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J Am Chem Soc. 2012 Jul 11;134(27):11088-91. doi: 10.1021/ja303304j. Epub 2012 Jun 27.

Synthetic mimics of antimicrobial peptides with immunomodulatory responses.

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1
Department of Polymer Science and Engineering, University of Massachusetts, Amherst, Massachusetts 01003, USA.

Abstract

A new series of aryl-based synthetic mimics of antimicrobial peptides (SMAMPs) with antimicrobial activity and selectivity have been developed via systematic tuning of the aromatic groups and charge. The addition of a pendant aromatic group improved the antimicrobial activity against Gram-negative bacteria, while the addition of charge improved the selectivity. SMAMP 4 with six charges and a naphthalene central ring demonstrated a selectivity of 200 against both Staphylococcus aureus and Escherichia coli , compared with a selectivity of 8 for the peptide MSI-78. In addition to the direct antimicrobial activity, SMAMP 4 exhibited specific immunomodulatory activities in macrophages both in the presence and in the absence of lipopolysaccharide, a TLR agonist. SMAMP 4 also induced the production of a neutrophil chemoattractant, murine KC, in mouse primary cells. This is the first nonpeptidic SMAMP demonstrating both good antimicrobial and immunomodulatory activities.

PMID:
22697149
PMCID:
PMC3406751
DOI:
10.1021/ja303304j
[Indexed for MEDLINE]
Free PMC Article
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