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Antimicrobial Agents and Chemotherapy, February 2007, p. 597-603, Vol. 51, No. 2
0066-4804/07/$08.00+0     doi:10.1128/AAC.00828-06
Copyright © 2007, American Society for Microbiology. All Rights Reserved.

Length Effects in Antimicrobial Peptides of the (RW)n Series{triangledown}

Zhigang Liu,1 Anna Brady,2 Anne Young,1 Brian Rasimick,3 Kang Chen,1 Chunhui Zhou,1 and Neville R. Kallenbach1*

Department of Chemistry, New York University, New York, New York 10003,1 Department of Biochemistry and Molecular Biology, University of Chicago, Chicago, Illinois 60637,2 Essential Dental Systems, Inc., South Hackensack, New Jersey 076063

Received 9 July 2006/ Returned for modification 1 September 2006/ Accepted 1 November 2006

A class of antimicrobial peptides involved in host defense consists of sequences rich in Arg and Trp-R and -W. Analysis of the pharmacophore in these peptides revealed that chains as short as trimers of sequences such as WRW and RWR have antimicrobial activity (M. B. Strom, B. E. Haug, M. L. Skar, W. Stensen, T. Stiberg, and J. S. Svendsen, J. Med. Chem. 46:1567-1570, 2003). To evaluate the effect of chain length on antimicrobial activity, we synthesized a series of peptides containing simple sequence repeats, (RW)n-NH2 (where n equals 1, 2, 3, 4, or 5), and determined their antimicrobial and hemolytic activity. The antimicrobial activity of the peptides increases with chain length, as does the hemolysis of red blood cells. Within the experimental error, longer peptides (n equals 3, 4, or 5) show similar values for the ratio of hemolytic activity to antibacterial activity, or the hemolytic index. The (RW)3 represents the optimal chain length in terms of the efficacy of synthesis and selectivity as evaluated by the hemolytic index. Circular dichroism spectroscopy indicates that these short peptides appear to be unfolded in aqueous solution but acquire structure in the presence of phospholipids. Interaction of the peptides with model lipid vesicles was examined using tryptophan fluorescence. The (RW)n peptides preferentially interact with bilayers containing the negatively charged headgroup phosphatidylglycerol relative to those containing a zwitterionic headgroup, phosphatidylcholine.

* Corresponding author. Mailing address: Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003. Phone: (212) 998-8757. Fax: (212) 260-7905. E-mail:nrk1{at}nyu.edu.

{triangledown} Published ahead of print on 4 December 2006.

Antimicrobial Agents and Chemotherapy, February 2007, p. 597-603, Vol. 51, No. 2
0066-4804/07/$08.00+0     doi:10.1128/AAC.00828-06
Copyright © 2007, American Society for Microbiology. All Rights Reserved.



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