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Helical cell penetrating peptide

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https://www.readbyqxmd.com/read/29090725/arginine-modification-of-lycosin-i-to-improve-inhibitory-activity-against-cancer-cells
#1
Peng Zhang, Jing Ma, Yujie Yan, Bo Chen, Bobo Liu, Cui Jian, Baode Zhu, Songping Liang, Youlin Zeng, Zhonghua Liu
Lycosin-I is a linear amphipathic α-helical anticancer peptide (ACP) extracted from the spider Lycosa singoriensis, which can activate the mitochondrial death pathway to induce apoptosis in tumor cells and up-regulate p27 to inhibit cell proliferation. However, the applicability of lycosin-I as a novel anticancer drug is limited by its low cellular entry and efficacy in solid tumors. Amino acid substitution presents an effective and modest strategy to improve the anticancer activity and bioavailability of ACPs...
November 15, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/29073092/unique-amalgamation-of-primary-and-secondary-structural-elements-transform-peptaibols-into-potent-bioactive-cell-penetrating-peptides
#2
Lin Du, April L Risinger, Carter A Mitchell, Jianlan You, Blake W Stamps, Ning Pan, Jarrod B King, Jean C Bopassa, Susan I V Judge, Zhibo Yang, Bradley S Stevenson, Robert H Cichewicz
Mass-spectrometry-based metabolomics and molecular phylogeny data were used to identify a metabolically prolific strain of Tolypocladium that was obtained from a deep-water Great Lakes sediment sample. An investigation of the isolate's secondary metabolome resulted in the purification of a 22-mer peptaibol, gichigamin A (1). This peptidic natural product exhibited an amino acid sequence including several β-alanines that occurred in a repeating ααβ motif, causing the compound to adopt a unique right-handed 311 helical structure...
October 24, 2017: Proceedings of the National Academy of Sciences of the United States of America
https://www.readbyqxmd.com/read/29045142/measuring-intracellular-secondary-structure-of-a-cell-penetrating-peptide-in-situ
#3
Frederik Fleissner, Sabine Pütz, Mischa Schwendy, Mischa Bonn, Sapun H Parekh
Cell-penetrating peptides (CPPs) are short peptide sequences that can translocate across cellular plasma membranes and are thus potential delivery vectors for diagnostic and therapeutic applications. Many CPPs exhibit some sort of structural polymorphism, where the secondary structure of the peptide is altered strongly by its local environment, which is believed to facilitate membrane translocation and uptake. However, much less is known about the fate and structure of CPPs within cells largely due to measurement difficulty...
November 7, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28921993/lactam-stapled-cell-penetrating-peptides-cell-uptake-and-membrane-binding-properties
#4
Marco J Klein, Samuel Schmidt, Parvesh Wadhwani, Jochen Bürck, Johannes Reichert, Sergii Afonin, Marina Berditsch, Tim Schober, Roland Brock, Manfred Kansy, Anne S Ulrich
Stapling of side chains to stabilize an α-helical structure has been generally associated with an increased uptake of CPPs. Here, we compare four amphiphilic stapled peptides with their linear counterparts in terms of their membrane binding and conformational features in order to correlate these with uptake efficiency and toxicological effects. The impact of lactam stapling was found to vary strongly with regard to the different aspects of peptide-membrane interactions. Nearly all stapled peptides caused less membrane perturbation (vesicle leakage, hemolysis, bacterial lysis) than their linear counterparts...
October 12, 2017: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28885830/oligoprolines-as-molecular-entities-for-controlling-distance-in-biological-and-material-sciences
#5
Stefanie Dobitz, Matthew R Aronoff, Helma Wennemers
Nature utilizes large biomolecules to fulfill tasks that require spatially well-defined arrangements at the molecular level such as electron transfer, ligand-receptor interactions, or catalysis. The creation of synthetic molecules that enable precise control over spacing and functionalization provides opportunities across diverse disciplines. Key requirements of functionalizable oligomeric scaffolds include the specific control of their molecular properties where the correct balance of flexibility and rigidity must be maintained in addition to the prerequisite of defined length...
October 17, 2017: Accounts of Chemical Research
https://www.readbyqxmd.com/read/28876512/effect-of-stapling-architecture-on-physiochemical-properties-and-cell-permeability-of-stapled-%C3%AE-helical-peptides-a-comparative-study
#6
Yuan Tian, Yanhong Jiang, Jingxu Li, Dongyuan Wang, Hui Zhao, Zigang Li
Stapled peptides have emerged as a new class of targeting molecules with high binding affinity and specificity for intracellular undruggable targets. Their ability to penetrate cell membranes is exceptionally intriguing but remains elusively and controversially discussed. To understand the effect of stapling architectures on their physiochemical properties and to aid in promoting their cell permeability, we report herein a comparative study on the physiochemical properties and cell permeability of stapled α-helical peptides with different types of crosslinks...
September 6, 2017: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/28828981/the-primary-mechanism-of-cellular-internalization-for-a-short-cell-penetrating-peptide-as-a-nano-scale-delivery-system
#7
Betty R Liu, Yue-Wern Huang, Mallikarjuna Korivi, Shih-Yen Lo, Robert S Aronstam, Han-Jung Lee
BACKGROUND: Development of effective drug delivery systems (DDS) is a critical issue in health care and medicine. Advances in molecular biology and nanotechnology have allowed the introduction of nanomaterial-based drug delivery systems. Cell-penetrating peptides (CPPs) can form the basis of drug delivery systems by virtue of their ability to support the transport of cargoes into the cell. Potential cargoes include proteins, DNA, RNA, liposomes, and nanomaterials. These cargoes generally retain their bioactivities upon entering cells...
2017: Current Pharmaceutical Biotechnology
https://www.readbyqxmd.com/read/28741867/targeting-of-a-helix-loop-helix-transcriptional-regulator-by-a-short-helical-peptide
#8
Cornelia Roschger, Saskia Neukirchen, Brigitta Elsässer, Mario Schubert, Nicole Maeding, Thomas Verwanger, Barbara Krammer, Chiara Cabrele
The Id proteins (Id1-4) are cell-cycle regulators that play a key role during development, in cancer and vascular disorders. They contain a conserved helix-loop-helix (HLH) domain that folds into a parallel four-helix bundle upon self- or hetero-association with basic-HLH transcription factors. By using such protein-protein interactions, the Id proteins inhibit cell differentiation and promote cell-cycle progression. Accordingly, their supporting role in cancer has been convincingly demonstrated, which makes these proteins interesting therapeutic targets...
September 21, 2017: ChemMedChem
https://www.readbyqxmd.com/read/28636317/downsizing-proto-oncogene-cfos-to-short-helix-constrained-peptides-that-bind-jun
#9
Daniel Baxter, Samuel R Perry, Timothy A Hill, W Mei Kok, Nathan R Zaccai, R Leo Brady, David P Fairlie, Jody M Mason
The oncogenic transcription factor activator protein-1 (AP-1) is a DNA-binding protein that assembles through dimerization of Fos and Jun protein subunits, their leucine-rich helical sequences entwining into a coiled-coil structure. This study reports on downsizing the proto-oncogene cFos protein (380 residues) to shorter peptides (37-25 residues) modified with helix-inducing constraints to enhance binding to Jun. A crystal structure is reported for a 37-residue Fos-derived peptide (FosW) bound to Jun. This guided iterative downsizing of FosW to shorter peptide sequences that were constrained into stable water-soluble α-helices by connecting amino acid side chains to form cyclic pentapeptide components...
June 21, 2017: ACS Chemical Biology
https://www.readbyqxmd.com/read/28603971/enhanced-and-prolonged-cell-penetrating-abilities-of-arginine-rich-peptides-by-introducing-cyclic-%C3%AE-%C3%AE-disubstituted-%C3%AE-amino-acids-with-stapling
#10
Makoto Oba, Masayuki Kunitake, Takuma Kato, Atsushi Ueda, Masakazu Tanaka
Cell-penetrating peptides are receiving increasing attention as drug delivery tools, and the search for peptides with high cell-penetrating ability and negligible cytotoxicity has become a critical research topic. Herein, cyclic α,α-disubstituted α-amino acids were introduced into arginine-rich peptides and an additional staple was provided in the side chain. The peptides designed in the present study showed more enhanced and prolonged cell-penetrating abilities than an arginine nonapeptide due to high resistance to protease and conformationally stable helical structures...
July 19, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28544962/effect-of-immobilization-on-the-antimicrobial-activity-of-a-cysteine-terminated-antimicrobial-peptide-cecropin-p1-tethered-to-silica-nanoparticle-against-e-coli-o157-h7-edl933
#11
Xi Wu, Pei-Hsun Wei, Xiao Zhu, Mary J Wirth, Arun Bhunia, Ganesan Narsimhan
Antimicrobial peptides (AMPs) have the ability to penetrate the cell membrane, form pores which eventually lead to cell death. Immobilization of AMP on nanoparticles can play a major role in antimicrobial materials, biosensors for pathogen detection and in food safety. The minimum inhibitory concentration (MIC) of free Cecropin P1 (CP1, sequence SWLSTAKKLENSAKKRLSEGIAIAIQGGPR) and adsorbed on silica nanoparticle against E. coli O157:H7 EDL933 were 0.78μg/ml. This was found to be consistent with preservation of α-helical secondary structure of CP1 upon adsorption as indicated by circular dichroism (CD)...
May 17, 2017: Colloids and Surfaces. B, Biointerfaces
https://www.readbyqxmd.com/read/28528116/ph-controllable-cell-penetrating-polypeptide-that-exhibits-cancer-targeting
#12
DaeYong Lee, Ilkoo Noh, Jisang Yoo, N Sanoj Rejinold, Yeu-Chun Kim
Helical peptides were naturally-occurring ordered conformations that mediated various biological functions essential for biotechnology. However, it was difficult for natural helical polypeptides to be applied in biomedical fields due to low bioavailability. To avoid these problems, synthetic alpha-helical polypeptides have recently been introduced by further modifying pendants in the side chain. In spite of an attractive biomimetic helical motif, these systems could not be tailored for targeted delivery mainly due to nonspecific binding events...
July 15, 2017: Acta Biomaterialia
https://www.readbyqxmd.com/read/28525708/affinity-based-assembly-of-peptides-on-plasmonic-nanoparticles-delivered-intracellularly-with-light-activated-control
#13
Demosthenes P Morales, William R Wonderly, Xiao Huang, Meghan McAdams, Amanda B Chron, Norbert O Reich
We report a universal strategy for functionalizing near-infrared light-responsive nanocarriers with both a peptide "cargo" and an orthogonal cell-penetrating peptide. Modularity of both the cargo and the internalization peptide attachment is an important feature of these materials relying on the robust affinity of polyhistidine tags to nitrilotriacetic acid in the presence of nickel as well as the affinity of biotin labeled peptides to streptavidin. Attachment to the gold surface uses thiol-labeled scaffolds terminated with the affinity partner...
July 19, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28469145/investigation-of-cationicity-and-structure-of-pseudin-2-analogues-for-enhanced-bacterial-selectivity-and-anti-inflammatory-activity
#14
Dasom Jeon, Min-Cheol Jeong, Binu Jacob, Jeong Kyu Bang, Eun-Hee Kim, Chaejoon Cheong, In Duk Jung, Yoonkyung Park, Yangmee Kim
Pseudin-2 (Ps), isolated from the frog Pseudis paradoxa, exhibits potent antibacterial activity and cytotoxicity. To develop antimicrobial peptides with anti-inflammatory activity and low cytotoxicity, we designed Ps analogues with Lys substitutions, resulting in elevated amphipathic α-helical structure and cationicity. We further substituted Gly(11) with Pro (Ps-P analogues) to increase bacterial cell selectivity. Ps analogues retained antimicrobial activity and exhibited reduced cytotoxicity, whereas Ps-P analogues exhibited lower cytotoxicity and antimicrobial activity...
May 3, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28436014/a-critical-assessment-of-the-synthesis-and-biological-activity-of-p53-human-double-minute-2-stapled-peptide-inhibitors
#15
Rike Wallbrecher, Patrick Chène, Stephan Ruetz, Therese Stachyra, Thomas Vorherr, Roland Brock
BACKGROUND AND PURPOSE: Helix stapling enhances the activity of peptides that interact with a target protein in a helical conformation. These staples are also supposed to change the pharmacokinetics of the molecules and promote cytoplasmic targeting. We assessed the extent to which the pharmacokinetic characteristics are a function of the staple for a peptide inhibiting the interaction of p53 with the human double minute 2 (Hdm2) protein and differ from those of the standard cationic cell-penetrating peptide nona-arginine...
August 2017: British Journal of Pharmacology
https://www.readbyqxmd.com/read/28431354/first-example-of-peptides-targeting-the-dimer-interface-of-leishmania-infantum-trypanothione-reductase-with-potent-in%C3%A2-vitro-antileishmanial-activity
#16
Marta Ruiz-Santaquiteria, Pedro A Sánchez-Murcia, Miguel A Toro, Héctor de Lucio, Kilian Jesús Gutiérrez, Sonia de Castro, Filipa A C Carneiro, Federico Gago, Antonio Jiménez-Ruiz, María-José Camarasa, Sonsoles Velázquez
A series of 9-mer and 13-mer amide-bridged cyclic peptides derived from the linear prototype Ac-PKIIQSVGIS-Nle-K-Nle-NH2 (Toro et al. ChemBioChem2013) has been designed and synthesized by introduction of the lactam between amino acid side chains that are separated by one helical turn (i, i+4). All of these compounds were tested in vitro as both dimerization and enzyme inhibitors of Leishmania infantum trypanothione reductase (Li-TryR). Three of the 13-mer cyclic peptide derivatives (3, 4 and 6) inhibited the oxidoreductase activity of Li-TryR in the low micromolar range and they also disrupted enzyme dimerization...
July 28, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28414223/diversity-oriented-stapling-yields-intrinsically-cell-penetrant-inducers-of-autophagy
#17
Leila Peraro, Zhongju Zou, Kamlesh M Makwana, Ashleigh E Cummings, Haydn L Ball, Hongtao Yu, Yu-Shan Lin, Beth Levine, Joshua A Kritzer
Autophagy is an essential pathway by which cellular and foreign material are degraded and recycled in eukaryotic cells. Induction of autophagy is a promising approach for treating diverse human diseases, including neurodegenerative disorders and infectious diseases. Here, we report the use of a diversity-oriented stapling approach to produce autophagy-inducing peptides that are intrinsically cell-penetrant. These peptides induce autophagy at micromolar concentrations in vitro, have aggregate-clearing activity in a cellular model of Huntington's disease, and induce autophagy in vivo...
June 14, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28356384/il-26-confers-proinflammatory-properties-to-extracellular-dna
#18
Caroline Poli, Jean François Augusto, Jonathan Dauvé, Clément Adam, Laurence Preisser, Vincent Larochette, Pascale Pignon, Ariel Savina, Simon Blanchard, Jean François Subra, Alain Chevailler, Vincent Procaccio, Anne Croué, Christophe Créminon, Alain Morel, Yves Delneste, Helmut Fickenscher, Pascale Jeannin
In physiological conditions, self-DNA released by dying cells is not detected by intracellular DNA sensors. In chronic inflammatory disorders, unabated inflammation has been associated with a break in innate immune tolerance to self-DNA. However, extracellular DNA has to complex with DNA-binding molecules to gain access to intracellular DNA sensors. IL-26 is a member of the IL-10 cytokine family, overexpressed in numerous chronic inflammatory diseases, in which biological activity remains unclear. We demonstrate in this study that IL-26 binds to genomic DNA, mitochondrial DNA, and neutrophil extracellular traps, and shuttles them in the cytosol of human myeloid cells...
May 1, 2017: Journal of Immunology: Official Journal of the American Association of Immunologists
https://www.readbyqxmd.com/read/28275774/antibiotic-gold-tethering-of-antimicrobial-peptides-to-gold-nanoparticles-maintains-conformational-flexibility-of-peptides-and-improves-trypsin-susceptibility
#19
Parvesh Wadhwani, Nico Heidenreich, Benjamin Podeyn, Jochen Bürck, Anne S Ulrich
Peptide-coated nanoparticles are valuable tools for diverse biological applications, such as drug delivery, molecular recognition, and antimicrobial action. The functionalization of pre-fabricated nanoparticles with free peptides in solution is inefficient either due to aggregation of the particles or due to the poor ligand exchange reaction. Here, we present a one-pot synthesis for preparing gold nanoparticles with a homogeneous distribution that are covered in situ with cationic peptides in a site-selective manner via Cys-residue at the N-terminus...
March 9, 2017: Biomaterials Science
https://www.readbyqxmd.com/read/28249727/investigations-into-the-potential-anticancer-activity-of-maximin-h5
#20
Sarah R Dennison, Frederick Harris, David A Phoenix
Here we report the first major example of anionic amphibian host defence peptides (HDPs) with anticancer activity. Maximin H5 (MH5N) is a C-terminally amidated, anionic host defence peptide from toads of the Bombina genus, which was shown to possess activity against the glioma cell line, T98G (EC50 = 125 μM). The peptide adopted high levels of α-helical structure (57.3%) in the presence of model cancer membranes (DMPC:DMPS in a molar ratio of 10:1). MH5N also showed a strong ability to penetrate these model membranes (Π = 10...
June 2017: Biochimie
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