An Adamantyl Amino Acid Containing GramicidinS Analogue with Broad Spectrum Antibacterial Activity and Reduced Hemolytic Activity

The cyclic cationic antimicrobial peptide gramicidinS (GS) is an effective topical antibacterial agent that is toxic for human red blood cells (hemolysis). Herein, we present a series of amphiphilic derivatives of GS with either two or four positive charges and characteristics ranging between very p...

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Bibliographic Details
Published in:Chemistry : a European journal 2010-10, Vol.16 (40), p.12174-12181
Main Authors: Kapoerchan, Varsha V, Knijnenburg, Annemiek D, Niamat, Miquel, Spalburg, Emile, deNeeling, Albert J, Nibbering, Peter H, Mars-Groenendijk, Roos H, Noort, Daan, Otero, Jose M, Llamas-Saiz, Antonio L, vanRaaij, Mark J, vanderMarel, Gijs A, Overkleeft, Herman S, Overhand, Mark
Format: Article
Language:English
Subjects:
Amino acids
Antiinfectives and antibacterials
Bacteria
Cationic
Chemistry
Derivatives
Erythrocytes
Gram-positive bacteria
MRSA
Peptides
Toxicity
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Summary:The cyclic cationic antimicrobial peptide gramicidinS (GS) is an effective topical antibacterial agent that is toxic for human red blood cells (hemolysis). Herein, we present a series of amphiphilic derivatives of GS with either two or four positive charges and characteristics ranging between very polar and very hydrophobic. Screening of this series of peptide derivatives identified a compound that combines effective antibacterial activity with virtually no toxicity within the same concentration range. This peptide acts against both Gram-negative and Gram-positive bacteria, including several MRSA strains, and represents an interesting lead for the development of a broadly applicable antibiotic.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201001686