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Peptoid

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https://www.readbyqxmd.com/read/28225627/1-2-3-triazolium-based-peptoid-oligomers
#1
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
#2
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)-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
#3
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
#4
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
#5
Viktoria Krieger, Emanuele Ciglia, Roland Thoma, Vera Vasylyeva, Benedikt Frieg, Nader de Sousa Amadeu, Thomas Kurz, Christoph Janiak, Holger Gohlke, Finn Kristian 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. Here we have performed the first thorough analysis of the folding propensities of α-aminoxy peptoids (or N-substituted 2-aminoxyacetic acid oligomers)...
January 16, 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
#6
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
#7
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
#8
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
#9
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
#10
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
#11
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
#12
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
#13
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)
https://www.readbyqxmd.com/read/27812535/blood-biomarker-for-parkinson-disease-peptoids
#14
Umar Yazdani, Sayed Zaman, Linda S Hynan, L Steven Brown, Richard B Dewey, David Karp, Dwight C German
Parkinson disease (PD) is the second most common neurodegenerative disease. Because dopaminergic neuronal loss begins years before motor symptoms appear, a biomarker for the early identification of the disease is critical for the study of putative neuroprotective therapies. Brain imaging of the nigrostriatal dopamine system has been used as a biomarker for early disease along with cerebrospinal fluid analysis of α-synuclein, but a less costly and relatively non-invasive biomarker would be optimal. We sought to identify an antibody biomarker in the blood of PD patients using a combinatorial peptoid library approach...
2016: NPJ Parkinson's Disease
https://www.readbyqxmd.com/read/27805236/selective-complexation-of-divalent-cations-by-a-cyclic-%C3%AE-%C3%AE-peptoid-hexamer-a-spectroscopic-and-computational-study
#15
E De Santis, A A Edwards, B D Alexander, S J Holder, A-S Biesse-Martin, B V Nielsen, D Mistry, L Waters, G Siligardi, R Hussain, S Faure, C Taillefumier
We describe the qualitative and quantitative analysis of the complexation properties towards cations of a cyclic peptoid hexamer composed of alternating α- and β-peptoid monomers, which bear exclusively chiral (S)-phenylethyl side chains (spe) that have no noticeable chelating properties. The binding of a series of monovalent and divalent cations was assessed by (1)H NMR, circular dichroism, fluorescence and molecular modelling. In contrast to previous studies on cations binding by 18-membered α-cyclopeptoid hexamers, the 21-membered cyclopeptoid cP1 did not complex monovalent cations (Na(+), K(+), Ag(+)) but showed selectivity for divalent cations (Ca(2+), Ba(2+), Sr(2+) and Mg(2+))...
December 7, 2016: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/27794618/molecular-engineering-of-the-peptoid-nanosheet-hydrophobic-core
#16
Ellen J Robertson, Caroline Proulx, Jessica K Su, Rita L Garcia, Stan Yoo, Eric M Nehls, Michael D Connolly, Laudann Taravati, Ronald N Zuckermann
The relationship between the structure of sequence-defined peptoid polymers and their ability to assemble into well-defined nanostructures is important to the creation of new bioinspired platforms with sophisticated functionality. Here, the hydrophobic N-(2-phenylethyl)glycine (Npe) monomers of the standard nanosheet-forming peptoid sequence were modified in an effort to (1) produce nanosheets from relatively short peptoids, (2) inhibit the aggregation of peptoids in bulk solution, (3) increase nanosheet stability by promoting packing interactions within the hydrophobic core, and (4) produce nanosheets with a nonaromatic hydrophobic core...
November 15, 2016: Langmuir: the ACS Journal of Surfaces and Colloids
https://www.readbyqxmd.com/read/27794613/structure-rheology-relationship-in-nanosheet-forming-peptoid-monolayers
#17
Ellen J Robertson, Eric Michael Nehls, Ronald N Zuckermann
Peptoid nanosheets are novel protein-mimetic materials that form from the supramolecular assembly of sequence-defined peptoid polymers. The component polymer chains organize themselves via a unique mechanism at the air-water interface, in which the collapse of a compressed peptoid monolayer results in free-floating, bilayer nanosheets. To impart functionality into these bilayer materials, structural engineering of the nanosheet-forming peptoid strand is necessary. We previously synthesized a series of peptoid analogues with modifications to the hydrophobic core in order to probe the nanosheet tolerance to different packing interactions...
November 22, 2016: Langmuir: the ACS Journal of Surfaces and Colloids
https://www.readbyqxmd.com/read/27793068/cyclization-improves-membrane-permeation-by-antimicrobial-peptoids
#18
Konstantin Andreev, Michael W Martynowycz, Andrey Ivankin, Mia L Huang, Ivan Kuzmenko, Mati Meron, Binhua Lin, Kent Kirshenbaum, David Gidalevitz
The peptidomimetic approach has emerged as a powerful tool for overcoming the inherent limitations of natural antimicrobial peptides, where the therapeutic potential can be improved by increasing the selectivity and bioavailability. Restraining the conformational flexibility of a molecule may reduce the entropy loss upon its binding to the membrane. Experimental findings demonstrate that the cyclization of linear antimicrobial peptoids increases their bactericidal activity against Staphylococcus aureus while maintaining high hemolytic concentrations...
December 6, 2016: Langmuir: the ACS Journal of Surfaces and Colloids
https://www.readbyqxmd.com/read/27776890/modulating-amyloid-%C3%AE-aggregation-the-effects-of-peptoid-side-chain-placement-and-chirality
#19
J Phillip Turner, Shelby E Chastain, Dongwon Park, Melissa A Moss, Shannon L Servoss
Alzheimer's disease (AD) is characterized by the buildup of insoluble aggregated amyloid-β protein (Aβ) into plaques that accumulate between the neural cells in the brain. AD is the sixth leading cause of death in the United States and is the only cause of death among the top ten that cannot currently be treated or cured (Alzheimer's Association, 2011; Selkoe, 1996). Researchers have focused on developing small molecules and peptides to prevent Aβ aggregation; however, while some compounds appear promising in vitro, the research has not resulted in a viable therapeutic treatment...
January 1, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/27756123/a-thermodynamic-description-of-the-adsorption-of-simple-water-soluble-peptoids-to-silica
#20
Anna L Calkins, Jennifer Yin, Jacenda L Rangel, Madeleine R Landry, Amelia A Fuller, Grace Y Stokes
The first report of a water-soluble peptoid adsorbed to silica monitored by second harmonic generation (SHG) at the liquid/solid interface is presented here. The molecular insights gained from these studies will inform the design and preparation of novel peptoid coatings. Simple 6- and 15-residue peptoids were dissolved in phosphate buffered saline and adsorbed to bare silica surfaces. Equilibrium binding constants and relative surface concentrations of adsorbed peptoids were determined from fits to the Langmuir model...
November 8, 2016: Langmuir: the ACS Journal of Surfaces and Colloids
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