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https://www.readbyqxmd.com/read/28605073/antibody-mimetic-peptoid-nanosheet-for-label-free-serum-based-diagnosis-of-alzheimer-s-disease
#1
Ling Zhu, Zijian Zhao, Peng Cheng, Zhaohui He, Zhiqiang Cheng, Jiaxi Peng, Huayi Wang, Chen Wang, Yanlian Yang, Zhiyuan Hu
Alzheimer's disease (AD) is the most common form of dementia characterized by progressive cognitive decline. Current diagnosis of AD is based on symptoms, neuropsychological tests, and neuroimaging, and is usually evident years after the pathological process. Early assessment at the preclinical or prodromal stage is in a great demand since treatment after the onset can hardly stop or reverse the disease progress. However, early diagnosis of AD is challenging due to the lack of reliable noninvasive approaches...
June 12, 2017: Advanced Materials
https://www.readbyqxmd.com/read/28574690/design-multicomponent-synthesis-and-anticancer-activity-of-a-focused-histone-deacetylase-hdac-inhibitor-library-with-peptoid-based-cap-groups
#2
Viktoria Krieger, Alexandra Hamacher, Christoph G W Gertzen, Johanna Senger, Martijn R H Zwinderman, Martin Marek, Christophe Romier, Frank J Dekker, Thomas Kurz, Manfred Jung, Holger Gohlke, Matthias U Kassack, Finn K Hansen
In this work, we report the multicomponent synthesis of a focused histone deacetylase (HDAC) inhibitor library with peptoid-based cap groups and different zinc-binding groups. All synthesized compounds were tested in a cellular HDAC inhibition assay and a MTT assay for cytotoxicity. Based on their noteworthy activity in the cellular HDAC assay, four compounds were further screened for their inhibitory activity against recombinant HDAC1-3, HDAC6, and HDAC8. All four compounds showed potent inhibition of HDAC1-3 as well as significant inhibition of HDAC6 with IC50 values in the submicromolar concentration range...
June 2, 2017: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28572550/synthesis-crystallization-x-ray-structural-characterization-and-solid-state-assembly-of-a-cyclic-hexapeptoid-with-propargyl-and-methoxyethyl-side-chains
#3
Consiglia Tedesco, Eleonora Macedi, Alessandra Meli, Giovanni Pierri, Giorgio Della Sala, Christina Drathen, Andrew N Fitch, Gavin B M Vaughan, Irene Izzo, Francesco De Riccardis
The synthesis and the structural characterization of a cyclic hexapeptoid with four methoxyethyl and two propargyl side chains have disclosed the presence of a hydrate crystal form [form (I)] and an anhydrous crystal form [form (II)]. The relative amounts of form (I) and form (II) in the as-purified product were determined by Rietveld refinement and depend on the purification procedures. In crystal form (I), peptoid molecules assemble in a columnar arrangement by means of side-chain-to-backbone C=CH...OC hydrogen bonds...
June 1, 2017: Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials
https://www.readbyqxmd.com/read/28551176/a-unique-mid-sequence-linker-used-to-multimerize-the-lipid-phosphatidylserine-ps-binding-peptide-peptoid-hybrid-pps1
#4
Satya Prakash Shukla, Joseph C Manarang, D Gomika Udugamasooriya
Ligand multimerizations enhance the binding affinity towards cell surface biomarkers through their avidity effects. Typical linkers connect individual monomeric ligand moieties from one end (e.g., C- or N-terminus of a peptide) and exclusively target protein receptors. The lipid phosphatidylserine (PS) is normally present on the cytoplasmic side of the eukaryotic cell membrane, but in tumors and tumor endothelial cells, this negatively charged PS flips to the outer layer. We recently reported a PS binding peptide-peptoid hybrid (PPS1) that has distinct positively charged and hydrophobic residue-containing regions...
May 19, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28537738/a-peptoid-square-helix-via-synergistic-control-of-backbone-dihedral-angles
#5
Benjamin C Gorske, Emily M Mumford, Charles G Gerrity, Imelda Ko
The continued expansion of the fields of macromolecular chemistry and nanoscience has motivated the development of new secondary structures that can serve as architectural elements of innovative materials, molecular machines, biological probes, and even commercial medicines. Synthetic foldamers are particularly attractive systems for developing such elements because they are specifically designed to facilitate synthetic manipulation and functional diversity. However, relatively few predictive design principles exist that permit both rational and modular control of foldamer secondary structure, while maintaining the capacity for facile diversification of displayed functionality...
June 21, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28533975/an-exhaustive-survey-of-regular-peptide-conformations-using-a-new-metric-for-backbone-handedness-h
#6
Ranjan V Mannige
The Ramachandran plot is important to structural biology as it describes a peptide backbone in the context of its dominant degrees of freedom-the backbone dihedral angles φ and ψ (Ramachandran, Ramakrishnan & Sasisekharan, 1963). Since its introduction, the Ramachandran plot has been a crucial tool to characterize protein backbone features. However, the conformation or twist of a backbone as a function of φ and ψ has not been completely described for both cis and trans backbones. Additionally, little intuitive understanding is available about a peptide's conformation simply from knowing the φ and ψ values of a peptide (e...
2017: PeerJ
https://www.readbyqxmd.com/read/28513982/plasmon-enhanced-fluorescence-based-on-porphyrin-peptoid-hybridized-gold-nanoparticle-platform
#7
Younghye Kim, Boyeong Kang, Hyo-Yong Ahn, Jiwon Seo, Ki Tae Nam
A porphyrin-peptoid-hybridized silica-coated gold nanoparticle is developed, which is inspired by the protein-chlorophyll ensemble found in photosynthetic antenna. In the natural antenna, chlorophylls are integrated into dense assemblies that are supported by frameworks of proteins, which ensure optimal pigment arrangement for effective light harvesting. In the subject platform, porphyrins are conjugated to the peptoid helix scaffold in a structurally well-defined alignments and subsequently immobilized on the surface of nanoparticles...
May 17, 2017: Small
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
#8
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 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
#9
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...
May 3, 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
#10
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
#11
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
#12
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
#13
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
#14
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
#15
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
#16
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
#17
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
#18
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
#19
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
#20
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...
February 20, 2017: ChemMedChem
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