Antimicrobial action of prototypic amphipathic cationic decapeptides and their branched dimers

Biochemistry

Volumn 48, Issue 24, 2009, Pages 5642-5657

  Dewan, Pooja C ^a,b   Anantharaman, Aparna ^a   Chauhan, Virander S ^a   Sahal, Dinkar ^a  

^a INTERNATIONAL CENTRE FOR GENETIC ENGINEERING AND BIOTECHNOLOGY   (Italy)

^b INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOISOBUTYRIC ACID; AMPHIPATHIC; ANTIMICROBIAL ACTION; ANTIMICROBIAL PEPTIDE; BACTERIAL CELLS; BACTERIOSTATIC; DE NOVO DESIGN; E. COLI; INNER MEMBRANES; KINETICS EXPERIMENTS; LINEAR DIMERS; LIPOPOLYSACCHARIDE; MINIMUM INHIBITORY CONCENTRATION; MODE OF ACTION; OUTER MEMBRANE; POTENT ACTIVITY; REVERSE PHASE HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY; S. AUREUS; STAPHYLOCOCCUS AUREUS;

ACTIVATION ANALYSIS; AMINES; AMINO ACIDS; ANTIBIOTICS; BIOMATERIALS; CHROMATOGRAPHIC ANALYSIS; DIMERS; DYES; ESCHERICHIA COLI; GROWTH KINETICS; HIGH PRESSURE LIQUID CHROMATOGRAPHY; MEMBRANES; PEPTIDES; POLYPEPTIDES; POLYSACCHARIDES;

CELL MEMBRANES;

2 AMINO 2 METHYLPROPIONIC ACID; BACTERIUM LIPOPOLYSACCHARIDE; DIMER; GLYCYLDIDEHYDROPHENYLALANINEARGINYLLYSINE ALPHA AMINOISOBUTYRIC ACID HISTIDYLLYSYLPHENYLALANYLTRYPTOPHYLALANIMIDE; LYSINE; PHENYLALANINE; POLYPEPTIDE ANTIBIOTIC AGENT; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIAL CELL; BACTERIAL GROWTH; BACTERIOSTASIS; CELL PERMEABILIZATION; CONTROLLED STUDY; DIMERIZATION; DRUG DESIGN; DRUG POTENCY; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HUMAN; HUMAN CELL; KINETICS; MEMBRANE PERMEABILITY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STAPHYLOCOCCUS AUREUS;

ANTI-BACTERIAL AGENTS; ANTIMICROBIAL CATIONIC PEPTIDES; CELL MEMBRANE PERMEABILITY; CYTOSOL; DIMERIZATION; ESCHERICHIA COLI; HELA CELLS; HUMANS; KINETICS; MICROSCOPY, ELECTRON, SCANNING; MICROSCOPY, FLUORESCENCE; OLIGOPEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; NEGIBACTERIA; POSIBACTERIA; STAPHYLOCOCCUS AUREUS;

EID: 67649199172     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi900272r     Document Type: Article

References (41)

1. Tomasz, A. (2006) Microbiology: Weapons of microbial drug resistance abound in soil flora. Science 311, 342-343. (Pubitemid 43132648)
2. D'Costa, V. M., McGrann, K. M., Hughes, D. W., and Wright, G. D. (2006) Sampling the antibiotic resistome. Science 311, 374-377. (Pubitemid 43132661)
3. Bulet, P., Stocklin, R., and Menin, L. (2004) Anti-microbial peptides: From invertebrates to vertebrates. Immunol. Rev. 198, 169-184.
4. Hancock, R. E., and Sahl, H. G. (2006) Antimicrobial and host-defense peptides as new anti-infective therapeutic strategies. Nat. Biotechnol. 24, 1551-1557.
5. Ahmad, A., Yadav, S. P., Asthana, N., Mitra, K., Srivastava, S. P., and Ghosh, J. K. (2006) Utilization of an amphipathic leucine zipper sequence to design antibacterial peptides with simultaneous modulation of toxic activity against human red blood cells. J. Biol. Chem. 281, 22029-22038.
6. Hilpert, K., Volkmer-Engert, R., Walter, T., and Hancock, R. E. (2005) High-throughput generation of small antibacterial peptides with improved activity. Nat. Biotechnol. 23, 1008-1012.
7. Fernandez-Lopez, S., Kim, H. S., Choi, E. C., Delgado, M., Granja, J. R., Khasanov, A., Kraehenbuehl, K., Long, G., Weinberger, D. A., Wilcoxen, K. M., and Ghadiri, M. R. (2001) Antibacterial agents based on the cyclic D,L-α-peptide architecture. Nature 412, 452-455. (Pubitemid 32702711)
8. Giangaspero, A., Sandri, L., and Tossi, A. (2001) Amphipathic α helical antimicrobial peptides. A systematic study of the effects of structural and physical properties on biological activity. Eur. J. Biochem. 268, 5589-5600.
9. Peschel, A. (2002) How do bacteria resist human antimicrobial peptides?. Trends Microbiol. 10, 179-186. (Pubitemid 34242955)
10. Brogden, K. A. (2005) Antimicrobial peptides: Pore formers or metabolic inhibitors in bacteria?. Nat. Rev. Microbiol. 3, 238-250.
11. McAuliffe, O., Ross, R. P., and Hill, C. (2001) Lantibiotics: Structure, biosynthesis and mode of action. FEMS Microbiol. Rev. 25, 285-308.
12. Tam, J. P., Lu, Y. A., and Yang, J. L. (2002) Antimicrobial dendrimeric peptides. Eur. J. Biochem. 269, 923-932.
13. Liu, Z., Deshazer, H., Rice, A. J., Chen, K., Zhou, C., and Kallenbach, N. R. (2006) Multivalent antimicrobial peptides from a reactive polymer scaffold. J. Med. Chem. 49 (12), 3436-3439.
14. Arnusch, C. J., Branderhorst, H., De Kruijff, B., Liskamp, R. M. J., Breukink, E., and Pieters, R. J. (2007) Enhanced membrane pore information by multimeric/oligomeric antimicrobial peptides. Biochemistry 46, 13437-13442. (Pubitemid 350136382)
15. Ramagopal, U. A., Ramakumar, S., Sahal, D., and Chauhan, V. S. (2001) De novo design and characterization of an apolar helical hairpin peptide at atomic resolution: Compaction mediated by weak interactions. Proc. Natl. Acad. Sci. U.S.A. 98, 870-874.
16. Kaiser, E., Colescott, R. L., Bossinger, C. D., and Cook, P. I. (1970) Color Test for Detection of Free Terminal Amino Groups in the Solid-Phase Synthesis of Peptides. Anal. Biochem. 34, 595-598.
17. Steinberg, D. A., Hurst, M. A., Fujii, C. A., Kung, A. H. C., Ho, J. F., Cheng, F. C., Loury, D. J., and Fiddes, J. C. (1997) Protegrin-1: A broad-spectrum, rapidly microbicidal peptide with in vivo activity. Antimicrob. Agents Chemother. 41, 1738-1742.
18. Manhong, W., and Hancock, R. E. W. (1999) Interaction of the Cyclic Antimicrobial Cationic Peptide Bactenecin with the Outer and Cytoplasmic Membrane. J. Biol. Chem. 274, 29-35.
19. Shin, S. Y., Kang, J. H., and Hahm, K. S. (1999) Structure-antibacterial, antitumor and hemolytic activity relationships of cecropin A-magainin 2 and cecropin A-melittin hybrid peptides. J. Pept. Res. 53, 82-90.
20. Hancock, R. E. W., Farmer, S. W., Li, Z., and Poole, K. (1991) Interaction of aminoglycosides with the outer membranes and purified lipopolysaccharide and OmpF porin of Escherichia coli. Antimicrob. Agents Chemother. 35, 1309-1314.
21. Hayat, M. A. (1981) Principle and Techniques of Electron Microscopy: Biological Applications , Edward Arnold, London.
22. Mosmann, T. (1983) Rapid colorimetic assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 65, 33-55.
23. Venkatraman, J., Shankaramma, S. C., and Balaram, P. (2001) Design of folded peptides. Chem. Rev. 101, 3131-3152.
24. Mathur, P., Ramakumar, S., and Chauhan, V. S. (2004) Peptide design using α,β-dehydro amino acids: From β-turns to helical hairpins. Biopolymers 76, 150-161. (Pubitemid 38529430)
25. Rudresh, Ramakumar, S., Ramagopal, U. A., Inai, Y., Goel, S., Sahal, D., and Chauhan, V. S. (2004) De novo design and characterization of a helical hairpin eicosapeptide: Emergence of an anion receptor in the linker region. Structure 12, 389-396. (Pubitemid 38353060)
26. Sudha, T. S., Vijayakumar, E. K., and Balaram, P. (1983) Circular dichroism studies of helical oligopeptides. Can 3(10) and α-helical conformations be chiroptically distinguished?. Int. J. Pept. Protein Res. 22, 464-468.
27. Formaggio, F., Crisma, M., Rossi, P., Scrimin, P., Kaptein, B., Broxterman, Q. B., Kamphuis, J., and Toniolo, C. (2000) The first water-soluble 3(10)-helical peptides. Chemistry 6, 4498-4504. (Pubitemid 32047059)
28. Yeaman, M. R., and Yount, N. Y. (2003) Mechanisms of antimicrobial peptide action and resistance. Pharmacol. Rev. 55, 27-55.
29. Raetz, C. R., and Whitfield, C. (2002) Lipopolysaccharide endotoxins. Annu. Rev. Biochem. 71, 635-700.
30. Nikaido, H. (2003) Molecular basis of bacterial outer membrane permeability revisited. Microbiol. Mol. Biol. Rev. 67, 593-656.
31. Hancock, R. E., Farmer, S. W., Li, Z. S., and Poole, K. (1991) Interaction of aminoglycosides with the outer membranes and purified lipopolysaccharide and OmpF porin of Escherichia coli. Antimicrob. Agents Chemother. 35, 1309-1314.
32. Boulos, L., Prevost, M., Barbeau, B., Coallier, J., and Desjardins, R. (1999) LIVE/DEAD BacLight: Application of a new rapid staining method for direct enumeration of viable and total bacteria in drinking water. J. Microbiol. Methods 37, 77-86. (Pubitemid 29248770)
33. Bracci, L., Falciani, C., Lelli, B., Lozzi, L., Runci, Y., Pini, A., De Montis, M. G., Tagliamonte, A., and Neri, P. (2003) Synthetic peptides in the form of dendrimers become resistant to protease activity. J. Biol. Chem. 278, 46590-46595.
34. Ulmschneider, M. B., and Sansom, M. S. (2001) Amino acid distributions in integral membrane protein structures. Biochim. Biophys. Acta 1512, 1-14.
35. Russell, A. D. (2002) Mechanisms of antimicrobial action of antiseptics and disinfectants: An increasingly important area of investigation. J. Antimicrob. Chemother. 49, 597-599.
36. Stratton, C. W. (2003) Dead bugs don't mutate: Susceptibility issues in the emergence of bacterial resistance. Emerging Infect. Dis. 9, 10-16.
37. Brogden, K. A., De Lucca, A. J., Bland, J., and Elliott, S. (1996) Isolation of an ovine pulmonary surfactant-associated anionic peptide bactericidal for Pasteurella haemolytica. Proc. Natl. Acad. Sci. U.S.A. 93, 412-416.
38. O'Farrell, P. Z., Goodman, H. M., and O'Farrell, P. H. (1977) High resolution two-dimensional electrophoresis of basic as well as acidic proteins. Cell 12, 1133-1141.
39. Svenson, J., Stensen, W., Brandsdal, B., Haug, B., Monrad, J., and Svendsen, J. (2008) Antimicrobial Peptides with Stability toward Tryptic Degradation. Biochemistry 47 (12), 3777-3788.
40. Schafmeister, C. E., Gregory, J. P., and Verdine, G. L. (2000) An All-Hydrocarbon Cross-Linking System for Enhancing the Helicity and Metabolic Stability of Peptides. J. Am. Chem. Soc. 122, 5891-5892.
41. Weidenmaier, C., and Peschel, A. (2008) Teichoic acids and related cell-wall glycopolymers in Gram-positive physiology and host interactions. Nat. Rev. Microbiol. 6, 276-287.