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Helical cell penetrating peptide

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https://www.readbyqxmd.com/read/27874065/antimicrobial-peptide-potency-is-facilitated-by-greater-conformational-flexibility-when-binding-to-gram-negative-bacterial-inner-membranes
#1
Sarah-Beth T A Amos, Louic S Vermeer, Philip M Ferguson, Justyna Kozlowska, Matthew Davy, Tam T Bui, Alex F Drake, Christian D Lorenz, A James Mason
The interaction of antimicrobial peptides (AMPs) with the inner membrane of Gram-negative bacteria is a key determinant of their abilities to exert diverse bactericidal effects. Here we present a molecular level understanding of the initial target membrane interaction for two cationic α-helical AMPs that share structural similarities but have a ten-fold difference in antibacterial potency towards Gram-negative bacteria. The binding and insertion from solution of pleurocidin or magainin 2 to membranes representing the inner membrane of Gram-negative bacteria, comprising a mixture of 128 anionic and 384 zwitterionic lipids, is monitored over 100 ns in all atom molecular dynamics simulations...
November 22, 2016: Scientific Reports
https://www.readbyqxmd.com/read/27760360/charge-distribution-fine-tunes-the-translocation-of-%C3%AE-helical-amphipathic-peptides-across-membranes
#2
Francis D O Ablan, B Logan Spaller, Kaitlyn I Abdo, Paulo F Almeida
Hundreds of cationic antimicrobial and cell-penetrating peptides (CPPs) form amphipathic α-helices when bound to lipid membranes. Here, we test two hypotheses for the differences in the ability of these peptides to translocate across membranes. The first, which we now call the hydrophobicity hypothesis, is that peptide translocation is determined by the Gibbs energy of insertion into the bilayer from the membrane interface. The second, which we call the charge-distribution hypothesis, is that translocation is determined by whether the distribution of cationic residues in the peptide can transiently stabilize a high-energy inserted intermediate by forming salt bridges to the phosphates of lipid headgroups...
October 18, 2016: Biophysical Journal
https://www.readbyqxmd.com/read/27696822/self-assembled-peptide-based-system-for-mitochondrial-targeted-gene-delivery-functional-and-structural-insights
#3
Jo-Ann Chuah, Akimasa Matsugami, Fumiaki Hayashi, Keiji Numata
Human mitochondrial dysfunction can lead to severe and often deadly diseases, for which there are no known cures. Although the targeted delivery of therapeutic gene to mitochondria is a promising approach to alleviate these disorders, gene carrier systems for the selective delivery of functional DNA into the mitochondria of living mammalian cells are currently unavailable. Here we rationally developed dual-domain peptides containing DNA-condensing/cell-penetrating/endosome-disruptive and mitochondria-targeting sequences...
October 3, 2016: Biomacromolecules
https://www.readbyqxmd.com/read/27664329/optimization-of-in-vivo-dna-delivery-with-nickfect-peptide-vectors
#4
Krista Freimann, Piret Arukuusk, Kaido Kurrikoff, Luís Daniel Ferreira Vasconcelos, Kadi-Liis Veiman, Julia Uusna, Helerin Margus, Alfonso T Garcia-Sosa, Margus Pooga, Ülo Langel
As the field of gene therapy progresses, an increasingly urgent need has arisen for efficient and non-toxic vectors for the in vivo delivery of nucleic acids. Cell-penetrating peptides (CPP) are very efficient transfection reagents in vitro, however, their application in vivo needs improvement. To enhance in vivo transfection we designed various CPPs based on previous knowledge of internalization studies and physiochemical properties of NickFect (NF) nanoparticles. We show that increment of the helicity of these Transportan10 analogues improves the transfection efficiency...
November 10, 2016: Journal of Controlled Release: Official Journal of the Controlled Release Society
https://www.readbyqxmd.com/read/27609319/development-of-a-cell-penetrating-peptide-that-exhibits-responsive-changes-in-its-secondary-structure-in-the-cellular-environment
#5
Hiroko Yamashita, Takuma Kato, Makoto Oba, Takashi Misawa, Takayuki Hattori, Nobumichi Ohoka, Masakazu Tanaka, Mikihiko Naito, Masaaki Kurihara, Yosuke Demizu
Cell-penetrating peptides (CPP) are received a lot of attention as an intracellular delivery tool for hydrophilic molecules such as drugs, proteins, and DNAs. We designed and synthesized nona-arginine analogues 1-5 [FAM-β-Ala-(l-Arg-l-Arg-l-Pro)3-(Gly)3-NH2 (1), FAM-β-Ala-(l-Arg-l-Arg-l-Pro(NH2))3-(Gly)3-NH2 (2), FAM-β-Ala-(l-Arg-l-Arg-l-Pro(Gu))3-(Gly)3-NH2 (3), FAM-β-Ala-(l-Arg)2-(l-Pro(Gu))2-(l-Arg)4-l-Pro(Gu)-(Gly)3-NH2 (4), and FAM-β-Ala-(l-Arg)6-(l-Pro(Gu))3-(Gly)3-NH2 (5)] containing l-proline (l-Pro) or cationic proline derivatives (l-Pro(NH2) and l-Pro(Gu)), and investigated their cell-penetrating abilities...
2016: Scientific Reports
https://www.readbyqxmd.com/read/27603918/thermoresponsive-collagen-cell-penetrating-hybrid-peptide-as-nanocarrier-in-targeting-free-cell-selection-and-uptake
#6
Myungeun Oh, Chloe Hu, Selina F Urfano, Merlyn Arostegui, Katarzyna Slowinska
The effective delivery of therapeutics and imaging agents to a selected group of cells has been at the forefront of biomedical research. Unfortunately, the identification of the unique cell surface targets for cell selection remains a major challenge, particularly if cells within the selected group are not identical. Here we demonstrate a novel approach to cell section relying on a thermoresponsive peptide-based nanocarrier. The hybrid peptide containing cell-penetrating peptide (CPP) and collagen (COLL) domains is designed to undergo coil-to-helix transition (folding) below physiological temperature...
October 4, 2016: Analytical Chemistry
https://www.readbyqxmd.com/read/27595096/membrane-thinning-and-thickening-induced-by-membrane-active-amphipathic-peptides
#7
Stephan L Grage, Sergii Afonin, Sezgin Kara, Gernot Buth, Anne S Ulrich
Membrane thinning has been discussed as a fundamental mechanism by which antimicrobial peptides can perturb cellular membranes. To understand which factors play a role in this process, we compared several amphipathic peptides with different structures, sizes and functions in their influence on the lipid bilayer thickness. PGLa and magainin 2 from X. laevis were studied as typical representatives of antimicrobial cationic amphipathic α-helices. A 1:1 mixture of these peptides, which is known to possess synergistically enhanced activity, allowed us to evaluate whether and how this synergistic interaction correlates with changes in membrane thickness...
2016: Frontiers in Cell and Developmental Biology
https://www.readbyqxmd.com/read/27442521/nonhemolytic-cell-penetrating-peptides-site-specific-introduction-of-glutamine-and-lysine-residues-into-the-%C3%AE-helical-peptide-causes-deletion-of-its-direct-membrane-disrupting-ability-but-retention-of-its-cell-penetrating-ability
#8
Seoyeon Kim, Soonsil Hyun, Yuri Lee, Yan Lee, Jaehoon Yu
Cell-penetrating peptides (CPPs) often have cationic and amphipathic characteristics that are commonly associated with α-helical peptides. These features give CPPs both membrane demolishing and penetrating abilities. To make CPPs safe for biomedical applications, their toxicities resulting from their membrane demolishing abilities must be removed while their cell penetrating abilities must be retained. In this study, we systematically constructed mutants of the amphipathic α-helical model peptide (LKKLLKLLKKLLKLAG, LK peptide)...
September 12, 2016: Biomacromolecules
https://www.readbyqxmd.com/read/27391304/membrane-mediated-antimicrobial-and-antitumor-activity-of-cathelicidin-6-structural-insights-from-molecular-dynamics-simulation-on-multi-microsecond-scale
#9
Bikash Ranjan Sahoo, Toshimichi Fujiwara
The cathelicidin derived bovine antimicrobial peptide BMAP27 exhibits an effective microbicidal activity and moderate cytotoxicity towards erythrocytes. Irrespective of its therapeutic and multidimensional potentiality, the structural studies are still elusive. Moreover, the mechanism of BMAP27 mediated pore formation in heterogeneous lipid membrane systems is poorly explored. Here, we studied the effect of BMAP27 in model cell-membrane systems such as zwitterionic, anionic, thymocytes-like (TLM) and leukemia-like membranes (LLM) by performing molecular dynamics (MD) simulation longer than 100 μs...
2016: PloS One
https://www.readbyqxmd.com/read/27320388/non-enveloped-virus-entry-structural-determinants-and-mechanism-of-functioning-of-a-viral-lytic-peptide
#10
Saumya Bajaj, Debajit Dey, Rohan Bhukar, Mohit Kumar, Manidipa Banerjee
In the absence of lipid envelopes and associated fusion proteins, non-enveloped viruses employ membrane lytic peptides to breach the limiting membranes of host cells. Although several of these lytic peptides have been identified and characterized, their manner of deployment and interaction with host membranes remains unclear in most cases. We are using the gamma peptide of Flock House Virus (FHV), a model non-enveloped virus, to understand the mechanistic details of non-enveloped virus interaction with host cell membranes...
August 28, 2016: Journal of Molecular Biology
https://www.readbyqxmd.com/read/27271216/design-of-an-%C3%AE-helical-antimicrobial-peptide-with-improved-cell-selective-and-potent-anti-biofilm-activity
#11
Shi-Kun Zhang, Jin-Wen Song, Feng Gong, Su-Bo Li, Hong-Yu Chang, Hui-Min Xie, Hong-Wei Gao, Ying-Xia Tan, Shou-Ping Ji
AR-23 is a melittin-related peptide with 23 residues. Like melittin, its high α-helical amphipathic structure results in strong bactericidal activity and cytotoxicity. In this study, a series of AR-23 analogues with low amphipathicity were designed by substitution of Ala1, Ala8 and Ile17 with positively charged residues (Arg or Lys) to study the effect of positively charged residue distribution on the biological viability of the antimicrobial peptide. Substitution of Ile17 on the nonpolar face with positively charged Lys dramatically altered the hydrophobicity, amphipathicity, helicity and the membrane-penetrating activity against human cells as well as the haemolytic activity of the peptide...
2016: Scientific Reports
https://www.readbyqxmd.com/read/27237727/sap-e-a-cell-penetrating-polyproline-helix-at-lipid-interfaces
#12
Johannes Franz, Marco Lelle, Kalina Peneva, Mischa Bonn, Tobias Weidner
Cell-penetrating peptides (CPPs) are short membrane-permeating amino acid sequences that can be used to deliver cargoes, e.g. drugs, into cells. The mechanism for CPP internalization is still subject of ongoing research. An interesting family of CPPs is the sweet arrow peptides - SAP(E) - which are known to adopt a polyproline II helical secondary structure. SAP(E) peptides stand out among CPPs because they carry a net negative charge while most CPPs are positively charged, the latter being conducive to electrostatic interaction with generally negatively charged membranes...
September 2016: Biochimica et Biophysica Acta
https://www.readbyqxmd.com/read/27195657/amphipathicity-determines-different-cytotoxic-mechanisms-of-lysine-or-arginine-rich-cationic-hydrophobic-peptides-in-cancer-cells
#13
Xiaoli Liu, Rui Cao, Sha Wang, Junli Jia, Hao Fei
Cationic amphipathic peptides (CAPs) are known to be able to cause membrane destabilization and induce cell death, yet how the hydrophobicity, amphipathicity, and lysine (K)/arginine (R) composition synergistically affect the peptide activity remains incompletely understood. Here, we designed a panel of peptides based on the well-known anticancer peptide KLA. Increasing hydrophobicity enhanced the cytotoxicities of both the K- and R-rich peptides. Peptides with an intact amphipathic helical interface can cause instant cell death through a membrane lysis mechanism...
June 9, 2016: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/27001828/characterization-of-the-complex-formed-by-%C3%AE-glucocerebrosidase-and-the-lysosomal-integral-membrane-protein-type-2
#14
Friederike Zunke, Lisa Andresen, Sophia Wesseler, Johann Groth, Philipp Arnold, Michelle Rothaug, Joseph R Mazzulli, Dimitri Krainc, Judith Blanz, Paul Saftig, Michael Schwake
The lysosomal integral membrane protein type-2 (LIMP-2) plays a pivotal role in the delivery of β-glucocerebrosidase (GC) to lysosomes. Mutations in GC result in Gaucher's disease (GD) and are the major genetic risk factor for the development of Parkinson's disease (PD). Variants in the LIMP-2 gene cause action myoclonus-renal failure syndrome and also have been linked to PD. Given the importance of GC and LIMP-2 in disease pathogenesis, we studied their interaction sites in more detail. Our previous data demonstrated that the crystal structure of LIMP-2 displays a hydrophobic three-helix bundle composed of helices 4, 5, and 7, of which helix 5 and 7 are important for ligand binding...
April 5, 2016: Proceedings of the National Academy of Sciences of the United States of America
https://www.readbyqxmd.com/read/26987762/critical-evaluation-and-compilation-of-physicochemical-determinants-and-membrane-interactions-of-mmgp1-antifungal-peptide
#15
Muthuirulan Pushpanathan, Sharma Pooja, Paramasamy Gunasekaran, Jeyaprakash Rajendhran
A growing issue of pathogen resistance to antibiotics has fostered the development of innovative approaches for novel drug development. Here, we report the physicochemical and biological properties of an antifungal peptide, MMGP1, based on computational analysis. Computation of physicochemical properties has revealed that the natural biological activities of MMGP1 are coordinated by its intrinsic properties such as net positive charge (+5.04), amphipathicity, high hydrophobicity, low hydrophobic moment, and higher isoelectric point (11...
May 2, 2016: Molecular Pharmaceutics
https://www.readbyqxmd.com/read/26887358/mechanism-of-inhibition-of-human-islet-amyloid-polypeptide-induced-membrane-damage-by-a-small-organic-fluorogen
#16
Xiaoxu Li, Mingwei Wan, Lianghui Gao, Weihai Fang
Human islet amyloid polypeptide (hIAPP) is believed to be responsible for the death of insulin-producing β-cells. However, the mechanism of membrane damage at the molecular level has not been fully elucidated. In this article, we employ coarse- grained dissipative particle dynamics simulations to study the interactions between a lipid bilayer membrane composed of 70% zwitterionic lipids and 30% anionic lipids and hIAPPs with α-helical structures. We demonstrated that the key factor controlling pore formation is the combination of peptide charge-induced electroporation and peptide hydrophobicity-induced lipid disordering and membrane thinning...
2016: Scientific Reports
https://www.readbyqxmd.com/read/26884389/in-situ-investigation-of-peptide-lipid-interaction-between-pap248-286-and-model-cell-membranes
#17
Khoi Tan Nguyen
Sum frequency generation vibrational spectroscopy (SFG) was utilized to investigate the interaction between PAP248-286 and the two lipid bilayer systems. The present study also provides spectroscopic evidence to confirm that, although PAP248-286 is unable to penetrate into the hydrophobic core of the lipid bilayers, it is capable of interacting more intimately with the fluid-phase POPG/POPC than with the gel-phase DPPG/DPPC lipid bilayer. The helical structure content of lipid-bound PAP248-286 was also observed to be high, in contrast to the results previously reported using nuclear magnetic resonance (NMR)...
June 2016: Journal of Membrane Biology
https://www.readbyqxmd.com/read/26725435/cellular-uptake-of-igg-using-collagen-like-cell-penetrating-peptides
#18
Ryo Masuda, Kazuhiro Yamamoto, Takaki Koide
Cell-penetrating peptides (CPPs) are attractive tools for delivering macromolecules that have poor membrane permeability, such as antibodies, into cells. However, the major drawback of conventional CPPs is their instability in bodily fluids. We previously reported a novel CPP employing a collagen-like triple-helical structure that exhibited remarkable resistance against serum proteases. Herein, we report the delivery of full-length immunoglobulin G (IgG) antibody into cells using a triple-helical CPP. The CPP was conjugated to IgG via a one-pot reaction using 2-iminothiolane as a crosslinking reagent...
2016: Biological & Pharmaceutical Bulletin
https://www.readbyqxmd.com/read/26623479/intracellular-target-specific-accretion-of-cell-penetrating-peptides-and-bioportides-ultrastructural-and-biological-correlates
#19
Sarah Jones, Julia Uusna, Ülo Langel, John Howl
Cell penetrating peptide (CPP) technologies provide a viable strategy to regulate the activities of intracellular proteins that may be intractable to other biological agents. In particular, the cationic helical domains of proteins have proven to be a reliable source of proteomimetic bioportides, CPPs that modulate the activities of intracellular proteins. In this study we have employed live cell imaging confocal microscopy to determine the precise intracellular distribution of a chemically diverse set of CPPs and bioportides...
January 20, 2016: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/26560998/a-helix-stabilized-cell-penetrating-peptide-as-an-intracellular-delivery-tool
#20
Hiroko Yamashita, Makoto Oba, Takashi Misawa, Masakazu Tanaka, Takayuki Hattori, Mikihiko Naito, Masaaki Kurihara, Yosuke Demizu
Two types of cationic cyclic α,α-disubstituted α-amino acids: ApiC2NH2 (which possesses a lysine mimic side chain) and Api(C2Gu) (which possesses an arginine mimic side chain), were developed. These amino acids were incorporated into an arginine-based peptide sequence [(L-Arg-L-Arg-dAA)3: dAA=ApiC2NH2 or Api(C2Gu)], and the relationship between the secondary structures of the resulting peptides and their ability to pass through cell membranes was investigated. The peptide containing Api(C2Gu) formed a stable α-helical structure and was more effective at penetrating cells than the nonhelical Arg nonapeptide (R9)...
January 2016: Chembiochem: a European Journal of Chemical Biology
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