What Goes around Comes around-A Comparative Study of the Influence of Chemical Modifications on the Antimicrobial Properties of Small Cyclic Peptides
Abstract
:1. Introduction
2. Experimental Section
2.1. Materials
2.2. Peptide Synthesis
2.3. CD Spectroscopy
2.4. Hydrophobicity
2.5. Antimicrobial Activity
2.6. Hemolytic Activity
2.7. Propidium Iodide Influx
2.8. Cellular Uptake
3. Results and Discussion
3.1. Peptide Modifications and Antimicrobial Activity
Peptides | Sequences | MIC [µM] | Hemolysis [%]
at 100 µM | |
---|---|---|---|---|
E. coli DH5α | B. subtilis DSM 347 | |||
cWFW | c-RRRWFW | 3 | 3 | 4 |
cW2[Fluos] | c-RRRWWK[Fluos] | >100 | >100 | 9 |
cW3[Fluos] | c-RRWWWK[Fluos] | >100 | >100 | 2 |
cW[Cu]W | c-RRRW[Ala-Coumarin]W | 25 | 6 | 23 |
cW[S-Cu]W | c-RRRW[Cys-Br-Coumarin]W | 25 | 6 | 76 |
cW[NBD]W | c-RRRW[Dap-NBD]W | 50 | 25 | 76 |
cRKR | c-RKRWFW | 50 | 12 | 4 |
cRKK | c-RKKWFW | 50 | 25 | 56 |
cKRK | c-KRKWFW | 12 | 25 | 2 |
cKKR | c-KKRWFW | 100 | 25 | 3 |
cKKK | c-KKKWFW | 100 | 50 | 8 |
cR2[Cu] | c-KRKW[Ala-Coumarin]W | 50 | 6 | 4 |
cR2[S-Cu] | c-KRKW[Cys-Br-Coumarin]W | 50 | 25 | 5 |
cR2[NBD] | c-KRKW[Dap-NBD]W | 50 | 12 | 26 |
3.2. Peptide Hydrophobicity and Conformation
3.3. Mode of Antimicrobial Action
4. Conclusions
Acknowledgments
Conflicts of Interest
References
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Scheinpflug, K.; Nikolenko, H.; Komarov, I.V.; Rautenbach, M.; Dathe, M. What Goes around Comes around-A Comparative Study of the Influence of Chemical Modifications on the Antimicrobial Properties of Small Cyclic Peptides. Pharmaceuticals 2013, 6, 1130-1144. https://doi.org/10.3390/ph6091130
Scheinpflug K, Nikolenko H, Komarov IV, Rautenbach M, Dathe M. What Goes around Comes around-A Comparative Study of the Influence of Chemical Modifications on the Antimicrobial Properties of Small Cyclic Peptides. Pharmaceuticals. 2013; 6(9):1130-1144. https://doi.org/10.3390/ph6091130
Chicago/Turabian StyleScheinpflug, Kathi, Heike Nikolenko, Igor V. Komarov, Marina Rautenbach, and Margitta Dathe. 2013. "What Goes around Comes around-A Comparative Study of the Influence of Chemical Modifications on the Antimicrobial Properties of Small Cyclic Peptides" Pharmaceuticals 6, no. 9: 1130-1144. https://doi.org/10.3390/ph6091130