studied by different methodologies, including dynamic light scattering, IR spectroscopies, NMR, etc. Our studies focused on two polypeptoids with identical alkyl side chain compositions, but different architecture; i...
April 12, 2017: Physical Chemistry Chemical Physics: PCCP
https://www.readbyqxmd.com/read/28322795/a-comprehensive-lipid-binding-and-activity-validation-of-a-cancer-specific-peptide-peptoid-hybrid-pps1
#3
Tanvi J Desai, D Gomika Udugamasooriya
We recently identified a peptide-peptoid hybrid, PPS1, which recognizes lipids that have an overall negative charge, such as phosphatidylserine (PS), phosphatidylglycerol (PG), phosphatidic acid (PA), and phosphatidylinositol (PI), but that does not bind to neutral lipids, such as phosphatidylcholine (PC), phosphatidylethanolamine (PE), and sphingomyelin (SM). The simple dimeric version of PPS1, PPS1D1, displayed strong cytotoxicity to cancer cells over normal cells in vitro and tumor burden in vivo. In this study, we comprehensively characterized the direct binding and activity of PPS1 on PS, PG, and PA using liposome-based assays and lung cancer cell lines that express these negatively charged lipids...
April 29, 2017: Biochemical and Biophysical Research Communications
https://www.readbyqxmd.com/read/28304024/methionine-and-seleno-methionine-type-peptide-and-peptoid-building-blocks-synthesized-by-five-component-five-center-reactions
#4
Goran N Kaluđerović, Muhammad Abbas, Hans Christian Kautz, Mohammad A M Wadaan, Claudia Lennicke, Barbara Seliger, Ludger A Wessjohann
A first example of 5-component 5-center reactions with isonitriles [Ugi-5CRs] is described. The extended Ugi type reactions involve selenoaldehydes as well as ammonia, both challenging reactants in multicomponent (MCR) systems, to generate methionine and Se-methionine moieties and derivatives as protected building blocks or for direct ligation in peptides or peptoids. The peptoid/peptide building blocks proved to be non-cytotoxic but increased the expression of genes encoding for stress protective selenoproteins (Gpx1)...
March 17, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28291947/evaluating-the-effect-of-peptoid-lipophilicity-on-antimicrobial-potency-cytotoxicity-and-combinatorial-library-design
#5
Jeremy A Turkett, Kevin L Bicker
Growing prevalence of antibiotic resistant bacterial infections necessitates novel antimicrobials, which could be rapidly identified from combinatorial libraries. We report the use of the peptoid library agar diffusion (PLAD) assay to screen peptoid libraries against the ESKAPE pathogens, including the optimization of assay conditions for each pathogen. Work presented here focuses on the tailoring of combinatorial peptoid library design through a detailed study of how peptoid lipophilicity relates to antibacterial potency and mammalian cell toxicity...
April 10, 2017: ACS Combinatorial Science
https://www.readbyqxmd.com/read/28272633/a-modular-platform-to-develop-peptoid-based-selective-fluorescent-metal-sensors
#6
Abigail S Knight, Rishikesh U Kulkarni, Effie Y Zhou, Jenna M Franke, Evan W Miller, Matthew B Francis
Despite the reduction in industrial use of toxic heavy metals, there remain contaminated natural water sources across the world. Herein we present a modular platform for developing selective sensors for toxic metal ions using N-substituted glycine, or peptoid, oligomers coupled to a fluorophore. As a preliminary evaluation of this strategy, structures based on previously identified metal-binding peptoids were synthesized with terminal pyrene moieties. Both derivatives of this initial design demonstrated a turn-off response in the presence of various metal ions...
March 25, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28240181/recent-advances-in-synthesis-and-identification-of-cyclic-peptides-for-bioapplications
#7
Yong Siang Ong, Liqian Gao, Karunakaran A Kalesh, Zhiqiang Yu, Jigang Wang, Chengcheng Liu, Yiwen Li, Hongyan Sun, Su Seong Lee
Cyclic peptides, owing to their good stability, high resistance to exo- and to some extent endo-peptidases, enhanced binding affinity and selectivity towards target biomolecules, are actively investigated as biochemical tools and therapeutic agents. In this review, we discuss various commonly utilized synthetic strategies for cyclic peptides and peptoids (peptidomimetics), their important screening methods to identify the bioactive cyclic peptides and peptoids such as combinatorial bead-based peptide library, phage display, mRNA display etc...
February 24, 2017: Current Topics in Medicinal Chemistry
https://www.readbyqxmd.com/read/28225627/1-2-3-triazolium-based-peptoid-oligomers
#8
Hafida Aliouat, Cécile Caumes, Olivier Roy, Mohamed Zouikri, Claude Taillefumier, Sophie Faure
The cis-directing effect of the 1,2,3-triazolium-type side chain was studied on dimeric peptoid models with various patterns: αα, αβ, βα and ββ. Low influences of the sequence and of the solvent were observed, the cis conformation of the amide carrying the triazolium ranging from 83 to 94% in proportion. The synthesis of peptoid homooligomers with four or eight pendant 1,2,3-triazolium side chains is described. α-, β- and α,β-peptoids carrying propargyl groups were subjected to CuAAC reaction using alkyl azides, and the resulting triazoles were quaternized providing well-defined multitriazolium platforms...
February 22, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28220538/on-bead-combinatorial-synthesis-and-imaging-of-europium-iii-based-paracest-agents-aids-in-identification-of-chemical-features-that-enhance-cest-sensitivity
#9
Jaspal Singh, Vineeta Rustagi, Shanrong Zhang, A Dean Sherry, D Gomika Udugamasooriya
The rate of water exchange between the inner sphere of a paramagnetic ion and bulk water is an important parameter in determining the magnitude of the chemical exchange saturation transfer signal from paramagnetic CEST agents (paraCEST). This is governed by various geometric, steric and ligand field factors created by macrocyclic ligands surrounding the paramagnetic metal ion. Our previous on-bead combinatorial studies of di-peptoid-europium(III)-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA)-tetraamide complexes revealed that negatively charged groups in the immediate vicinity of the metal center strongly enhances the CEST signal...
February 21, 2017: Magnetic Resonance in Chemistry: MRC
https://www.readbyqxmd.com/read/28195195/peptoids-successfully-inhibit-the-growth-of-gram-negative-e-coli-causing-substantial-membrane-damage
#10
Biljana Mojsoska, Gustavo Carretero, Sylvester Larsen, Ramona Valentina Mateiu, Håvard Jenssen
Peptoids are an alternative approach to antimicrobial peptides that offer higher stability towards enzymatic degradation. It is essential when developing new types of peptoids, that mimic the function of antimicrobial peptides, to understand their mechanism of action. Few studies on the specific mechanism of action of antimicrobial peptoids have been described in the literature, despite the plethora of studies on the mode of action of antimicrobial peptides. Here, we investigate the mechanism of action of two short cationic peptoids, rich in lysine and tryptophan side chain functionalities...
February 14, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28144675/self-assembly-of-ultra-small-micelles-from-amphiphilic-lipopeptoids
#11
King Hang Aaron Lau, Valeria Castelletto, Thomas Kendall, Jan Sefcik, Ian W Hamley, Mehedi Reza, Janne Ruokolainen
Poly(N-substituted glycine) "peptoids" constitute a promising class of peptide-mimetic materials. We introduce the self-assembly of lipopeptoids into spherical micelles ca. 5 nm in diameter as well as larger assemblies by varying the peptoid sequence design. Our results point to design rules for the self-assembly of peptoid nanostructures, enabling the creation of stable, ultra-small peptidomimetic nanospheres.
February 9, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28090689/%C3%AE-aminoxy-peptoids-a-unique-peptoid-backbone-with-a-preference-for-cis-amide-bonds
#12
Viktoria Krieger, Emanuele Ciglia, Roland Thoma, Vera Vasylyeva, Benedikt Frieg, Nader de Sousa Amadeu, Thomas Kurz, Christoph Janiak, Holger Gohlke, Finn K Hansen
α-Peptoids, or N-substituted glycine oligomers, are an important class of peptidomimetic foldamers with proteolytic stability. Nevertheless, the presence of cis/trans-amide bond conformers, which contribute to the high flexibility of α-peptoids, is considered as a major drawback. A modified peptoid backbone with an improved control of the amide bond geometry could therefore help to overcome this limitation. Herein, we have performed the first thorough analysis of the folding propensities of α-aminoxy peptoids (or N-substituted 2-aminoxyacetic acid oligomers)...
March 13, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28052595/lysine-based-%C3%AE-peptide-%C3%AE-peptoid-peptidomimetics-influence-of-hydrophobicity-fluorination-and-distribution-of-cationic-charge-on-antimicrobial-activity-and-cytotoxicity
#13
Natalia Molchanova, Paul R Hansen, Peter Damborg, Hanne M Nielsen, Henrik Franzyk
Multidrug-resistant bacteria pose a serious threat to public health worldwide. Previously, α-peptide/β-peptoid hybrid oligomers were found to display activity against Gram-negative multidrug-resistant bacteria. In the present work, the influence of hydrophobicity, fluorination, and distribution of cationic/hydrophobic residues on antimicrobial, hemolytic, and cytotoxic properties of α-peptide/β-peptoid hybrids were investigated. An array of 22 peptidomimetics was tested. Analogues with enhanced hydrophobicity were found to exhibit increased activity against Gram-positive bacteria...
January 4, 2017: ChemMedChem
https://www.readbyqxmd.com/read/27994753/discovery-and-characterization-of-a-peptoid-with-antifungal-activity-against-cryptococcus-neoformans
#14
Ashley E Corson, Scott A Armstrong, Matthew E Wright, Erin E McClelland, Kevin L Bicker
Studies show there is an increasing rate of fungal infections, especially in immunocompromised patients and treatments for fungal genera, such as Aspergillus, Candida, and Cryptococcus, carry significant cytotoxicity with an increasing prevalence of antifungal resistance. We have previously reported a high-throughput assay for identifying peptoids with antimicrobial properties from combinatorial libraries. Here we report the application of this assay in identifying a peptoid with antifungal properties against Cryptococcus neoformans...
December 8, 2016: ACS Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/27900840/peptoid-efficacy-against-polymicrobial-biofilms-determined-by-using-propidium-monoazide-modified-quantitative-pcr
#15
Yu Luo, Hannah L Bolt, Gabriela A Eggimann, Danny F McAuley, Ronan McMullan, Tanya Curran, Mei Zhou, Professor Colin A B Jahoda, Steven L Cobb, Fionnuala T Lundy
Biofilms containing Candida albicans are responsible for a wide variety of clinical infections. The protective effects of the biofilm matrix, the low metabolic activity of microorganisms within a biofilm and their high mutation rate, significantly enhance the resistance of biofilms to conventional antimicrobial treatments. Peptoids are peptide-mimics that share many features of host defence antimicrobial peptides but have increased resistance to proteases and therefore have better stability in vivo. The activity of a library of peptoids was tested against monospecies and polymicrobial bacterial/fungal biofilms...
January 3, 2017: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/27891122/membrane-active-epithelial-keratin-6a-fragments-kamps-are-unique-human-antimicrobial-peptides-with-a-non-%C3%AE-%C3%AE-structure
#16
Judy T Y Lee, Guangshun Wang, Yu Tong Tam, Connie Tam
Antibiotic resistance is a pressing global health problem that threatens millions of lives each year. Natural antimicrobial peptides and their synthetic derivatives, including peptoids and peptidomimetics, are promising candidates as novel antibiotics. Recently, the C-terminal glycine-rich fragments of human epithelial keratin 6A were found to have bactericidal and cytoprotective activities. Here, we used an improved 2-dimensional NMR method coupled with a new protocol for structural refinement by low temperature simulated annealing to characterize the solution structure of these kerain-derived antimicrobial peptides (KAMPs)...
2016: Frontiers in Microbiology
https://www.readbyqxmd.com/read/27878155/spin-labelled-diketopiperazines-and-peptide-peptoid-chimera-by-ugi-multi-component-reactions
#17
Haider N Sultani, Haleh H Haeri, Dariush Hinderberger, Bernhard Westermann
For the first time, spin-labelled coumpounds have been obtained by isonitrile-based multi component reactions (IMCRs). The typical IMCR Ugi-protocols offer a simple experimental setup allowing structural variety by which labelled diketopiperazines (DKPs) and peptide-peptoid chimera have been synthesized. The reaction keeps the paramagnetic spin label intact and offers a simple and versatile route to a large variety of new and chemically diverse spin labels.
December 28, 2016: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/27844017/design-of-new-potent-htlv-1-protease-inhibitors-in-silico-study
#18
Mitra Kheirabadi, Javad Maleki, Safieh Soufian, Samaneh Hosseini
HTLV-1 and HIV-1 are two major causes for severe T-cell leukemia disease and acquired immune deficiency syndrome (AIDS). HTLV-1 protease, a member of aspartic acid protease family, plays important roles in maturation during virus replication cycle. The impairment of these proteases results in uninfectious HTLV-1virions.Similar to HIV-1protease deliberate mutations that confer drug resistance on HTLV-1 are frequently seen in this protease. Therefore, inhibition of HTLV-1 protease activity is expected to disrupt HTLV-1's ability to replicate and infect additional cells...
March 2016: Molecular Biology Research Communications
https://www.readbyqxmd.com/read/27823569/structural-determinants-in-the-binding-of-bb2-receptor-ligands-in-silico-x-ray-and-nmr-studies-in-pd176252-analogues
#19
Antonio Carrieri, Enza Lacivita, Benny Danilo Belviso, Rocco Caliandro, Piero Mastrorilli, Vito Gallo, Mauro Niso, Marcello Leopoldo
The mammalian bombesin receptor family comprises three G protein-coupled receptors: the neuromedin B receptor, the gastrin-releasing peptide receptor (BB2), and the bombesin receptor subtype 3. BB2 receptor plays a role in gastrointestinal functions; however, at present the role of this subtype in physiological and pathological conditions is unknown due to the lack of specific binders for all subclasses of bombesin receptors. Here, we present a study focused on the properties of the peptoid bombesin antagonist called PD176252, and other structural analogues with the aim to elucidate causes of their different affinity towards the BB2 receptor...
November 4, 2016: Current Topics in Medicinal Chemistry
https://www.readbyqxmd.com/read/27814593/design-synthesis-and-use-of-peptoids-in-the-diagnosis-and-treatment-of-cancer
#20
Arijit Bhowmik, Malini Basu, Mrinal K Ghosh
Genetic variations in cancer cells are the underpinning for the development of resistance and failure of the treatment by current anticancer drugs. Thus, an ideal drug must overcome failure of treatment and prevents development of drug resistance. There are a wide variety of emerging, easy to prepare and cost effective group of drugs that are collectively called peptoids or peptidomimetics. These new set of drugs exhibit distinct features including protease resistance, are non-immunogenic, do not hinder functionality and backbone polarity, and can adopt different conformations...
January 1, 2017: Frontiers in Bioscience (Elite Edition)
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