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https://www.readbyqxmd.com/read/29164219/conformational-isomerism-in-cyclic-peptoids-and-its-specification
#1
A D'Amato, R Schettini, G Della Sala, C Costabile, C Tedesco, I Izzo, F De Riccardis
Most of the structural studies made on the secondary structure of peptoids describe their geometric attributes in terms of the classic Ramachandran plot (based on the local analysis of ω, ψ, χ, φ dihedral angles). However, little intuitive understanding is available from internal coordinates when stereochemistry is involved. In this contribution we list all the conformationally stable cyclic peptoids reported up to the year 2017 and propose a simple method to define their geometric arrangement in terms of planar chirality...
November 22, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/29161507/development-of-spiroligomer-peptoid-hybrids
#2
Justin D Northrup, Giulia Mancini, Claire R Purcell, Christian E Schafmeister
Creating functional macromolecules that possess the diversity and functionality of proteins poses an enormous challenge, as this requires large, preorganized macromolecules to facilitate interactions. Peptoids have been shown to interact with proteins, and combinatorial libraries of peptoids have been useful in discovering new ligands for protein binding. We have created spiroligomer-peptoid hybrids that have a spirocyclic core that preorganizes functional groups in three-dimensional space. By utilizing spiroligomers, we can reduce the number of rotatable bonds between functional groups, while increasing the stereochemical diversity of the molecules...
November 21, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/29119173/control-of-porphyrin-interactions-via-structural-changes-of-a-peptoid-scaffold
#3
Woojin Yang, Boyeong Kang, Vincent A Voelz, Jiwon Seo
Nature utilizes optimally organized pigments in light-harvesting complexes. To mimic the natural photosynthetic proteins, effective control over inter-pigment interactions is necessary to attain the desired photophysical properties. Previously, we developed porphyrin-peptoid conjugates (PPCamide) and displayed two porphyrins at defined positions on an α-helical peptoid using a flexible n-butyl linker. Herein, we synthesized new porphyrin-peptoid conjugates (PPCC-C), where porphyrins are conjugated through a rigid C-C linkage to the helical peptoid via the Suzuki-Miyaura cross-coupling reaction...
November 22, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/29052913/a-pure-polyproline-type-i-like-peptoid-helix-via-metal-coordination
#4
Galia Maayan, Lieby Zborovsky, Alisa Smolyakova, Maria Baskin
Peptoids, N-substituted glycine oligomers, are an important class of foldamers that can adopt polyproline type helices (PP-I and PP-II), given that the majority of their sequence consists of chiral bulky side chains. Herein we introduce a new approach for the stabilization of a pure PP-I-like peptoid helix via metal coordination. We performed a systematic spectroscopic study on a series of peptoid heptamers baring two 8-hydroxyquinoline ligands at fixed positions, and a mixture of chiral phenyl and alkyl substituents in varied positions along the peptoid backbone...
October 20, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/29045152/discovery-of-potent-and-orally-bioavailable-macrocyclic-peptide-peptoid-hybrid-cxcr7-modulators
#5
Markus Boehm, Kevin Beaumont, Rhys Jones, Amit S Kalgutkar, Liying Zhang, Karen Atkinson, Guoyun Bai, Janice A Brown, Heather Eng, Gilles H Goetz, Brian R Holder, Bhagyashree Khunte, Sarah Lazzaro, Chris Limberakis, Sangwoo Ryu, Michael J Shapiro, Laurie Tylaska, Jiangli Yan, Rushia Turner, Siegfried S F Leung, Mahesh Ramaseshan, David A Price, Spiros Liras, Matthew P Jacobson, David J Earp, R Scott Lokey, Alan M Mathiowetz, Elnaz Menhaji-Klotz
The chemokine receptor CXCR7 is an attractive target for a variety of diseases. While several small-molecule modulators of CXCR7 have been reported, peptidic macrocycles may provide advantages in terms of potency, selectivity, and reduced off-target activity. We produced a series of peptidic macrocycles that incorporate an N-linked peptoid functionality where the peptoid group enabled us to explore side-chain diversity well beyond that of natural amino acids. At the same time, theoretical calculations and experimental assays were used to track and reduce the polarity while closely monitoring the physicochemical properties...
October 30, 2017: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/29039680/solid-phase-synthesis-of-%C3%AE-peptoids-with-chiral-backbone-substituents-using-reductive-amination
#6
Jumpei Morimoto, Yasuhiro Fukuda, Shinsuke Sando
A new submonomeric synthetic method of β-peptoids that allows introduction of chiral backbone substituents is established. The synthesis of β-peptoids with various backbone substituents on β-carbons and spectroscopic studies of synthesized oligomers are described.
October 17, 2017: Organic Letters
https://www.readbyqxmd.com/read/29035526/interplay-among-sequence-folding-propensity-and-bio-piezoelectric-response-in-short-peptides-and-peptoids
#7
Christopher W Marvin, Haley M Grimm, Nathaniel C Miller, W Seth Horne, Geoffrey R Hutchison
Many biomaterials are piezoelectric (i.e., mechanically deform under an applied electric field); however, the molecular origin of this phenomenon remains unclear. In the case of protein-based scaffolds, one possibility involves flexible response of local folding motifs to the applied field. Here, we test this hypothesis by examining the piezoresponse in a series of helical peptide-based oligomers. Control over folding propensity is exerted through systematic variation in both side-chain sequence and backbone composition...
October 30, 2017: Journal of Physical Chemistry. B
https://www.readbyqxmd.com/read/28870843/phosphatidylserine-a-cancer-cell-targeting-biomarker
#8
REVIEW
Bhupender Sharma, Shamsher S Kanwar
Cancer is a leading cause of mortality and morbidity globally. Many prominent cancer-associated molecules have been identified over the recent years which include EGFR, CD44, TGFbRII, HER2, miR-497, NMP22, BTA, Fibrin/FDP etc. These biomarkers are often used for screening, detection, diagnosis, prognosis, prediction and monitoring of cancer development. Phosphatidylserine (PS) is an essential component in all human cells which is present on the inner leaflet of the cell membrane. The oxidative stress causes exposure of PS on the surface of the vascular endothelium in the cancer cells (lung, breast, pancreatic, bladder, skin, brain metastasis, rectal adenocarcinoma etc...
September 1, 2017: Seminars in Cancer Biology
https://www.readbyqxmd.com/read/28852829/pal-12-a-new-anti-aging-hexa-peptoid-inhibits-uvb-induced-photoaging-in-human-dermal-fibroblasts-and-3d-reconstructed-human-full-skin-model-keraskin-ft%C3%A2
#9
Daeun Song, Hyeonji Park, Su-Hyon Lee, Mi Jung Kim, Eun-Joo Kim, Kyung-Min Lim
Peptoids are a class of peptidomimetics whose pharmacological activities are widely investigated owing to their remarkable biological stability. However, the utilities of peptoids as cosmetic functional ingredients have not been fully explored. Here, we investigated anti-aging effects of PAL-12, a new hexa-peptoid, on UVB-induced photoaging in human dermal fibroblasts (HDFs) and a 3D reconstituted human full skin model, Keraskin-FT™. PAL-12 suppressed matrix metalloproteinase-1 (MMP-1) expression induced by UVB irradiation along with the attenuation of MMP-1 secretion as determined by ELISA assay...
November 2017: Archives of Dermatological Research
https://www.readbyqxmd.com/read/28837348/homogeneous-and-robust-polyproline-type-i-helices-from-peptoids-with-nonaromatic-%C3%AE-chiral-side-chains
#10
Olivier Roy, Geoffrey Dumonteil, Sophie Faure, Laurent Jouffret, Alexandre Kriznik, Claude Taillefumier
Peptoids that are oligomers of N-substituted glycines represent a class of peptide mimics with great potential in areas ranging from medicinal chemistry to biomaterial science. Controlling the equilibria between the cis and trans conformations of their backbone amides is the major hurdle to overcome for the construction of discrete folded structures, particularly for the development of all-cis polyproline type I (PPI) helices, as tools for modulating biological functions. The prominent role of backbone to side chain electronic interactions (n → π*) and side chains bulkiness in promoting cis-amides was essentially investigated with peptoid aromatic side chains, among which the chiral 1-naphthylethyl (1npe) group yielded the best results...
September 19, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28837260/a-selective-biligand-inhibitor-of-ck2-increases-caspase-3-activity-in-cancer-cells-and-inhibits-platelet-aggregation
#11
Hedi Rahnel, Kaido Viht, Darja Lavogina, Olga Mazina, Tõiv Haljasorg, Erki Enkvist, Asko Uri
Cancer cells express high levels of CK2, and its inhibition leads to apoptosis. CK2 has therefore emerged as a new drug target for cancer therapy. A biligand inhibitor ARC-772 was constructed by conjugating 4-(2-amino-1,3-thiazol-5-yl)benzoic acid and a carboxylate-rich peptoid. ARC-772 was found to bind CK2 with a Kd value of 0.3 nm and showed remarkable CK2 inhibitory selectivity in a panel of 140 protein kinases (Gini coefficient: 0.75 at c=100 nm). ARC-775, the acetoxymethyl ester prodrug of ARC-772, was efficiently taken up by cells...
October 20, 2017: ChemMedChem
https://www.readbyqxmd.com/read/28822292/nanoparticles-assemblies-on-demand-controlled-aggregation-of-ag-0-mediated-by-modified-peptoid-sequences
#12
Hagar Tigger-Zaborov, Galia Maayan
Assemblies of metal nanoparticles (NPs) have been broadly used for the construction of materials with distinct spectroscopic properties towards sensing applications. On the other hand, well-dispersed NPs are exploit for applications in catalysis and medicine. Biopolymers or biomimetic oligomers can serve both as efficient stabilizers of NPs and as useful aggregation mediators that can lead to assemblies with unique properties. Controlling aggregation processes, however, is still challenging and often relies on trial and error rather than on defined thumb rules...
August 12, 2017: Journal of Colloid and Interface Science
https://www.readbyqxmd.com/read/28808293/targeting-apolipoprotein-e-amyloid-%C3%AE-binding-by-peptoid-cpo_a%C3%AE-17-21%C3%A2-p-ameliorates-alzheimer-s-disease-related-pathology-and-cognitive-decline
#13
Shan Liu, Shinae Park, Grant Allington, Frances Prelli, Yanjie Sun, Mitchell Martá-Ariza, Henrieta Scholtzova, Goutam Biswas, Bernard Brown, Philip B Verghese, Pankaj D Mehta, Yong-Uk Kwon, Thomas Wisniewski
Inheritance of the apolipoprotein E4 (apoE4) genotype has been identified as the major genetic risk factor for late onset Alzheimer's disease (AD). Studies have shown that apoE, apoE4 in particular, binds to amyloid-β (Aβ) peptides at residues 12-28 of Aβ and this binding modulates Aβ accumulation and disease progression. We have previously shown in several AD transgenic mice lines that blocking the apoE/Aβ interaction with Aβ12-28 P reduced Aβ and tau-related pathology, leading to cognitive improvements in treated AD mice...
August 14, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28763612/cyclic-peptoids-as-mycotoxin-mimics-an-exploration-of-their-structural-and-biological-properties
#14
Assunta D'Amato, Raffaele Volpe, Maria Carmela Vaccaro, Stefania Terracciano, Ines Bruno, Massimo Tosolini, Consiglia Tedesco, Giovanni Pierri, Paolo Tecilla, Chiara Costabile, Giorgio Della Sala, Irene Izzo, Francesco De Riccardis
Cyclic peptoids have recently emerged as important examples of peptidomimetics for their interesting complexing properties and innate ability to permeate biological barriers. In the present contribution, experimental and theoretical data evidence the intricate conformational and stereochemical properties of five novel hexameric peptoids decorated with N-isopropyl, N-isobutyl, and N-benzyl substituents. Complexation studies by NMR, in the presence of sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (NaTFPB), theoretical calculations, and single-crystal X-ray analyses indicate that the conformationally stable host/guest metal adducts display architectural ordering comparable to that of the enniatins and beauvericin mycotoxins...
August 17, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28735540/the-n%C3%A2-%C3%AF-interaction
#15
Robert W Newberry, Ronald T Raines
The carbonyl group holds a prominent position in chemistry and biology not only because it allows diverse transformations but also because it supports key intermolecular interactions, including hydrogen bonding. More recently, carbonyl groups have been found to interact with a variety of nucleophiles, including other carbonyl groups, in what we have termed an n→π* interaction. In an n→π* interaction, a nucleophile donates lone-pair (n) electron density into the empty π* orbital of a nearby carbonyl group...
August 15, 2017: Accounts of Chemical Research
https://www.readbyqxmd.com/read/28700225/combining-elements-from-two-antagonists-of-formyl-peptide-receptor-2-generates-more-potent-peptidomimetic-antagonists
#16
Sarah Line Skovbakke, André Holdfeldt, Christina Nielsen, Anna Mette Hansen, Iris Perez-Gassol, Claes Dahlgren, Huamei Forsman, Henrik Franzyk
Structural optimization of a peptidomimetic antagonist of formyl peptide receptor 2 (FPR2) was explored by an approach involving combination of elements from the two most potent FPR2 antagonists described: a Rhodamine B-conjugated 10-residue gelsonin-derived peptide (i.e., PBP10, RhB-QRLFQVKGRR-OH) and the palmitoylated α-peptide/β-peptoid hybrid Pam-(Lys-βNspe)6-NH2. This generated an array of hybrid compounds from which a new subclass of receptor-selective antagonists was identified. The most potent representatives displayed activity in the low nanomolar range...
August 24, 2017: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28684782/precisely-tuneable-energy-transfer-system-using-peptoid-helix-based-molecular-scaffold
#17
Boyeong Kang, Woojin Yang, Sebok Lee, Sudipto Mukherjee, Jonathan Forstater, Hanna Kim, Byoungsook Goh, Tae-Young Kim, Vincent A Voelz, Yoonsoo Pang, Jiwon Seo
The energy flow during natural photosynthesis is controlled by maintaining the spatial arrangement of pigments, employing helices as scaffolds. In this study, we have developed porphyrin-peptoid (pigment-helix) conjugates (PPCs) that can modulate the donor-acceptor energy transfer efficiency with exceptional precision by controlling the relative distance and orientation of the two pigments. Five donor-acceptor molecular dyads were constructed using zinc porphyrin and free base porphyrin (Zn(i + 2)-Zn(i + 6)), and highly efficient energy transfer was demonstrated with estimated efficiencies ranging from 92% to 96% measured by static fluorescence emission in CH2Cl2 and from 96...
July 6, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28656750/ultrafast-set-lrp-with-peptoid-cytostatic-drugs-as-monofunctional-and-bifunctional-initiators
#18
Gerard Lligadas, Mojtaba Enayati, Silvia Grama, Rauan Smail, Samuel E Sherman, Virgil Percec
To continue expanding the use of Single Electron Transfer-Living Radical Polymerization (SET-LRP) in applications at the interface between macromolecular science, biomacromolecules, biology and medicine, it is essential to develop novel initiators that do not compromise the structural stability of synthesized polymers in biological environments. Here, we report that stable 2-bromopropionyl peptoid-type initiators such as 1,4-bis(2-bromopropionyl)piperazine and 4-(2-bromopropionyl)morpholine are an alternative that meets the standards reached by the well-known secondary and tertiary α-haloester-type initiators in terms of excellent control over molecular weight evolution and distribution as well as polymer chain ends...
July 10, 2017: Biomacromolecules
https://www.readbyqxmd.com/read/28652236/synthetic-cyclic-peptomers-as-type-iii-secretion-system-inhibitors
#19
Hanh Lam, Joshua Schwochert, Yongtong Lao, Tannia Lau, Cameron Lloyd, Justin Luu, Olivia Kooner, Jessica Morgan, Scott Lokey, Victoria Auerbuch
Antibiotic-resistant bacteria are an emerging threat to global public health. New classes of antibiotics and tools for antimicrobial discovery are urgently needed. Type III secretion systems (T3SS), which are required by dozens of Gram-negative bacteria for virulence but largely absent from nonpathogenic bacteria, are promising virulence blocker targets. The ability of mammalian cells to recognize the presence of a functional T3SS and trigger NF-κB activation provides a rapid and sensitive method for identifying chemical inhibitors of T3SS activity...
September 2017: Antimicrobial Agents and Chemotherapy
https://www.readbyqxmd.com/read/28605073/antibody-mimetic-peptoid-nanosheet-for-label-free-serum-based-diagnosis-of-alzheimer-s-disease
#20
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...
August 2017: Advanced Materials
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