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Rational Design of Tryptophan-Rich Antimicrobial Peptides with Enhanced Antimicrobial Activities and Specificities
Journal article   Peer reviewed

Rational Design of Tryptophan-Rich Antimicrobial Peptides with Enhanced Antimicrobial Activities and Specificities

Hui-Yuan Yu-, Kuo-Chun Huang-, Bak-Sau Yip-, Chih-Hsiang Tu, Heng-Li Chen, Hsi-Tsung Cheng and Jya-Wei Cheng
ChemBioChem, Vol.11(16), pp.2273-2282
02/11/2010

Abstract

Antibiotics Drug design Membranes Peptides Structure-activity relationships
Trp-rich antimicrobial peptides play important roles in the host innate defense mechanism of many plants and animals. A series of short Trp-rich peptides derived from the C-terminal region of Bothrops asper myothoxin II, a Lys49 phospholipase A 2 (PLA 2 ), were found to reproduce the antimicrobial activities of their parent molecule. Of these peptides, KKWRWWLKALAKK-designated PEM-2-was found to display improved activity against both Gram-positive and Gram-negative bacteria. To improve the antimicrobial activity of PEM-2 for potential clinical applications further, we determined the solution structure of PEM-2 bound to membrane-mimetic dodecylphosphocholine (DPC) micelles by two-dimensional NMR methods. The DPC micelle-bound structure of PEM-2 adopts an Α-helical conformation and the positively charged residues are clustered together to form a hydrophilic patch. The surface electrostatic potential map indicates that two of the three tryptophan residues are packed against the peptide backbone and form a hydrophobic face with Leu7, Ala9, and Leu10. A variety of biophysical and biochemical experiments, including circular dichroism, fluorescence spectroscopy, and microcalorimetry, were used to show that PEM-2 interacted with negatively charged phospholipid vesicles and efficiently induced dye release from these vesicles, suggesting that the antimicrobial activity of PEM-2 could be due to interactions with bacterial membranes. Potent analogues of PEM-2 with enhanced antimicrobial and less pronounced hemolytic activities were designed with the aid of these structural studies.Systematic variation: The positions of tryptophan residues in an antimicrobial peptide were systematically varied according to structure-activity studies. Trp-rich antimicrobial peptides based on the solution structure and interactions of model membranes of the parent peptide PEM-2 were designed. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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