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Helical cell penetrating peptide

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https://www.readbyqxmd.com/read/28275774/antibiotic-gold-tethering-of-antimicrobial-peptides-to-gold-nanoparticles-maintains-conformational-flexibility-of-peptides-and-improves-trypsin-susceptibility
#1
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/maximin-h5-is-an-anticancer-peptide
#2
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 is a C-terminally amidated, anionic host defence peptide (MH5N) 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...
February 26, 2017: Biochimie
https://www.readbyqxmd.com/read/28236573/modifying-antigen-encapsulating-liposomes-with-kala-facilitates-mhc-class-i-antigen-presentation-and-enhances-anti-tumor-effects
#3
Naoya Miura, Hidetaka Akita, Naho Tateshita, Takashi Nakamura, Hideyoshi Harashima
For a successful anti-cancer vaccine, antigen presentation on the major histocompatibility complex (MHC) class I is a requirement. To accomplish this, an antigen must be delivered to the cytoplasm by overcoming the endosome/lysosome. We previously reported that a lipid nanoparticle modified with a KALA peptide (WEAKLAKALAKALAKHLAKALAKALKA), an α-helical cationic peptide, permits the encapsulated pDNA to be efficiently delivered to the cytoplasm in bone marrow-derived dendritic cells (BMDCs). Herein, we report on the use of KALA-modified liposomes as an antigen carrier, in an attempt to induce potent antigen-specific cellular immunity...
February 21, 2017: Molecular Therapy: the Journal of the American Society of Gene Therapy
https://www.readbyqxmd.com/read/28212487/interactions-between-membranes-and-metaphilic-polypeptide-architectures-with-diverse-sidechain-populations
#4
Michelle W Lee, Ming Han, Guilherme Volpe Bossa, Carly Snell, Ziyuan Song, Haoyu Tang, Lichen Yin, Jianjun Cheng, Sylvio May, Erik Luijten, Gerard C L Wong
At physiological conditions, most proteins or peptides can fold into relatively stable structures that present on their molecular surfaces specific chemical patterns partially smeared out by thermal fluctuations. These nanoscopically defined patterns of charge, hydrogen bonding, and/or hydrophobicity, along with their elasticity and shape stability (folded proteins have Young's moduli of ~1 × 10(8) Pa), largely determine and limit the interactions of these molecules, such as molecular recognition and allosteric regulation...
February 17, 2017: ACS Nano
https://www.readbyqxmd.com/read/28190655/development-of-helix-stabilized-cell-penetrating-peptides-containing-cationic-%C3%AE-%C3%AE-disubstituted-amino-acids-as-helical-promoters
#5
Hiroko Yamashita, Takashi Misawa, Makoto Oba, Masakazu Tanaka, Mikihiko Naito, Masaaki Kurihara, Yosuke Demizu
Cell-penetrating peptides (CPP) have attracted many scientists' attention as intracellular delivery tools due to their high cargo molecule transportation efficiency and low cytotoxicity. Therefore, in many research fields CPP, such as HIV-Tat and oligoarginine (Rn), are used to deliver hydrophilic drugs and biomolecules, including proteins, DNA, and RNA. We designed four types of CPP that contained cationic α,α-disubstituted amino acids (Api(C2Gu) and Api(C4Gu)) as helical promoters; i.e., 1-4 [FAM-β-Ala-(l-Arg-l-Arg-Xaa)3-(Gly)3-NH2 (1: Xaa=Api(C2Gu), 2: Xaa=Api(C4Gu)), 3: FAM-β-Ala-(l-Arg)8-Api(C2Gu)-(Gly)3-NH2, and 4: FAM-β-Ala-(l-Arg)5-Api(C2Gu)-(l-Arg)2-Api(C2Gu)-(Gly)3-NH2], and investigated their preferred secondary structures and cell membrane-penetrating ability...
February 1, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28105269/electrophilic-helical-peptides-that-bond-covalently-irreversibly-and-selectively-in-a-protein-protein-interaction-site
#6
Aline Dantas de Araujo, Junxian Lim, Andrew C Good, Renato T Skerlj, David P Fairlie
Protein-protein interactions mediate most physiological and disease processes. Helix-constrained peptides potently mimic or inhibit these interactions by making multiple contacts over large surface areas. However, despite high affinities, they typically have short lifetimes bound to the protein. Here we insert both a helix-inducing constraint and an adjacent electrophile into the native peptide ligand BIM to target the oncogenic protein Bcl2A1. The modified BIM peptide bonds covalently and irreversibly to one cysteine within the helix-binding groove of Bcl2A1, but not to two other exposed cysteines on its surface, and shows no covalent bonding to other Bcl2 proteins...
January 12, 2017: ACS Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28093876/development-of-poly-lactide-co-glycolide-nanoparticles-functionalized-with-a-mitochondria-penetrating-peptide
#7
Francesca Selmin, Giulia Magri, Chiara G M Gennari, Silvia Marchianò, Nicola Ferri, Sara Pellegrino
The development of mitochondria-targeting cell permeable vectors represents a promising therapeutic approach for several diseases, such as cancer and oxidative pathologies. Nevertheless, access to mitochondria can be difficult. A new hybrid material composed by poly(lactide-co-glycolide) (PLGA) functionalized with a 6-mer mitochondria penetrating peptide (MPP), consisting in alternating arginine and unnatural cyclohexylalanine, was developed. Circular dichroism, FT-IR and DSC studies indicated that the conjugation of the peptide with the polymer led to the obtainment of a more rigid material with respect to both PLGA and MPP as such...
February 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28013149/how-charge-distribution-influences-the-function-of-membrane-active-peptides-lytic-or-cell-penetrating
#8
Long Chen, Qiang Zhang, Xiushuang Yuan, Yimeng Cao, Yanyan Yuan, Huiwei Yin, Xiufang Ding, Zhentai Zhu, Shi-Zhong Luo
Lytic and cell-penetrating peptides (CPPs) are both membrane-active peptides sharing similar physicochemical properties. Although their respective functions have been intensively investigated, the difference of intrinsic properties between these two types of peptides is rarely discussed. In this study, we designed a series of analogs of a recently discovered CPP ZXR-1 (FKIGGFIKKLWRSKLA) by varying the charge distributions both on the helical wheel projection and along the sequence. These peptides showed different functions on cell membranes, including membrane lytic (peptide Z1), cell-penetrating (peptide ZXR-1, Z2 and Z3), and inactive (peptide Z4) peptides...
December 21, 2016: International Journal of Biochemistry & Cell Biology
https://www.readbyqxmd.com/read/27924991/improving-cell-penetration-of-helical-peptides-stabilized-by-n-terminal-crosslinked-aspartic-acids
#9
Hui Zhao, Yanhong Jiang, Yuan Tian, Dan Yang, Xuan Qin, Zigang Li
Cell penetration and nucleus translocation efficiency are important for the cellular activities of peptide therapeutics. For helical peptides stabilized by N-terminal crosslinked aspartic acid, correlations between their penetration efficiency/nucleus translocation and physicochemical properties were studied. An increase in hydrophobicity and isoelectric point will promote cellular uptake and nucleus translocation of stabilized helices.
December 7, 2016: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/27916828/enhancing-anticancer-effect-of-gefitinib-across-the-blood-brain-barrier-model-using-liposomes-modified-with-one-%C3%AE-helical-cell-penetrating-peptide-or-glutathione-and-tween-80
#10
Kuan-Hung Lin, Shu-Ting Hong, Hsiang-Tsui Wang, Yu-Li Lo, Anya Maan-Yuh Lin, James Chih-Hsin Yang
Epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors (TKI), such as gefitinib, have been demonstrated to effectively treat the patients of extracranial non-small cell lung cancer (NSCLC). However, these patients often develop brain metastasis (BM) during their disease course. The major obstacle to treat BM is the limited penetration of anticancer drugs across the blood-brain barrier (BBB). In the present study, we utilized gefitinib-loaded liposomes with different modifications to improve gefitinib delivery across the in vitro BBB model of bEnd...
November 29, 2016: International Journal of Molecular Sciences
https://www.readbyqxmd.com/read/27874065/antimicrobial-peptide-potency-is-facilitated-by-greater-conformational-flexibility-when-binding-to-gram-negative-bacterial-inner-membranes
#11
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
#12
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
#13
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...
November 14, 2016: Biomacromolecules
https://www.readbyqxmd.com/read/27664329/optimization-of-in-vivo-dna-delivery-with-nickfect-peptide-vectors
#14
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
#15
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
#16
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
#17
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
#18
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
#19
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
#20
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
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