Abstract
A combinatorial approach has been used to rapidly identify cyclic D,L-α-peptide hexamer sequences that exert biocidal activity towards both methicillin-resistant Staphylococcus aureus (MRSA) and E. coli bacteria, as well as the marine algae Ulva linza and Navicula perminuta. Evaluation of the effects against marine algae was facilitated by the development of a reliable, automated assay for toxicity, which should be of general utility for biofouling investigations. While the selective toxicity of cyclic D,L-α-peptides towards bacteria has been proven to be highly sensitive to minor changes in amino acid composition, this study demonstrates that this phenomenon extends to eukaryotic species as well, despite their significant structural differences. In performing toxicity assays on both prokaryotic and eukaryotic organisms in parallel, we have discovered examples of six-residue cyclic D,L-α-peptide sequences with either broad-spectrum or highly selective biocidal activities. Sequence [KWFFFH] (underlined amino acid abbreviations represent D-amino acid residues) was found to display 100-fold selectivity towards U. linza, demonstrating that the approach described herein may help lead to the development of new biofouling tools which are not generally toxic to all organisms, but rather specifically target microbial agents of interest.
| Original language | English |
|---|---|
| Pages (from-to) | 4008-4013 |
| Number of pages | 6 |
| Journal | Chemistry - A European Journal |
| Volume | 13 |
| Issue number | 14 |
| DOIs | |
| State | Published - 2007 |
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All Science Journal Classification (ASJC) codes
- Chemistry(all)
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A combinatorial approach to the discovery of biocidal six-residue cyclic D,L-α-peptides against the bacteria methicillin-resistant Staphylococcus aureus (MRSA) and E. coli and the biofouling algae Ulva linza and Navicula perminuta. / Fletcher, James T.; Finlay, John A.; Callow, Maureen E.; Cailow, James A.; Ghadiri, M. Reza.
In: Chemistry - A European Journal, Vol. 13, No. 14, 2007, p. 4008-4013.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - A combinatorial approach to the discovery of biocidal six-residue cyclic D,L-α-peptides against the bacteria methicillin-resistant Staphylococcus aureus (MRSA) and E. coli and the biofouling algae Ulva linza and Navicula perminuta
AU - Fletcher, James T.
AU - Finlay, John A.
AU - Callow, Maureen E.
AU - Cailow, James A.
AU - Ghadiri, M. Reza
PY - 2007
Y1 - 2007
N2 - A combinatorial approach has been used to rapidly identify cyclic D,L-α-peptide hexamer sequences that exert biocidal activity towards both methicillin-resistant Staphylococcus aureus (MRSA) and E. coli bacteria, as well as the marine algae Ulva linza and Navicula perminuta. Evaluation of the effects against marine algae was facilitated by the development of a reliable, automated assay for toxicity, which should be of general utility for biofouling investigations. While the selective toxicity of cyclic D,L-α-peptides towards bacteria has been proven to be highly sensitive to minor changes in amino acid composition, this study demonstrates that this phenomenon extends to eukaryotic species as well, despite their significant structural differences. In performing toxicity assays on both prokaryotic and eukaryotic organisms in parallel, we have discovered examples of six-residue cyclic D,L-α-peptide sequences with either broad-spectrum or highly selective biocidal activities. Sequence [KWFFFH] (underlined amino acid abbreviations represent D-amino acid residues) was found to display 100-fold selectivity towards U. linza, demonstrating that the approach described herein may help lead to the development of new biofouling tools which are not generally toxic to all organisms, but rather specifically target microbial agents of interest.
AB - A combinatorial approach has been used to rapidly identify cyclic D,L-α-peptide hexamer sequences that exert biocidal activity towards both methicillin-resistant Staphylococcus aureus (MRSA) and E. coli bacteria, as well as the marine algae Ulva linza and Navicula perminuta. Evaluation of the effects against marine algae was facilitated by the development of a reliable, automated assay for toxicity, which should be of general utility for biofouling investigations. While the selective toxicity of cyclic D,L-α-peptides towards bacteria has been proven to be highly sensitive to minor changes in amino acid composition, this study demonstrates that this phenomenon extends to eukaryotic species as well, despite their significant structural differences. In performing toxicity assays on both prokaryotic and eukaryotic organisms in parallel, we have discovered examples of six-residue cyclic D,L-α-peptide sequences with either broad-spectrum or highly selective biocidal activities. Sequence [KWFFFH] (underlined amino acid abbreviations represent D-amino acid residues) was found to display 100-fold selectivity towards U. linza, demonstrating that the approach described herein may help lead to the development of new biofouling tools which are not generally toxic to all organisms, but rather specifically target microbial agents of interest.
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U2 - 10.1002/chem.200601583
DO - 10.1002/chem.200601583
M3 - Article
VL - 13
SP - 4008
EP - 4013
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 14
ER -