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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Weir, Ron / Stohner, Jürgen

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1365-3075
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Influence of C-terminal amidation on the antimicrobial and hemolytic activities of cationic α-helical peptides

Erik Strandberg
  • Institute for Biological Interfaces, Forschungszentrum Karlsruhe, Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany
/ Deniz Tiltak
  • Institute of Organic Chemistry, University of Karlsruhe, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
/ Marco Ieronimo
  • Institute of Organic Chemistry, University of Karlsruhe, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
/ Nathalie Kanithasen
  • Institute of Organic Chemistry, University of Karlsruhe, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
/ Parvesh Wadhwani
  • Institute for Biological Interfaces, Forschungszentrum Karlsruhe, Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany
/ Anne S. Ulrich
  • Institute for Biological Interfaces, Forschungszentrum Karlsruhe, Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany
Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/pac200779040717

The effect of C-terminal amidation on the antimicrobial and hemolytic activities of antimicrobial peptides was studied using three cationic peptides which form amphiphilic α-helices when bound to membranes. The natural antimicrobial peptide PGLa, the designer-made antibiotic MSI-103, and the cell-penetrating "model amphipathic peptide" (MAP) are all amidated in their original forms, and their biological activities were compared with the same sequences carrying a free C-terminus. It was found that, in general, a free COOH-terminus reduces both the antimicrobial activity and the hemolytic side effects of the peptides. The only exception was observed for MSI-103, whose antimicrobial activity was not decreased in the acid form. Having shown that the therapeutic index (TI) of this novel peptide is significantly higher than for the other tested peptides, with high antibiotic activity and little undesired effects, we suggest that it could be a useful starting point for further development of new peptide antibiotics.

Keywords: amphipathic peptides; antimicrobial peptides; biological assays; cationic α-helices; C-terminal modifications; designed peptide antibiotics

Conference

International Symposium on Chemistry of Natural Products (ISCNP-25) and 5th International Conference on Biodiversity (ICOB-5), International Conference on Biodiversity, International Symposium on the Chemistry of Natural Products, ICOB, ISCNP, Biodiversity, Natural Products, 25th, Kyoto, Japan, 2006-07-23–2006-07-28


Published Online: 2009-01-01

Published in Print: 2007-01-01


Citation Information: Pure and Applied Chemistry. Volume 79, Issue 4, Pages 717–728, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac200779040717, January 2009

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[2]
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Sabine Reißer, Erik Strandberg, Thomas Steinbrecher, and Anne S. Ulrich
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[8]
S Melzer, LS Davis, and PJ Bishop
New Zealand Journal of Zoology, 2012, Volume 39, Number 4, Page 329
[10]
Jochen Bürck, Siegmar Roth, Parvesh Wadhwani, Sergii Afonin, Nathalie Kanithasen, E. Strandberg, and Anne S. Ulrich
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Erik Strandberg, Deniz Tiltak, Sebastian Ehni, Parvesh Wadhwani, and Anne S. Ulrich
Biochimica et Biophysica Acta (BBA) - Biomembranes, 2012, Volume 1818, Number 7, Page 1764
[12]
Frederick Harris, Sarah R. Dennison, Jaipaul Singh, and David A. Phoenix
Medicinal Research Reviews, 2013, Volume 33, Number 1, Page 190
[13]
Raymond M. Dawson and Chun-Qiang Liu
International Journal of Antimicrobial Agents, 2011, Volume 37, Number 5, Page 432
[14]
Raymond M. Dawson, Jane McAllister, and Chun-Qiang Liu
International Journal of Antimicrobial Agents, 2010, Volume 36, Number 4, Page 359
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[16]
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Biochimica et Biophysica Acta (BBA) - Biomembranes, 2009, Volume 1788, Number 8, Page 1656
[17]
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