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Helical cell penetrating peptide

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https://www.readbyqxmd.com/read/29353482/monitoring-the-orientational-changes-of-alamethicin-incorporating-into-bilayer-lipid-membranes
#1
Enrico Forbrig, Jana K Staffa, Johannes Salewski, Maria Andrea Mroginski, Peter Hildebrandt, Jacek Kozuch
Antimicrobial peptides (AMPs) are the first line of defense after contact of an infectious invader, e.g. bacterium or virus, with a host and an integral part of the innate immune system of humans. Their broad spectrum of biological functions ranges from cell membrane disruption over facilitation of chemotaxis to interaction with membrane-bound or intracellu-lar receptors, thus providing novel strategies to overcome bacterial resistances. Especially, the clarification of the mecha-nisms and dynamics of AMP incorporation into bacterial membranes is of high interest and different mechanistic models are still under discussion...
January 20, 2018: Langmuir: the ACS Journal of Surfaces and Colloids
https://www.readbyqxmd.com/read/29339518/iterative-optimization-yields-mcl-1-targeting-stapled-peptides-with-selective-cytotoxicity-to-mcl-1-dependent-cancer-cells
#2
Raheleh Rezaei Araghi, Gregory H Bird, Jeremy A Ryan, Justin M Jenson, Marina Godes, Jonathan R Pritz, Robert A Grant, Anthony Letai, Loren D Walensky, Amy E Keating
Bcl-2 family proteins regulate apoptosis, and aberrant interactions of overexpressed antiapoptotic family members such as Mcl-1 promote cell transformation, cancer survival, and resistance to chemotherapy. Discovering potent and selective Mcl-1 inhibitors that can relieve apoptotic blockades is thus a high priority for cancer research. An attractive strategy for disabling Mcl-1 involves using designer peptides to competitively engage its binding groove, mimicking the structural mechanism of action of native sensitizer BH3-only proteins...
January 16, 2018: Proceedings of the National Academy of Sciences of the United States of America
https://www.readbyqxmd.com/read/29337270/the-cationic-tetradecapeptide-mastoparan-as-a-privileged-structure-for-drug-discovery-enhanced-antimicrobial-properties-of-mitoparan-analogues-modified-at-position-14
#3
John Howl, Lewis Howl, Sarah Jones
Mastoparan (MP) peptides, distributed in insect venoms, induce a local inflammatory response post envenomation. Most endogenous MPs share common structural elements within a tetradecapeptide sequence that adopts an amphipathic helix whilst traversing biological membranes and when bound to an intracellular protein target. Rational modifications to increase cationic charge density and amphipathic helicity engineered mitoparan (MitP), a mitochondriotoxic bioportide and potent secretagogue. Following intracellular translocation, MitP is accreted by mitochondria thus indicating additional utility as an antimicrobial agent...
January 11, 2018: Peptides
https://www.readbyqxmd.com/read/29317198/rhodomyrtone-rom-is-a-membrane-active-compound
#4
Jongkon Saising, Minh Thu Nguyen, Thomas Härtner, Patrick Ebner, Abdulla Al Mamun Bhuyan, Anne Berscheid, Melanie Muehlenkamp, Sina Schäkermann, Nimerta Kumari, Martin E Maier, Supayang P Voravuthikunchai, Julia Bandow, Florian Lang, Heike Brötz-Oesterhelt, Friedrich Götz
Particularly in Asia medicinal plants with antimicrobial activity are used for therapeutic purpose. One such plant-derived antibiotic is rhodomyrtone (Rom) isolated from Rhodomyrtus tomentosa leaves. Rom shows high antibacterial activity against a wide range of Gram-positive bacteria, however, its mode of action is still unclear. Reporter gene assays and proteomic profiling experiments in Bacillus subtilis indicate that Rom does not address classical antibiotic targets like translation, transcription or DNA replication, but acts at the cytoplasmic membrane...
January 6, 2018: Biochimica et Biophysica Acta
https://www.readbyqxmd.com/read/29247564/secondary-structure-of-cell-penetrating-peptides-during-interaction-with-fungal-cells
#5
Zifan Gong, Svetlana P Ikonomova, Amy J Karlsson
Cell-penetrating peptides (CPPs) are peptides that cross cell membranes, either alone or while carrying molecular cargo. Although their interactions with mammalian cells have been widely studied, much less is known about their interactions with fungal cells, particularly at the biophysical level. We analyzed the interactions of seven CPPs (penetratin, Pep-1, MPG, pVEC, TP-10, MAP, and cecropin B) with the fungal pathogen Candida albicans using experiments and molecular simulations. Circular dichroism (CD) of the peptides revealed a structural transition from a random coil or weak helix to an α-helix occurs for all peptides when the solvent is changed from aqueous to hydrophobic...
December 16, 2017: Protein Science: a Publication of the Protein Society
https://www.readbyqxmd.com/read/29214239/protonation-enhances-the-inherent-helix-forming-propensity-of-phlip
#6
Chitrak Gupta, Blake Mertz
Cell-penetrating peptides (CPPs) can be potentially used in targeted delivery of therapeutic cargoes. However, their conformation in solution is poorly understood. We employed molecular dynamics simulations to probe the structural fluctuations of an anionic CPP, pH Low Insertion Peptide (pHLIP), in solution to determine the effects of modifications to selected residues on the structure of pHLIP. Two types of modifications were tested: (1) protonation of aspartic acid residues and (2) point mutations known to affect the acid sensitivity of pHLIP...
November 30, 2017: ACS Omega
https://www.readbyqxmd.com/read/29090725/arginine-modification-of-lycosin-i-to-improve-inhibitory-activity-against-cancer-cells
#7
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
#8
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
#9
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
#10
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
#11
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
#12
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
#13
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
#14
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
#15
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
#16
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
#17
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
#18
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
#19
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
#20
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
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