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Yurii Moroz, W. Binder, P. Nygren, Gregory Caputo, I. Korendovych (2013)
Painting proteins blue: β-(1-azulenyl)-L-alanine as a probe for studying protein-protein interactions.Chemical communications, 49 5
Kook-Han Kim, Dong-Kyun Ko, Yong-Tae Kim, Nam Kim, J. Paul, Shao-Qing Zhang, C. Murray, Rudresh Acharya, W. DeGrado, Yong Kim, G. Grigoryan (2016)
Protein-directed self-assembly of a fullerene crystalNature Communications, 7
(2009)
Helical Wheel Projections, Id: wheel.pl,v
Bashkim Kokona, Andrew Kim, R. Roden, J. Daniels, Brian Pepe-Mooney, Brian Kovaric, J. Paula, K. Johnson, R. Fairman (2009)
Self assembly of coiled-coil peptide-porphyrin complexes.Biomacromolecules, 10 6
(2018)
Antimicrobial activity of a porphyrin binding peptide
Victor Villapun, L. Dover, A. Cross, S. González (2016)
Antibacterial Metallic Touch SurfacesMaterials, 9
Gregory Caputo, E. London (2013)
Analyzing transmembrane protein and hydrophobic helix topography by dual fluorescence quenching.Methods in molecular biology, 974
T. Doll, R. Dey, P. Burkhard (2015)
Design and optimization of peptide nanoparticlesJournal of Nanobiotechnology, 13
Gregory Caputo, E. London (2003)
Cumulative effects of amino acid substitutions and hydrophobic mismatch upon the transmembrane stability and conformation of hydrophobic alpha-helices.Biochemistry, 42 11
I. Zelezetsky, A. Tossi (2006)
Alpha-helical antimicrobial peptides--using a sequence template to guide structure-activity relationship studies.Biochimica et biophysica acta, 1758 9
R. Young, J. Gill (2015)
Phage therapy redux—What is to be done?Science, 350
K. Kuroda, Gregory Caputo, W. DeGrado (2009)
The role of hydrophobicity in the antimicrobial and hemolytic activities of polymethacrylate derivatives.Chemistry, 15 5
Rae Snyder, Susan Butch, A. Reig, W. DeGrado, E. Solomon (2015)
Molecular-Level Insight into the Differential Oxidase and Oxygenase Reactivities of de Novo Due Ferri Proteins.Journal of the American Chemical Society, 137 29
R. Hancock, Evan Haney, Erin Gill (2016)
The immunology of host defence peptides: beyond antimicrobial activityNature Reviews Immunology, 16
Edmund Palermo, Dong-kuk Lee, A. Ramamoorthy, K. Kuroda (2011)
Role of cationic group structure in membrane binding and disruption by amphiphilic copolymers.The journal of physical chemistry. B, 115 2
Karin Öjemalm, T. Higuchi, P. Lara, E. Lindahl, H. Suga, G. Heijne (2016)
Energetics of side-chain snorkeling in transmembrane helices probed by nonproteinogenic amino acidsProceedings of the National Academy of Sciences, 113
D. Eisenberg, Erich Schwarz, M. Komaromy, R. Wall (1984)
Analysis of membrane and surface protein sequences with the hydrophobic moment plot.Journal of molecular biology, 179 1
D. Kuciauskas, Gregory Caputo (2009)
Self-assembly of peptide-porphyrin complexes leads to pH-dependent excitonic coupling.The journal of physical chemistry. B, 113 43
S. White, G. Heijne (2008)
How translocons select transmembrane helices.Annual review of biophysics, 37
A. Chamberlain, Yohan Lee, Sanguk Kim, J. Bowie (2004)
Snorkeling preferences foster an amino acid composition bias in transmembrane helices.Journal of molecular biology, 339 2
(2017)
Organization, Antibacterial Agents in Clinical Development: An Analysis of the Antibacterial Clinical Development Pipeline, Including Tuberculosis, Geneva
L. Burman, K. Nordström, H. Boman (1968)
Resistance of Escherichia coli to Penicillins V. Physiological Comparison of Two Isogenic Strains, One with Chromosomally and One with Episomally Mediated Ampicillin ResistanceJournal of Bacteriology, 96
A. Polyansky, A. Chugunov, A. Vassilevski, E. Grishin, R. Efremov (2012)
Recent advances in computational modeling of α-helical membrane-active peptides.Current protein & peptide science, 13 7
(2013)
Prevention, Antibiotic Resistance Threats in the United States 2013
Gerard Wright (2014)
Something old, something new: revisiting natural products in antibiotic drug discovery.Canadian journal of microbiology, 60 3
Gregory Caputo, E. London (2003)
Using a novel dual fluorescence quenching assay for measurement of tryptophan depth within lipid bilayers to determine hydrophobic alpha-helix locations within membranes.Biochemistry, 42 11
A. Senes, Deborah Chadi, Peter Law, Robin Walters, Vikas Nanda, W. DeGrado (2007)
E(z), a depth-dependent potential for assessing the energies of insertion of amino acid side-chains into membranes: derivation and applications to determining the orientation of transmembrane and interfacial helices.Journal of molecular biology, 366 2
(2017)
Probiotics Antimicrob Proteins 2017
J. Collier, T. Segura (2011)
Evolving the use of peptides as components of biomaterials.Biomaterials, 32 18
J. Kyte, R. Doolittle (1982)
A simple method for displaying the hydropathic character of a protein.Journal of molecular biology, 157 1
M. Gebhardt, Leonhard Henkes, S. Tayefeh, Brigitte Hertel, T. Greiner, J. Etten, D. Baumeister, Cristian Cosentino, A. Moroni, S. Kast, G. Thiel (2012)
Relevance of lysine snorkeling in the outer transmembrane domain of small viral potassium ion channels.Biochemistry, 51 28
Sarah Goderecci, E. Kaiser, Michael Yanakas, Zach Norris, Jeffrey Scaturro, Robert Oszust, Clarence Medina, Fallon Waechter, Min Heon, R. Krchnavek, Lei Yu, S. Lofland, Renée Demarest, Gregory Caputo, J. Hettinger (2017)
Silver Oxide Coatings with High Silver-Ion Elution Rates and Characterization of Bactericidal ActivityMolecules : A Journal of Synthetic Chemistry and Natural Product Chemistry, 22
P. Moja (2017)
Antibacterial agents in clinical development: an analysis of the antibacterial clinical development pipeline, including tuberculosis
F. Würthner, T. Kaiser, C. Saha-Möller (2011)
J-aggregates: from serendipitous discovery to supramolecular engineering of functional dye materials.Angewandte Chemie, 50 15
Dong-kuk Lee, A. Bhunia, S. Kotler, A. Ramamoorthy (2015)
Detergent-type membrane fragmentation by MSI-78, MSI-367, MSI-594, and MSI-843 antimicrobial peptides and inhibition by cholesterol: a solid-state nuclear magnetic resonance study.Biochemistry, 54 10
M. Branco, D. Sigano, J. Schneider (2011)
Materials from peptide assembly: towards the treatment of cancer and transmittable diseaseCurrent Opinion in Chemical Biology, 15
Zachary Ridgway, Angela Picciano, P. Gosavi, Yurii Moroz, C. Angevine, Amy Chavis, J. Reiner, I. Korendovych, Gregory Caputo (2015)
Functional characterization of a melittin analog containing a non‐natural tryptophan analogPeptide Science, 104
Haruko Takahashi, Gregory Caputo, Satyavani Vemparala, K. Kuroda (2017)
Synthetic Random Copolymers as a Molecular Platform To Mimic Host-Defense Antimicrobial Peptides.Bioconjugate chemistry, 28 5
Damian Neubauer, Maciej Jaśkiewicz, Dorian Migoń, Marta Bauer, K. Sikora, E. Sikorska, E. Kamysz, W. Kamysz (2017)
Retro analog concept: comparative study on physico-chemical and biological properties of selected antimicrobial peptidesAmino Acids, 49
D. Kuciauskas, J. Kiškis, Gregory Caputo, V. Gulbinas (2010)
Exciton annihilation and energy transfer in self-assembled peptide-porphyrin complexes depends on peptide secondary structure.The journal of physical chemistry. B, 114 48
A. Iwahori, Y. Hirota, R. Sampe, S. Miyano, N. Numao (1997)
Synthesis of reversed magainin 2 analogs enhanced antibacterial activity.Biological & pharmaceutical bulletin, 20 3
Jianguo Li, Jun-Jie Koh, Shouping Liu, R. Lakshminarayanan, C. Verma, R. Beuerman (2017)
Membrane Active Antimicrobial Peptides: Translating Mechanistic Insights to DesignFrontiers in Neuroscience, 11
Gregory Caputo, E. London (2004)
Position and ionization state of Asp in the core of membrane-inserted alpha helices control both the equilibrium between transmembrane and nontransmembrane helix topography and transmembrane helix positioning.Biochemistry, 43 27
H. Fry, A. Lehmann, J. Saven, W. DeGrado, M. Therien (2010)
Computational design and elaboration of a de novo heterotetrameric alpha-helical protein that selectively binds an emissive abiological (porphinato)zinc chromophore.Journal of the American Chemical Society, 132 11
Jeongjoon Choi, E. Groisman (2016)
Acidic pH sensing in the bacterial cytoplasm is required for Salmonella virulenceMolecular Microbiology, 101
Seoyeon Kim, Soonsil Hyun, Yuri Lee, Yan Lee, Jaehoon Yu (2016)
Nonhemolytic Cell-Penetrating Peptides: Site Specific Introduction of Glutamine and Lysine Residues into the α-Helical Peptide Causes Deletion of Its Direct Membrane Disrupting Ability but Retention of Its Cell Penetrating Ability.Biomacromolecules, 17 9
A. Reig, M. Pires, Rae Snyder, Yibing Wu, Hyunil Jo, Daniel Kulp, Susan Butch, Jennifer Calhoun, T. Szyperski, E. Solomon, W. DeGrado (2012)
Erratum: Alteration of the oxygen-dependent reactivity of de novo Due Ferri proteinsNature Chemistry, 4
Lee Solomon, Matthew Sykes, Yimin Wu, R. Schaller, R. Schaller, G. Wiederrecht, H. Fry (2017)
Tailorable Exciton Transport in Doped Peptide-Amphiphile Assemblies.ACS nano, 11 9
Edmund Palermo, Satyavani Vemparala, K. Kuroda (2012)
Cationic spacer arm design strategy for control of antimicrobial activity and conformation of amphiphilic methacrylate random copolymers.Biomacromolecules, 13 5
R. Cheng, Prashant Girinath, Raheel Ahmad (2007)
Effect of lysine side chain length on intra-helical glutamate--lysine ion pairing interactions.Biochemistry, 46 37
S. Solomon, Kristen Oliver (2014)
Antibiotic resistance threats in the United States: stepping back from the brink.American family physician, 89 12
K. Kuroda, Gregory Caputo (2013)
Antimicrobial polymers as synthetic mimics of host-defense peptides.Wiley interdisciplinary reviews. Nanomedicine and nanobiotechnology, 5 1
Jung-ho Lee, Jae Lee, Y. Lee, K. Nam (2013)
Protein/peptide based nanomaterials for energy application.Current opinion in biotechnology, 24 4
Qian Peng, J. Moan, George Farrants, H. Danielsen, C. Rimington (1990)
Localization of potent photosensitizers in human tumor LOX by means of laser scanning microscopy.Cancer letters, 58 1-2
Amphiphilic alpha‐helices are common motifs used in numerous biological systems including membrane channels/pores and antimicrobial peptides (AMPs), and binding proteins, and a variety of synthetic biomaterials. Previously, an amphiphilic peptide with lysine‐containing motifs was shown to reversibly bind the anionic porphyrin meso‐Tetra(4‐sulfonatophenyl)porphyrin (TPPS42−) and promote the formation of excitonically coupled conductive J‐aggregates. The work presented here focuses on the use of this amphiphilic peptide and derivatives as a potential antimicrobial agent. AMPs are naturally occurring components of the innate immune system, which selectively target and kill bacteria. Sequence derivatives were synthesized in which the position of the Trp, used as a fluorescence reporter, was changed. Additional variants were synthesized where the hydrophobic amino acids were replaced with Ala to reduce net hydrophobicity or where the cationic Lys residues were replaced with diaminopropionic acid (Dap). All peptide sequences retained the ability to bind TPPS42− and promote the formation of J‐aggregates. The peptides all exhibited a preference for binding anionic lipid vesicles compared to zwitterionic bilayers. The Trp position did not impact antimicrobial activity, but the substituted peptides exhibited markedly lower efficacy. The Dap‐containing peptide was only active against E. coli and P. aeruginosa, while the Ala‐substituted peptide was inactive at the concentrations tested. This trend was also evident in bacterial membrane permeabilization. The results indicate that the amphiphilic porphyrin binding peptides can also be used as antimicrobial peptides. The cationic nature is a driver in binding to lipid bilayers, but the overall hydrophobicity is important for antimicrobial activity and membrane disruption.
Peptide Science – Wiley
Published: Jul 1, 2018
Keywords: antimicrobial peptides; fluorescence; lipid binding; membrane permeabilization; porphyrin binding
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